Thursday, July 14, 2011



JCT examines tax treatment of business debt

JCX-41-11, Present Law And Background Relating To Tax Treatment Of Business Debt


Due to growing concern about the level of corporate debt (along with household and Federal debt), the Joint Committee on Taxation (JCT) has released a report on the Federal tax rules on the use of debt leverage by businesses in the U.S. From '87 to 2010, corporate debt, as a percentage of gross national product (GNP), has risen from 42.8% to 48.3%, a significant increase (although less dramatic than the 57.9% to 90.2% increase in household debt and the 41% to 63.2% increase in Federal debt).

Background on issuer treatment of debt and equity. In general, interest paid or accrued by a business is deductible under Code Sec. 163(a) , subject to a number of limitations. Interest generally is deducted as it is paid or accrues. But, original issue discount (OID) interest (where the amount to be paid at the maturity of a debt instrument exceeds the issue price by more than a de minimis amount) is deducted in advance of actual payment or other accrual under the terms of the instrument. ( Code Sec. 163(e) )

Dividends or other returns on equity aren't deductible. The issuance of a debt or equity instrument for cash is not a taxable event to the issuer. Purchased assets generally have a cost basis for purposes of determining deprecation or gain or loss on sale, regardless of whether the purchase was financed with debt (including nonrecourse debt) or equity. If dividends are not paid on equity, or the capital contributed by an equity holder isn't returned, there is generally no taxable income, gain, or other consequence to the issuer.

If debt is cancelled, modified, or repurchased, the borrower generally realizes income from the discharge of indebtedness. Exceptions to this income inclusion are provided for bankruptcy and insolvency, other situations including seller financing of purchased property, qualified farm indebtedness, qualified real property business indebtedness, and contributions of debt by an equity holder. The exceptions usually require the taxpayer to reduce the basis of property, or to reduce tax attributes such as net operating losses. A significant modification of a debt instrument is treated as the disposition of the old instrument in exchange for the new instrument.

If nonrecourse debt is satisfied by foreclosure on the assets securing the debt, the borrower generally realizes gain from the disposition of the assets for the amount of the debt (even if the assets are not worth that amount).

Background on holder treatment of debt and equity. Interest on debt is taxed to a taxable individual or corporate holder at the ordinary income tax rate of the holder (currently, up to 35%). Dividends paid by a taxable C corporation are generally taxed to an individual shareholder at a maximum rate of 15%. Dividends are generally taxed to a C corporation shareholder at a maximum rate of 10.5% (or less, depending on the percentage ownership the corporate shareholder has in the issuing corporation). Gain on the sale of an equity interest in a C corporation or in an S corporation is generally capital gain. If the stock has been held for at least one year, such gain is generally taxable to an individual shareholder at a maximum rate of 15%. Gain on the sale of C corporation stock is taxed to a corporate shareholder at regular corporate rates (generally 35%). Gain on the sale of an equity interest in a partnership is also generally capital gain of the partner, except for amounts attributable to unrealized receivables and inventory items of the partnership, which are taxable as ordinary income. Interest is generally taxable when paid or accrued.

Interest is generally includable in income and taxable before any cash payment if the OID rules apply. Dividends are generally not taxable until paid. However, in limited circumstances, certain preferred stock dividends may be accrued under rules similar to the rules for debt. A shareholder may also be treated as having received a dividend if his percentage of stock ownership increases as a result of the payment of dividends to other shareholders.

A tax-exempt investor is generally not taxed on investment interest, subject to certain unrelated business income tax rules for debt-financed income. Although U.S.-source interest paid to a foreign investor is generally subject to a 30% withholding tax, various exceptions exist in the Code and in Treaties.

JCT's analysis. The JCT Report concludes that the Federal income tax treatment of debt and equity creates incentives to utilize one or the other depending on the tax characteristics of the issuer and of the particular investor. Taxpayers have considerable flexibility to design instruments treated as either debt or equity but which blend features traditionally associated with both. In general, a corporate issuer isn't subject to corporate tax on amounts that it deducts as interest on debt. On the other hand, dividends, which aren't deductible by the payor, come out of the corporation's after-tax income.

Debt instruments can allow the accrual of the interest deduction along with the inclusion in income by the holder at a time before the payment of cash. Interest income may be taxed at a higher rate to a taxable holder than the holder's dividends or capital gains attributable to corporate retained earnings (to which lower tax rates currently apply). While some forms of debt investments aren't subject to U.S. tax or are taxed at reduced rates in the hands of a tax-exempt or foreign investor—resulting in tax arbitrage that can shelter otherwise taxable income—special rules in the Code apply in these situations to limit interest deductions.

In some situations, business may have an incentive to borrow. Debt allows owners of business or investment assets to extract cash or obtain a higher basis in the leveraged asset without an additional equity investment. For example, a higher basis in a leveraged asset that is depreciable can increase depreciation deductions.

The discharge or restructuring of debt in the event of financial difficulty can cause the issuer to recognize discharge of indebtedness income or gain with respect to the satisfaction of nonrecourse indebtedness for less than the outstanding amount. The income tax treatment of debt discharge depends on whether the debt is recourse or nonrecourse, the nature of the borrower's assets and of the borrowing, and the circumstances of the restructuring or discharge. In a number of instances, no current income is recognized, though tax attributes such as net operating losses, credits, or the basis of assets may be reduced. On the other hand, the failure to pay dividends or return an equity investment in full doesn't cause income or gain to be recognized by the issuer.

The tax law generally contains no fixed definition of debt or equity. In classifying an instrument as debt or equity, the courts have applied many factors. In general, a debt instrument requires a fixed obligation to pay a certain amount at a specified date. Debt instruments provide for remedies including priorities in bankruptcy in the event of default. Conversely, an instrument designated and respected as equity for tax purposes may have features that are more economically burdensome to the issuer.

Equity can be beneficial for tax purposes in certain cases. Although corporate distributions and sales of corporate stock subject the holder to tax in addition to any tax paid by the corporation, reduced tax rates apply to holders with respect to such distributions or gain. Dividends on corporate equity are largely excludable by corporate holders (currently resulting in a maximum 10.5% tax rate under the 70% dividends received deduction). For individual shareholders, both dividends and capital gains on the sale of corporate stock are generally subject to a maximum 15% rate (compared to the top individual rate of 35%).

Different treatment of an instrument for purposes of financial reporting, for regulatory capital purposes in a regulated industry (such as an insurance or banking), for ratings agency purposes, and under foreign tax and nontax laws, may result in more favorable overall business treatment when combined with the benefits of debt or equity for Federal income tax purposes.















PRESENT LAW AND BACKGROUND RELATING
TO TAX TREATMENT OF BUSINESS DEBT
A REPORT TO THE
JOINT COMMITTEE ON TAXATION
Prepared by the Staff
of the
JOINT COMMITTEE ON TAXATION
July 11, 2011
JCX-41-11 i
CONTENTS
Page
INTRODUCTION AND SUMMARY ........................................................................................... 1
I. PRESENT LAW AND LEGISLATIVE BACKGROUND ........................................................ 5
A. General Rules ...................................................................................................................... 5
1. Issuer treatment of debt and equity ............................................................................... 5
2. Holder treatment of debt and equity ............................................................................. 9
3. Acquisitions and dispositions ..................................................................................... 13
B. Definition of Debt and Equity ........................................................................................... 15
1. Distinguishing debt from equity ................................................................................. 15
2. Regulatory authority pursuant to section 385 ............................................................. 17
C. Rules to Address Stripping of U.S. Corporate Tax Base in the Case of Nontaxed
Holders .............................................................................................................................. 20
1. Earnings stripping ....................................................................................................... 20
2. Tax treatment of certain payments to controlling exempt organizations .................... 23
D. Rules to Address Corporate Base Erosion Without Regard to Holders’ Tax Status ........ 25
1. Corporate Equity Reduction Transactions .................................................................. 25
2. Debt expected to be paid in equity .............................................................................. 27
3. Applicable high-yield discount obligations ................................................................ 28
4. Interest on certain acquisition indebtedness ............................................................... 30
E. Rules to Address Tax Arbitrage in the Case of Borrowing to Fund Untaxed Income ..... 31
1. Interest related to tax-exempt income ......................................................................... 31
2. Debt with respect to certain insurance products ......................................................... 35
3. Debt-financed income of tax-exempt organizations ................................................... 39
4. Dividends received deduction reduction for debt-financed portfolio stock ................ 41
F. Rules to Match Timing of Tax Deduction and Income Inclusion Relating to Debt ......... 43
1. Interest and OID on amounts payable to related foreign lenders ................................ 43
2. Construction period interest ........................................................................................ 45
3. Interest in the case of straddles ................................................................................... 46
G. Other Rules Relating to Business Debt and Equity .......................................................... 48
1. Employee Stock Ownership Plans .............................................................................. 48
2. Nonqualified preferred stock not treated as stock for certain purposes ...................... 52
II. DATA WITH RESPECT TO BUSINESS DEBT .................................................................. 56
III. ECONOMIC INCENTIVES CREATED UNDER PRESENT LAW FOR BUSINESS
DEBT ...................................................................................................................................... 64
A. Incentives Related to Firm Capital Structure .................................................................... 64
1. Tax incentives for debt ................................................................................................ 67
2. Tax incentives related to equity .................................................................................. 78
3. Incentives to create hybrid instruments ...................................................................... 80
4. Incentives to substitute other arrangements for debt .................................................. 85ii
5. Incentives to use leveraged ESOPs ............................................................................. 86
6. Financial accounting and other considerations ........................................................... 90
IV. TAX TREATMENT OF CORPORATE DEBT IN SELECTED COUNTRIES ................... 95
A. Summary ........................................................................................................................... 95
B. Law Library of Congress: Tax Treatment of Corporate Debt .......................................... 971
INTRODUCTION AND SUMMARY
Introduction
This document
1
 has been prepared by the staff of the Joint Committee on Taxation, in
response to the request of the Chairman and Vice Chairman of the Joint Committee on Taxation
for a report of Federal tax rules relating to the use of leverage by households and businesses in
the United States.
2
  
There has been concern about the level of debt in the U.S. economy.  Below is a table
illustrating corporate debt, household debt, and Federal debt as a percentage of gross national
product (GNP), 1987-2010.  This document relates to business debt; corporate data is shown in
column one of Table 1, below.
Table 1.−Corporate Debt, Household Debt, and Federal Debt, as a Percentage
of Gross National Product (GNP), 1987-2010
Year
Corporate Debt
1
as a Percentage of
GNP
Household Debt
2
as a Percentage of
GNP
Federal Debt
3
as a Percentage of
GNP
1987 42.8 57.9 41.0
1990 43.6 61.4 42.8
1995 39.5 65.0 48.9
2000 46.4 69.9 33.9
2005 43.0 92.4 36.9
2010 48.3 90.2 63.2
1
  Corporate debt of nonfinancial C corporations and S corporations excluding farms.
2
  Household debt includes debt of personal trusts, nonprofit organizations, partnerships and sole
proprietorships.
3
  Federal debt excludes federal debt held by Federal agency trust funds.
Sources:  Debt levels from The Board of Governors of the Federal Reserve System Flow of Funds Accounts
of the United States:  Flows and Outstandings First Quarter 2011 Table D.3. GNP levels from the Federal
Reserve Bank of St. Louis. 
The first part of this document presents an overview of Federal income tax rules relating
to debt and equity, and some of the statutory limitations on the benefits of each.  The overview
includes the treatment of issuers as well as holders, and the treatment of each in the event of a
business downturn in which the instrument becomes worthless.  
                                                
1
  This document may be cited as follows:  Joint Committee on Taxation, Present Law and Background
Relating to Tax Treatment of Business Debt (JCX-41-11), July 11, 2011.  This document can be found on our
website at www.jct.gov.   
2
  The request was made at the 112
th
 Congress Organizational Meeting of the Joint Committee on Taxation
on March 15, 2011. 2
The second part of this document presents data regarding nonfinancial business sector
debt and other business debt over several decades.  
The third part of this document describes incentives for debt or equity that exist in the
absence of tax considerations, a discussion of the incentives that may be created by the presentlaw tax treatment of instruments as debt or as equity.   
A companion document
3
 provides economic data with respect to household debt and
provides a description of Federal tax rules governing household debt and economic incentives
under present law.
Summary
Business enterprises and their investors have business reasons to structure capital
investment as either debt or equity.  For example, investors may prefer varying levels of risk. 
Investors may seek different levels of priority in the event of bankruptcy of the business. 
Businesses can issue interests to investors that have varying levels of control over the enterprise
and degrees of participation in profitability or growth of the enterprise. 
The tax law generally contains no fixed definition of debt or equity.  Taxpayers have
considerable flexibility to design instruments treated as either debt or equity but which blend
features traditionally associated with both.    
The Federal income tax treatment of debt and of equity creates incentives to utilize one or
the other depending on the tax characteristics of the issuer and of the particular investor.  In
general, a corporate issuer is not subject to corporate tax on amounts that it deducts as interest on
debt.  By contrast, dividends, which are not deductible by the payor, come out of after-tax
income of the corporation.  
Debt instruments can permit the accrual of the interest deduction along with the inclusion
in income by the holder at a time prior to the payment of cash.  Interest income may be taxed at a
higher rate to a taxable holder than the holder’s dividends or capital gains attributable to
corporate retained earnings (to which lower tax rates currently apply).  However, some forms of
debt investments are not subject to U.S. tax or are taxed at reduced rates in the hands of a taxexempt or foreign investor. A number of special rules in the Code are designed to limit the tax
benefits that can be obtained from interest deductions to protect the corporate tax base. 
To the extent that debt finances assets that produce tax-exempt or otherwise tax-favored
income, the interest deduction is available to offset other income taxed at higher rates.  The
resulting tax arbitrage can shelter otherwise taxable income. A number of special rules in the
Code are directed at limiting this effect. 
                                               
3
  Joint Committee on Taxation, Present Law and Background Relating to Tax Treatment of Household
Debt (JCX-40-11), July 11, 2011 (hereinafter “Tax Treatment of Household Debt”).  This document can be found on
our website at www.jct.gov.  3
In addition to the tax benefits of interest deductibility, debt permits owners of business or
investment assets to extract cash or to obtain a higher basis in the leveraged asset without an
additional equity investment.  A higher basis in a leveraged asset that is depreciable, for
example, can increase depreciation deductions.  This effect may in some situations create an
incentive for a business to borrow. 
In the event of financial difficulty, the discharge or restructuring of debt can cause the
issuer to recognize discharge of indebtedness income or alternatively, gain with respect to the
satisfaction of nonrecourse indebtedness for less than the outstanding amount. The income tax
treatment of debt discharge depends on whether the debt is recourse or nonrecourse, the nature of
the borrower’s assets and of the borrowing, and the circumstances of the restructuring or
discharge.  In a number of instances, no current income is recognized, though tax attributes such
as net operating losses, credits, or the basis of assets may be reduced.   By contrast, the failure to
pay dividends or return an equity investment in full does not cause income or gain to be
recognized by the issuer. 
In classifying an instrument as debt or equity, many factors have been applied by courts. 
In general, a debt instrument requires a fixed obligation to pay a certain amount at a specified
date.  Debt instruments provide for remedies including priorities in bankruptcy in the event of
default.  However, an instrument designated and respected as debt for tax purposes might  have
features that make it less likely to cause bankruptcy in the event of a downturn − for example, a
delayed period before payment is due, the ability to miss scheduled payments over a long period
of time before default occurs, the ability to satisfy required payments with instruments other than
cash, thin capitalization of the issuer, or ownership of the debt by equity owners who may be
willing to modify its terms rather than cause bankruptcy.   Conversely, an instrument designated
and respected as equity for tax purposes may have features that are more economically
burdensome to the issuer, such as significantly increased dividend payment requirements after a
specified period, puts and calls having the effect of requiring a cash redemption by a specified
date, or provisions giving the holders certain corporate governance rights in the event scheduled
payments are not made.  
Equity can be beneficial for tax purposes in certain cases.  Although corporate
distributions and sales of corporate stock subject the holder to tax in addition to any tax paid by
the corporation, reduced tax rates apply to holders with respect to such distributions or gain.
Dividends on corporate equity are largely excludable by corporate holders (currently resulting in
a maximum 10.5-percent tax rate under the 70-percent dividends received deduction).  For
individual shareholders, both dividends and capital gains on the sale of corporate stock are
generally subject to a maximum 15 percent rate (compared to the top individual rate of 35
percent).
4
  The present value of the shareholder-level tax on corporate earnings may be reduced
to the extent earnings are retained and to the extent shareholders do not sell their stock. This
second level of tax and may be eliminated entirely to the extent non-dividend-paying stock is
                                                
4
  The top individual rate on dividends of individuals is scheduled to increase to 39.6 percent after 2012, as
is the top rate on other individual ordinary income.  The top rate on long term capital gains of individuals is
scheduled to increase to 20 percent after 2012.   4
held until the death of the owner.  Receipt of equity also permits tax-free business combinations
and distributions, both in the case of corporations and partnerships.
The treatment of an instrument for purposes of financial reporting, for regulatory capital
purposes in a regulated industry (such as an insurance or banking), for ratings agency purposes,
and under foreign tax and nontax laws, may differ from it’s Federal income tax treatment.  
These differences may result in more favorable overall business treatment when the benefits of
debt or of equity for a Federal income tax purpose are combined with the benefits of a different
treatment for another purpose.    
   5
I. PRESENT LAW AND LEGISLATIVE BACKGROUND
A. General Rules
1. Issuer treatment of debt and equity 
Interest and dividend payments
Interest paid or accrued by a business is generally deductible, subject to a number of
limitations.
5
  By contrast, dividends or other returns to equity are not deductible. 
Timing of interest deduction
Interest generally is deducted as it is paid or accrues. However, interest can be deducted
in advance of actual payment or other accrual under the terms of the instrument when the amount
to be paid at the maturity of a debt instrument exceeds the issue price by more than a de minimis
amount. In such cases, a portion of the amount to be paid at maturity is treated as interest
accruing on a constant yield basis over the life of the instrument and is thus deducted in advance
of actual payment.
6
   Such interest is referred to as original issue discount (“OID”).        
Principal payments and return of equity capital
Principal payments on business debt are not generally deductible.
7
  The return of capital
to investors in an equity investment likewise is not deductible. 
Receipt of cash from debt or equity investors
The issuance of a debt or equity instrument for cash is not a taxable event to the issuer.  
Basis of assets purchased with debt or equity
Purchased assets generally have a cost basis for purposes of determining deprecation or
gain or loss on sale, regardless of whether the purchase was financed with debt (including
nonrecourse debt) or equity.  
Effect of entity level debt on partnership and S corporation equity holders
Equity investors in a partnership or an S corporation
8
 can deduct their allocable share of
partnership deductions (including depreciation, interest, or loss, for example.) only to the extent
                                                
5
  Sec. 163(a).  Some of these limitations are discussed below.
6
  Secs. 1273-1275. 
7
  There is an exception for certain debt incurred through a leveraged employee stock ownership plan
(“ESOP”). ESOPs are discussed at Part I.G.1.  6
the basis of their interest in the partnership or S corporation.
9
  A partner’s share of entity level
debt is included in the partner’s basis in his partnership interest.  An S corporation shareholder
does not include entity level debt in his S corporation stock basis.  However, the S corporation
shareholder may deduct losses to the extent of his basis in stock and his basis in debt that the
corporation owes to him.     
Nonpayments on equity compared to discharge or restructuring of indebtedness
If dividends are not paid on equity, or the capital contributed by an equity holder is not
returned, there is generally no taxable income, gain, or other consequence to the issuer.
10
 
The effects to the issuer if debt is modified, cancelled, or repurchased depend upon the
type of debt, the nature of the holder, and whether or not the debt (or property given in exchange
for it) is traded on an established securities market.  If debt is cancelled, modified, or
repurchased, the borrower generally realizes income from the discharge of indebtedness. 
Exceptions to this income inclusion are provided for bankruptcy and insolvency, for other
situations including seller financing of purchased property, qualified farm indebtedness, qualified
real property business indebtedness, and contributions of debt by an equity holder.  The
exceptions usually require the taxpayer to reduce the basis of property, or to reduce tax attributes
such as net operating losses.
11
  If nonrecourse debt is satisfied by foreclosure on the assets
securing the debt, the borrower generally realizes gain from the disposition of the assets for the
amount of the debt (even if the assets are not worth that amount).
12
  
Recourse indebtedness
If a taxpayer’s recourse debt is discharged, the taxpayer generally recognizes income
from the discharge of indebtedness at that time.
13
 A satisfaction of the debt with property worth
less than the debt,
14
 or a repurchase of debt for less than its face amount by the taxpayer or a
                                               
8
  An S corporation is a corporation that has only one class of stock, has no more than 100 shareholders
(after applying attribution rules), meets specific other requirements, and makes an election enabling its income and
deductions to pass through to its shareholders without entity level tax.  Sec. 1371 et seq.
9
  Other limitations on a partner’s or S corporation shareholder’s deductions also can apply, such as the
limitation on passive activity losses (sec. 469), or the at-risk limitation (sec. 465).
10
  Under certain circumstances an additional tax at the maximum individual rate on dividends (in addition
to the corporate income tax) applies to certain unreasonably accumulated income and to certain undistributed
income of a closely held corporation whose income is largely passive. Secs. 531-537 and secs. 541-547.  
11
  Sec. 108.  The rules relating to debt cancellation are discussed more fully at  Part III.B. 2.  
12
  Commissioner v. Tufts, 461 U.S. 300 (1983); cf., Crane v. Commissioner, 331 U.S. 1 (1947). 
13
  Sec. 108.
14
  For example, if a creditor contributes its debt to a corporation and receives corporate stock in exchange,
the corporation generally recognizes cancellation of indebtedness income to the extent the value of the stock given is
less than the amount of the debt cancelled. However, if the debt was held by a person that was also a shareholder, 7
related party, is treated as a discharge of the taxpayer’s debt to the extent of the difference
between the outstanding debt and (generally) the value of the property.
15
  
A significant modification of a debt instrument is treated as the disposition of the old
instrument in exchange for the new instrument.
16
  Such modifications include a change in the
obligor, a change in term or interest rate; a change in principal amount, and certain modifications
of security.  The modification of a debt instrument can thus cause the issuer to recognize
discharge of indebtedness income, measured by the difference between the adjusted issue price
of the old debt and the fair market value (or other applicable issue price) of the new debt.
17
   If
the debt instrument is publicly traded or is issued in exchange for property (including other debt)
that is publicly traded, then the issue price of the new debt is deemed to be the fair market value
of the debt or other property that is publicly traded.
18
  If neither the old nor the new debt
instrument is traded on an established securities market  the issue price of the new debt is
generally the stated principal amount unless there is inadequate stated interest (i.e., interest less
than the Treasury rate for an instrument of comparable term).
19
  Thus, in such traded situations,
discharge of indebtedness income is likely to be recognized if troubled debt is modified or
satisfied with other debt instruments. However, in private situations there may be no discharge of
indebtedness income.   
In  2008, special temporary rules were enacted allowing any taxpayer that experiences
discharge of indebtedness income arising from the reacquisition of its debt (including
modifications treated as a reacquisition) to defer including that income for a period of years and
then recognize the income ratably over a number of subsequent years. These rules applied to any
debt issued by a corporate taxpayer and to debt issued by any other taxpayer in connection with
the conduct of trade or business. They expired at the end of 2010.
20
   
                                               
the debt may be considered contributed in a nontaxable contribution to capital, not creating discharge of
indebtedness income. 
15
  Sec. 249.
16
  Treas. Reg. sec. 1.1001-3.
17
  The discharge of indebtedness income is taken into income at the time of the exchange.   The new debt
may be deemed to be issued with original issue discount (to the extent the amount payable at maturity exceeds the
issue price) that the issuer can deduct,  which can offset the amount of debt discharge income, but the deductions
occur in the future over the period of the new debt, while the income is recognized immediately. 
18
  Thus, if a distressed debt instrument is modified and the transaction is treated as an exchange of the old
instrument for the new one, the debtor can experience discharge of indebtedness income in the amount of the
difference between the adjusted issue price of the old debt and its fair market value at the time of the modification. 
19
  In certain “potentially abusive” cases, the principal amount of debt given in exchange for other property
(including other debt) is the fair market value of the property exchanged.  
20
  Pub. L. No.111-5, sec. 1231. Section 1232 gives the Treasury Department authority to suspend the
AHYDO rules or modify the rate for determining what is an AHYDO in certain distressed debt capital market
conditions.  8
Special rules allow a taxpayer not to recognize discharge of indebtedness income if the
taxpayer is in bankruptcy or is insolvent. These rules permit such taxpayers to reduce net
operating loss carryovers, depreciable asset basis, and other tax attributes that would provide tax
benefits in the future, in lieu of recognizing current income from the discharge of indebtedness. 
The rules differ depending on whether the issuer is insolvent or is in a bankruptcy or similar
proceeding. 
If the discharge of indebtedness occurs in a Title 11 bankruptcy case, the full amount of
any debt discharged is excluded from income.  If the taxpayer is insolvent, cancellation of debt
income is excludable only to the extent of the insolvency.  In either case, if the tax attributes
subject to reduction are insufficient to cover the amount of the discharge, there is no inclusion of
debt discharge income for the excess.  In the case of an entity that is taxed as a partnership, the
determinations whether the discharge occurs in a Title 11 bankruptcy case, whether the taxpayer
is insolvent, and the reduction of tax attributes, all occur at the partner level. 
Tax attributes are generally reduced in the following order: (1) net operating losses, (2)
general business credits, ( 3) minimum tax credits, (4) capital loss carryovers, (5) basis reduction
of property, (6) passive activity loss and credit carryovers, and (7) foreign tax credits.   A
taxpayer may elect to apply the reduction first against the basis of depreciable property.    
Other special rules allow a taxpayer that is not in bankruptcy or insolvent to exclude
discharge of indebtedness income and instead reduce the basis of certain real property.  These
rules apply only for discharge of certain qualified real estate indebtedness or qualified farm
indebtedness. The rules relating to qualified real estate indebtedness are available only to
noncorporate taxpayers.  
Purchase money financing
If debt that is discharged was seller-financing for a purchase of property by the debtor,
and if the debtor is not insolvent or in a bankruptcy proceeding, then instead of income from the
discharge of indebtedness, the debtor-purchaser has a purchase price reduction (which reduces
the basis of the property acquired).
Nonrecourse indebtedness
Nonrecourse debt is subject to different rules than recourse debt.
21
 Because the taxpayer
is not personally liable on the debt, there is no cancellation of indebtedness income. However, if
the creditor forecloses or otherwise takes the property securing the debt, the borrower treats the
transaction as a sale of the property for a price equal to the outstanding indebtedness (even if the
                                               
21
  The distinction between recourse and nonrecourse debt may be less obvious than it would appear. 
Recourse debt might be issued by an entity that has limited liability and limited assets, while nonrecourse debt might
be oversecured.  9
property securing the debt is worth less than the debt at the time of foreclosure).
22
  Such a
transaction generally produces capital gain (rather than ordinary income) to the debtor.  
2. Holder treatment of debt and equity 
Current income and sales of interests
Taxable investors
Interest on debt is taxed to a taxable individual or corporate holder at the ordinary income
tax rate of the holder (currently, up to 35 percent).
23
  Dividends paid by a taxable C
corporation,
24
  are generally taxed to a taxable individual shareholder at a maximum rate of 15
percent.
25
  Such dividends are generally taxed to a taxable C corporation shareholder at a
maximum rate of 10.5 percent (or less, depending on the percentage ownership the corporate
shareholder has in the issuing corporation).
26
  Gain on the sale of an equity interest in a C
corporation or in an S corporation is generally capital gain.  If the stock has been held for at least
one year, such gain is generally taxable to a taxable individual shareholder at a maximum rate of
15 percent.
27
 Gain on the sale of C corporation stock
28
  is taxed to a taxable corporate
shareholder
29
 at regular corporate rates (generally 35 percent).  Gain on the sale of an equity
                                               
22
  Commissioner v. Tufts, 461 U.S. 300 (1983); cf., Crane v. Commissioner, 331 U.S. 1 (1947).  
23
  The ordinary income rate for individuals is scheduled to increase to 39.6 percent after 2012.
24
  A C corporation is defined by reference to subchapter C of the Code  (tax rules relating to corporations
and shareholders) and is taxable as a separate entity with no deduction for dividends or other equity distributions. 
For purposes of the discussion in this document,, such corporations are distinguished from certain corporations that
meet specific tests relating to organization, functions, assets, and income types can deduct dividends and certain
other equity distributions to shareholders, (e.g., real estate investment trusts (REITs) or regulated investment
companies (RICs)).   A C corporation is also distinguished from an S corporation, governed by the additional rules
of subchapter S.  An S corporation is a corporation that has only one class of stock, has no more than 100
shareholders (after applying attribution rules), meets other specific requirements, and makes an election enabling its
income and deductions to pass through to its shareholders without entity level tax.  Sec. 1371 et seq.
25
  The maximum 15 percent rate on dividends of individuals is scheduled to increase to 39.6 percent after
2012.
26
  The lower rate on dividends received by a corporate shareholder results from the corporate “dividends
received deduction,” which is generally 70 percent of the dividend received if the shareholder owns below 20
percent of the issuer, 80 percent of the dividend received if the shareholder owns at least 20 percent and less than 80
percent of the issuer, and 100 percent of the dividend if the shareholder owns 80 percent of more of the issuer (sec.
243).  A corporation subject to the maximum 35 percent corporate tax rate and entitled to deduction 70 percent of a
dividend would pay a maximum tax on the dividend of 10.5 percent (the 30 percent of the dividend that is taxable,
multiplied by the 35 percent tax rate). 
27
  The maximum 15 percent rate on long-term capital gains of individuals is scheduled to increase to 20
percent after 2012.
28
  A corporate shareholder cannot own S corporation stock.   10
interest in a partnership is generally also capital gain of the partner, except for amounts
attributable to unrealized receivables and  inventory items of the partnership, which are taxable
as ordinary income.
30
  
Interest is generally taxable when paid or accrued. Interest generally is includable in
income, and thus taxable, before any cash payment if the original issue discount rules apply.  
Dividends are generally not taxable until paid.  However, in limited circumstances certain
preferred stock dividends may be accrued under rules similar to the rules for debt.  Also, a
shareholder may be treated as having received a dividend if his percentage stock ownership
increases as a result of the payment of dividends to other shareholders.
31
 
Tax-exempt investors
A tax-exempt investor (for example, a university endowment fund or a pension plan
investor) is generally not taxed on investment interest, subject to certain unrelated business
income tax (UBTI) rules for debt-financed income.
32
  This is true whether the debt is issued by a
C corporation or by any other entity.   
 Tax-exempt investors also are generally not subject to tax on sale of C corporation stock,
unless the stock investment is debt-financed.  
However, tax-exempt equity investors in a partnership are taxed as engaged in an
unrelated trade or business on their distributive share of partnership income from such a
business, as if they had conducted the business directly. And tax-exempt equity investors in an S
corporation (other than an ESOP investor) are taxed on their entire share of S corporation income
or gain on sale of the stock.
33
  
Foreign investors
Debt interests in U.S. entities
Although U.S.-source interest paid to a foreign investor is generally subject to a 30-
percent gross basis withholding tax, various exceptions exist in the Code and in bilateral income
                                               
29
  A C corporation is not an eligible S corporation shareholder and therefore cannot own S corporation
stock. 
30
  Sec. 751.
31
  Sec. 305(c).  Certain situations in which some shareholders receive cash and others experience an
increase in their percentage ownership can also cause both groups of shareholders to be treated as receiving a
dividend under that section. 
32
  Secs. 512, 514.
33
  Sec. 512(b). 11
tax treaties.
34
  Interest is generally derived from U.S. sources if it is paid by the United States or
any agency or instrumentality thereof, a State or any political subdivision thereof, or the District
of Columbia.  Interest is also from U.S. sources if it is paid by a noncorporate resident or a
domestic corporation on a bond, note, or other interest-bearing obligation.
35
  For this purpose, a
noncorporate resident includes a domestic partnership which at any time during the year was
engaged in a U.S. trade or business.
36
  Additionally, interest paid by the U.S. branch of a foreign
corporation is also treated as U.S.-source income.
37
Statutory exceptions to this general rule apply for interest on bank deposits as well as
portfolio interest.  Interest on bank deposits may qualify for exemption on two grounds,
depending on where the underlying principal is held on deposit.  Interest paid with respect to
deposits with domestic banks and savings and loan associations, and certain amounts held by
insurance companies, are U.S.-source income but are not subject to the U.S. withholding tax
when paid to a foreign person, unless the interest is effectively connected with a U.S. trade or
business of the recipient.
38
  Interest on deposits with foreign branches of domestic banks and
domestic savings and loan associations is not treated as U.S.-source income and is thus exempt
from U.S. withholding tax (regardless of whether the recipient is a U.S. or foreign person).
39
 
Similarly, interest and original issue discount on certain short-term obligations is also exempt
from U.S. withholding tax when paid to a foreign person.
40
  
Portfolio interest received by a nonresident individual or foreign corporation from
sources within the United States is exempt from U.S. withholding tax.
41
  For obligations issued
before March 19, 2012, the term “portfolio interest” means any interest (including original issue
                                               
34
  Where a foreign investor is engaged in a U.S. trade or business, any U.S. source interest income or U.S.
source dividend income (see “Equity interest in U.S. Entities” below) derived from assets used in or held for use in
the conduct of the U.S. trade or business where the activities of the trade or business were material factor in the
realization of such income will be treated as effectively connected with that U.S. trade or business.  Sec. 864(a)(2).  
35
  Sec. 861(a)(1); Treas. Reg. sec. 1.861-2(a)(1).  However, special rules apply to treat as foreign source
certain amounts paid on deposits with foreign commercial banking branches of U.S. corporations or partnerships and
certain other amounts paid by foreign branches of domestic financial institutions.  Sec. 861(a)(1).  Prior to January
1, 2011, all (or a portion) of a payment of interest by a resident alien individual or domestic corporation was treated
as foreign source if such individual or corporation met an 80-percent foreign business requirement.  This provision
was generally repealed for tax years beginning after December 31, 2010.  
36
  Treas. Reg. sec. 1.861-2(a)(2).
37
  Sec. 884(f)(1).
38
  Secs. 871(i)(2)(A), 881(d); Treas. Reg. sec. 1.1441-1(b)(4)(ii).  
39
  Sec. 861(a)(1)(B); Treas. Reg. sec. 1.1441-1(b)(4)(iii).  
40
  Secs. 871(g)(1)(B), 881(a)(3); Treas. Reg. sec. 1.1441-1(b)(4)(iv).
41
  Secs. 871(h), 881(c).  In 1984, to facilitate access to the global market for U.S. dollar-denominated debt
obligations, Congress repealed the withholding tax on portfolio interest paid on debt obligations issued by U.S.
persons.  See Joint Committee on Taxation, General Explanation of the Revenue Provisions of the Deficit Reduction
Act of 1984 (JCS-41-84), December 31, 1984, pp. 391-92. 12
discount) that is paid on an obligation that is in registered form and for which the beneficial
owner has provided to the U.S. withholding agent a statement certifying that the beneficial owner
is not a U.S. person, as well as interest paid on an obligation that is not in registered form and
that meets the foreign targeting requirements of section 163(f)(2)(B).  Portfolio interest,
however, does not include interest received by a 10-percent shareholder,
42
 certain contingent
interest,
43
 interest received by a controlled foreign corporation from a related person,
44
 or interest
received by a bank on an extension of credit made pursuant to a loan agreement entered into in
the ordinary course of its trade or business.
45
For obligations issued after March 18, 2012, the term “portfolio interest” no longer
includes interest paid with respect to an obligation not in registered form. This narrowing of the
scope of the portfolio interest exemption is a result of the repeal of the exception to the
registration requirements for foreign targeted securities in 2010, effective for obligations issued
two years after enactment.
46
 
U.S.-source interest payments that do not qualify for a statutory exemption from the 30-
percent withholding tax often are exempt from withholding under U.S. bilateral income tax
treaties.  Many treaties, including, for example, those with Canada, Germany, and the United
Kingdom, broadly eliminate the withholding tax on U.S.-source interest payments.  The result is
that large volumes of interest payments are exempt from withholding under the Code or a treaty.
Equity interests in U.S. entities
A foreign equity investor’s receipt of U.S.-source dividend income from a U.S. domestic
corporation is generally subject to a 30-percent gross basis withholding tax.  Dividend income is
generally sourced by reference to the payor’s place of incorporation such that dividends paid by
a domestic corporation are generally treated as entirely U.S.-source income.
 47
  As with interest,
the 30-percent withholding tax on dividends received by foreign investors may be reduced or
eliminated under U.S. bilateral income tax treaties.  In general, the dividend withholding tax
rates in treaties vary based on the percentage of stock of the dividend-paying company owned by
the recipient of the dividend.  Treaties typically provide lower withholding tax rates (five
percent, for example) at ownership levels of ten percent and greater.  Twelve treaties, including
those with Germany, Japan, and the United Kingdom, eliminate the withholding tax on dividends
in circumstances in which, among other requirements, the foreign treaty resident is a company
that owns at least 80 percent (in the case of Japan, 50 percent) of the U.S. corporation paying the
dividend.
                                               
42JCT examines tax treatment of business debt

JCX-41-11, Present Law And Background Relating To Tax Treatment Of Business Debt


Due to growing concern about the level of corporate debt (along with household and Federal debt), the Joint Committee on Taxation (JCT) has released a report on the Federal tax rules on the use of debt leverage by businesses in the U.S. From '87 to 2010, corporate debt, as a percentage of gross national product (GNP), has risen from 42.8% to 48.3%, a significant increase (although less dramatic than the 57.9% to 90.2% increase in household debt and the 41% to 63.2% increase in Federal debt).

Background on issuer treatment of debt and equity. In general, interest paid or accrued by a business is deductible under Code Sec. 163(a) , subject to a number of limitations. Interest generally is deducted as it is paid or accrues. But, original issue discount (OID) interest (where the amount to be paid at the maturity of a debt instrument exceeds the issue price by more than a de minimis amount) is deducted in advance of actual payment or other accrual under the terms of the instrument. ( Code Sec. 163(e) )

Dividends or other returns on equity aren't deductible. The issuance of a debt or equity instrument for cash is not a taxable event to the issuer. Purchased assets generally have a cost basis for purposes of determining deprecation or gain or loss on sale, regardless of whether the purchase was financed with debt (including nonrecourse debt) or equity. If dividends are not paid on equity, or the capital contributed by an equity holder isn't returned, there is generally no taxable income, gain, or other consequence to the issuer.

If debt is cancelled, modified, or repurchased, the borrower generally realizes income from the discharge of indebtedness. Exceptions to this income inclusion are provided for bankruptcy and insolvency, other situations including seller financing of purchased property, qualified farm indebtedness, qualified real property business indebtedness, and contributions of debt by an equity holder. The exceptions usually require the taxpayer to reduce the basis of property, or to reduce tax attributes such as net operating losses. A significant modification of a debt instrument is treated as the disposition of the old instrument in exchange for the new instrument.

If nonrecourse debt is satisfied by foreclosure on the assets securing the debt, the borrower generally realizes gain from the disposition of the assets for the amount of the debt (even if the assets are not worth that amount).

Background on holder treatment of debt and equity. Interest on debt is taxed to a taxable individual or corporate holder at the ordinary income tax rate of the holder (currently, up to 35%). Dividends paid by a taxable C corporation are generally taxed to an individual shareholder at a maximum rate of 15%. Dividends are generally taxed to a C corporation shareholder at a maximum rate of 10.5% (or less, depending on the percentage ownership the corporate shareholder has in the issuing corporation). Gain on the sale of an equity interest in a C corporation or in an S corporation is generally capital gain. If the stock has been held for at least one year, such gain is generally taxable to an individual shareholder at a maximum rate of 15%. Gain on the sale of C corporation stock is taxed to a corporate shareholder at regular corporate rates (generally 35%). Gain on the sale of an equity interest in a partnership is also generally capital gain of the partner, except for amounts attributable to unrealized receivables and inventory items of the partnership, which are taxable as ordinary income. Interest is generally taxable when paid or accrued.

Interest is generally includable in income and taxable before any cash payment if the OID rules apply. Dividends are generally not taxable until paid. However, in limited circumstances, certain preferred stock dividends may be accrued under rules similar to the rules for debt. A shareholder may also be treated as having received a dividend if his percentage of stock ownership increases as a result of the payment of dividends to other shareholders.

A tax-exempt investor is generally not taxed on investment interest, subject to certain unrelated business income tax rules for debt-financed income. Although U.S.-source interest paid to a foreign investor is generally subject to a 30% withholding tax, various exceptions exist in the Code and in Treaties.

JCT's analysis. The JCT Report concludes that the Federal income tax treatment of debt and equity creates incentives to utilize one or the other depending on the tax characteristics of the issuer and of the particular investor. Taxpayers have considerable flexibility to design instruments treated as either debt or equity but which blend features traditionally associated with both. In general, a corporate issuer isn't subject to corporate tax on amounts that it deducts as interest on debt. On the other hand, dividends, which aren't deductible by the payor, come out of the corporation's after-tax income.

Debt instruments can allow the accrual of the interest deduction along with the inclusion in income by the holder at a time before the payment of cash. Interest income may be taxed at a higher rate to a taxable holder than the holder's dividends or capital gains attributable to corporate retained earnings (to which lower tax rates currently apply). While some forms of debt investments aren't subject to U.S. tax or are taxed at reduced rates in the hands of a tax-exempt or foreign investor—resulting in tax arbitrage that can shelter otherwise taxable income—special rules in the Code apply in these situations to limit interest deductions.

In some situations, business may have an incentive to borrow. Debt allows owners of business or investment assets to extract cash or obtain a higher basis in the leveraged asset without an additional equity investment. For example, a higher basis in a leveraged asset that is depreciable can increase depreciation deductions.

The discharge or restructuring of debt in the event of financial difficulty can cause the issuer to recognize discharge of indebtedness income or gain with respect to the satisfaction of nonrecourse indebtedness for less than the outstanding amount. The income tax treatment of debt discharge depends on whether the debt is recourse or nonrecourse, the nature of the borrower's assets and of the borrowing, and the circumstances of the restructuring or discharge. In a number of instances, no current income is recognized, though tax attributes such as net operating losses, credits, or the basis of assets may be reduced. On the other hand, the failure to pay dividends or return an equity investment in full doesn't cause income or gain to be recognized by the issuer.

The tax law generally contains no fixed definition of debt or equity. In classifying an instrument as debt or equity, the courts have applied many factors. In general, a debt instrument requires a fixed obligation to pay a certain amount at a specified date. Debt instruments provide for remedies including priorities in bankruptcy in the event of default. Conversely, an instrument designated and respected as equity for tax purposes may have features that are more economically burdensome to the issuer.

Equity can be beneficial for tax purposes in certain cases. Although corporate distributions and sales of corporate stock subject the holder to tax in addition to any tax paid by the corporation, reduced tax rates apply to holders with respect to such distributions or gain. Dividends on corporate equity are largely excludable by corporate holders (currently resulting in a maximum 10.5% tax rate under the 70% dividends received deduction). For individual shareholders, both dividends and capital gains on the sale of corporate stock are generally subject to a maximum 15% rate (compared to the top individual rate of 35%).

Different treatment of an instrument for purposes of financial reporting, for regulatory capital purposes in a regulated industry (such as an insurance or banking), for ratings agency purposes, and under foreign tax and nontax laws, may result in more favorable overall business treatment when combined with the benefits of debt or equity for Federal income tax purposes.















PRESENT LAW AND BACKGROUND RELATING
TO TAX TREATMENT OF BUSINESS DEBT
A REPORT TO THE
JOINT COMMITTEE ON TAXATION
Prepared by the Staff
of the
JOINT COMMITTEE ON TAXATION
July 11, 2011
JCX-41-11 i
CONTENTS
Page
INTRODUCTION AND SUMMARY ........................................................................................... 1
I. PRESENT LAW AND LEGISLATIVE BACKGROUND ........................................................ 5
A. General Rules ...................................................................................................................... 5
1. Issuer treatment of debt and equity ............................................................................... 5
2. Holder treatment of debt and equity ............................................................................. 9
3. Acquisitions and dispositions ..................................................................................... 13
B. Definition of Debt and Equity ........................................................................................... 15
1. Distinguishing debt from equity ................................................................................. 15
2. Regulatory authority pursuant to section 385 ............................................................. 17
C. Rules to Address Stripping of U.S. Corporate Tax Base in the Case of Nontaxed
Holders .............................................................................................................................. 20
1. Earnings stripping ....................................................................................................... 20
2. Tax treatment of certain payments to controlling exempt organizations .................... 23
D. Rules to Address Corporate Base Erosion Without Regard to Holders’ Tax Status ........ 25
1. Corporate Equity Reduction Transactions .................................................................. 25
2. Debt expected to be paid in equity .............................................................................. 27
3. Applicable high-yield discount obligations ................................................................ 28
4. Interest on certain acquisition indebtedness ............................................................... 30
E. Rules to Address Tax Arbitrage in the Case of Borrowing to Fund Untaxed Income ..... 31
1. Interest related to tax-exempt income ......................................................................... 31
2. Debt with respect to certain insurance products ......................................................... 35
3. Debt-financed income of tax-exempt organizations ................................................... 39
4. Dividends received deduction reduction for debt-financed portfolio stock ................ 41
F. Rules to Match Timing of Tax Deduction and Income Inclusion Relating to Debt ......... 43
1. Interest and OID on amounts payable to related foreign lenders ................................ 43
2. Construction period interest ........................................................................................ 45
3. Interest in the case of straddles ................................................................................... 46
G. Other Rules Relating to Business Debt and Equity .......................................................... 48
1. Employee Stock Ownership Plans .............................................................................. 48
2. Nonqualified preferred stock not treated as stock for certain purposes ...................... 52
II. DATA WITH RESPECT TO BUSINESS DEBT .................................................................. 56
III. ECONOMIC INCENTIVES CREATED UNDER PRESENT LAW FOR BUSINESS
DEBT ...................................................................................................................................... 64
A. Incentives Related to Firm Capital Structure .................................................................... 64
1. Tax incentives for debt ................................................................................................ 67
2. Tax incentives related to equity .................................................................................. 78
3. Incentives to create hybrid instruments ...................................................................... 80
4. Incentives to substitute other arrangements for debt .................................................. 85ii
5. Incentives to use leveraged ESOPs ............................................................................. 86
6. Financial accounting and other considerations ........................................................... 90
IV. TAX TREATMENT OF CORPORATE DEBT IN SELECTED COUNTRIES ................... 95
A. Summary ........................................................................................................................... 95
B. Law Library of Congress: Tax Treatment of Corporate Debt .......................................... 971
INTRODUCTION AND SUMMARY
Introduction
This document
1
 has been prepared by the staff of the Joint Committee on Taxation, in
response to the request of the Chairman and Vice Chairman of the Joint Committee on Taxation
for a report of Federal tax rules relating to the use of leverage by households and businesses in
the United States.
2
  
There has been concern about the level of debt in the U.S. economy.  Below is a table
illustrating corporate debt, household debt, and Federal debt as a percentage of gross national
product (GNP), 1987-2010.  This document relates to business debt; corporate data is shown in
column one of Table 1, below.
Table 1.−Corporate Debt, Household Debt, and Federal Debt, as a Percentage
of Gross National Product (GNP), 1987-2010
Year
Corporate Debt
1
as a Percentage of
GNP
Household Debt
2
as a Percentage of
GNP
Federal Debt
3
as a Percentage of
GNP
1987 42.8 57.9 41.0
1990 43.6 61.4 42.8
1995 39.5 65.0 48.9
2000 46.4 69.9 33.9
2005 43.0 92.4 36.9
2010 48.3 90.2 63.2
1
  Corporate debt of nonfinancial C corporations and S corporations excluding farms.
2
  Household debt includes debt of personal trusts, nonprofit organizations, partnerships and sole
proprietorships.
3
  Federal debt excludes federal debt held by Federal agency trust funds.
Sources:  Debt levels from The Board of Governors of the Federal Reserve System Flow of Funds Accounts
of the United States:  Flows and Outstandings First Quarter 2011 Table D.3. GNP levels from the Federal
Reserve Bank of St. Louis. 
The first part of this document presents an overview of Federal income tax rules relating
to debt and equity, and some of the statutory limitations on the benefits of each.  The overview
includes the treatment of issuers as well as holders, and the treatment of each in the event of a
business downturn in which the instrument becomes worthless.  
                                                
1
  This document may be cited as follows:  Joint Committee on Taxation, Present Law and Background
Relating to Tax Treatment of Business Debt (JCX-41-11), July 11, 2011.  This document can be found on our
website at www.jct.gov.   
2
  The request was made at the 112
th
 Congress Organizational Meeting of the Joint Committee on Taxation
on March 15, 2011. 2
The second part of this document presents data regarding nonfinancial business sector
debt and other business debt over several decades.  
The third part of this document describes incentives for debt or equity that exist in the
absence of tax considerations, a discussion of the incentives that may be created by the presentlaw tax treatment of instruments as debt or as equity.   
A companion document
3
 provides economic data with respect to household debt and
provides a description of Federal tax rules governing household debt and economic incentives
under present law.
Summary
Business enterprises and their investors have business reasons to structure capital
investment as either debt or equity.  For example, investors may prefer varying levels of risk. 
Investors may seek different levels of priority in the event of bankruptcy of the business. 
Businesses can issue interests to investors that have varying levels of control over the enterprise
and degrees of participation in profitability or growth of the enterprise. 
The tax law generally contains no fixed definition of debt or equity.  Taxpayers have
considerable flexibility to design instruments treated as either debt or equity but which blend
features traditionally associated with both.    
The Federal income tax treatment of debt and of equity creates incentives to utilize one or
the other depending on the tax characteristics of the issuer and of the particular investor.  In
general, a corporate issuer is not subject to corporate tax on amounts that it deducts as interest on
debt.  By contrast, dividends, which are not deductible by the payor, come out of after-tax
income of the corporation.  
Debt instruments can permit the accrual of the interest deduction along with the inclusion
in income by the holder at a time prior to the payment of cash.  Interest income may be taxed at a
higher rate to a taxable holder than the holder’s dividends or capital gains attributable to
corporate retained earnings (to which lower tax rates currently apply).  However, some forms of
debt investments are not subject to U.S. tax or are taxed at reduced rates in the hands of a taxexempt or foreign investor. A number of special rules in the Code are designed to limit the tax
benefits that can be obtained from interest deductions to protect the corporate tax base. 
To the extent that debt finances assets that produce tax-exempt or otherwise tax-favored
income, the interest deduction is available to offset other income taxed at higher rates.  The
resulting tax arbitrage can shelter otherwise taxable income. A number of special rules in the
Code are directed at limiting this effect. 
                                               
3
  Joint Committee on Taxation, Present Law and Background Relating to Tax Treatment of Household
Debt (JCX-40-11), July 11, 2011 (hereinafter “Tax Treatment of Household Debt”).  This document can be found on
our website at www.jct.gov.  3
In addition to the tax benefits of interest deductibility, debt permits owners of business or
investment assets to extract cash or to obtain a higher basis in the leveraged asset without an
additional equity investment.  A higher basis in a leveraged asset that is depreciable, for
example, can increase depreciation deductions.  This effect may in some situations create an
incentive for a business to borrow. 
In the event of financial difficulty, the discharge or restructuring of debt can cause the
issuer to recognize discharge of indebtedness income or alternatively, gain with respect to the
satisfaction of nonrecourse indebtedness for less than the outstanding amount. The income tax
treatment of debt discharge depends on whether the debt is recourse or nonrecourse, the nature of
the borrower’s assets and of the borrowing, and the circumstances of the restructuring or
discharge.  In a number of instances, no current income is recognized, though tax attributes such
as net operating losses, credits, or the basis of assets may be reduced.   By contrast, the failure to
pay dividends or return an equity investment in full does not cause income or gain to be
recognized by the issuer. 
In classifying an instrument as debt or equity, many factors have been applied by courts. 
In general, a debt instrument requires a fixed obligation to pay a certain amount at a specified
date.  Debt instruments provide for remedies including priorities in bankruptcy in the event of
default.  However, an instrument designated and respected as debt for tax purposes might  have
features that make it less likely to cause bankruptcy in the event of a downturn − for example, a
delayed period before payment is due, the ability to miss scheduled payments over a long period
of time before default occurs, the ability to satisfy required payments with instruments other than
cash, thin capitalization of the issuer, or ownership of the debt by equity owners who may be
willing to modify its terms rather than cause bankruptcy.   Conversely, an instrument designated
and respected as equity for tax purposes may have features that are more economically
burdensome to the issuer, such as significantly increased dividend payment requirements after a
specified period, puts and calls having the effect of requiring a cash redemption by a specified
date, or provisions giving the holders certain corporate governance rights in the event scheduled
payments are not made.  
Equity can be beneficial for tax purposes in certain cases.  Although corporate
distributions and sales of corporate stock subject the holder to tax in addition to any tax paid by
the corporation, reduced tax rates apply to holders with respect to such distributions or gain.
Dividends on corporate equity are largely excludable by corporate holders (currently resulting in
a maximum 10.5-percent tax rate under the 70-percent dividends received deduction).  For
individual shareholders, both dividends and capital gains on the sale of corporate stock are
generally subject to a maximum 15 percent rate (compared to the top individual rate of 35
percent).
4
  The present value of the shareholder-level tax on corporate earnings may be reduced
to the extent earnings are retained and to the extent shareholders do not sell their stock. This
second level of tax and may be eliminated entirely to the extent non-dividend-paying stock is
                                                
4
  The top individual rate on dividends of individuals is scheduled to increase to 39.6 percent after 2012, as
is the top rate on other individual ordinary income.  The top rate on long term capital gains of individuals is
scheduled to increase to 20 percent after 2012.   4
held until the death of the owner.  Receipt of equity also permits tax-free business combinations
and distributions, both in the case of corporations and partnerships.
The treatment of an instrument for purposes of financial reporting, for regulatory capital
purposes in a regulated industry (such as an insurance or banking), for ratings agency purposes,
and under foreign tax and nontax laws, may differ from it’s Federal income tax treatment.  
These differences may result in more favorable overall business treatment when the benefits of
debt or of equity for a Federal income tax purpose are combined with the benefits of a different
treatment for another purpose.    
   5
I. PRESENT LAW AND LEGISLATIVE BACKGROUND
A. General Rules
1. Issuer treatment of debt and equity 
Interest and dividend payments
Interest paid or accrued by a business is generally deductible, subject to a number of
limitations.
5
  By contrast, dividends or other returns to equity are not deductible. 
Timing of interest deduction
Interest generally is deducted as it is paid or accrues. However, interest can be deducted
in advance of actual payment or other accrual under the terms of the instrument when the amount
to be paid at the maturity of a debt instrument exceeds the issue price by more than a de minimis
amount. In such cases, a portion of the amount to be paid at maturity is treated as interest
accruing on a constant yield basis over the life of the instrument and is thus deducted in advance
of actual payment.
6
   Such interest is referred to as original issue discount (“OID”).        
Principal payments and return of equity capital
Principal payments on business debt are not generally deductible.
7
  The return of capital
to investors in an equity investment likewise is not deductible. 
Receipt of cash from debt or equity investors
The issuance of a debt or equity instrument for cash is not a taxable event to the issuer.  
Basis of assets purchased with debt or equity
Purchased assets generally have a cost basis for purposes of determining deprecation or
gain or loss on sale, regardless of whether the purchase was financed with debt (including
nonrecourse debt) or equity.  
Effect of entity level debt on partnership and S corporation equity holders
Equity investors in a partnership or an S corporation
8
 can deduct their allocable share of
partnership deductions (including depreciation, interest, or loss, for example.) only to the extent
                                                
5
  Sec. 163(a).  Some of these limitations are discussed below.
6
  Secs. 1273-1275. 
7
  There is an exception for certain debt incurred through a leveraged employee stock ownership plan
(“ESOP”). ESOPs are discussed at Part I.G.1.  6
the basis of their interest in the partnership or S corporation.
9
  A partner’s share of entity level
debt is included in the partner’s basis in his partnership interest.  An S corporation shareholder
does not include entity level debt in his S corporation stock basis.  However, the S corporation
shareholder may deduct losses to the extent of his basis in stock and his basis in debt that the
corporation owes to him.     
Nonpayments on equity compared to discharge or restructuring of indebtedness
If dividends are not paid on equity, or the capital contributed by an equity holder is not
returned, there is generally no taxable income, gain, or other consequence to the issuer.
10
 
The effects to the issuer if debt is modified, cancelled, or repurchased depend upon the
type of debt, the nature of the holder, and whether or not the debt (or property given in exchange
for it) is traded on an established securities market.  If debt is cancelled, modified, or
repurchased, the borrower generally realizes income from the discharge of indebtedness. 
Exceptions to this income inclusion are provided for bankruptcy and insolvency, for other
situations including seller financing of purchased property, qualified farm indebtedness, qualified
real property business indebtedness, and contributions of debt by an equity holder.  The
exceptions usually require the taxpayer to reduce the basis of property, or to reduce tax attributes
such as net operating losses.
11
  If nonrecourse debt is satisfied by foreclosure on the assets
securing the debt, the borrower generally realizes gain from the disposition of the assets for the
amount of the debt (even if the assets are not worth that amount).
12
  
Recourse indebtedness
If a taxpayer’s recourse debt is discharged, the taxpayer generally recognizes income
from the discharge of indebtedness at that time.
13
 A satisfaction of the debt with property worth
less than the debt,
14
 or a repurchase of debt for less than its face amount by the taxpayer or a
                                               
8
  An S corporation is a corporation that has only one class of stock, has no more than 100 shareholders
(after applying attribution rules), meets specific other requirements, and makes an election enabling its income and
deductions to pass through to its shareholders without entity level tax.  Sec. 1371 et seq.
9
  Other limitations on a partner’s or S corporation shareholder’s deductions also can apply, such as the
limitation on passive activity losses (sec. 469), or the at-risk limitation (sec. 465).
10
  Under certain circumstances an additional tax at the maximum individual rate on dividends (in addition
to the corporate income tax) applies to certain unreasonably accumulated income and to certain undistributed
income of a closely held corporation whose income is largely passive. Secs. 531-537 and secs. 541-547.  
11
  Sec. 108.  The rules relating to debt cancellation are discussed more fully at  Part III.B. 2.  
12
  Commissioner v. Tufts, 461 U.S. 300 (1983); cf., Crane v. Commissioner, 331 U.S. 1 (1947). 
13
  Sec. 108.
14
  For example, if a creditor contributes its debt to a corporation and receives corporate stock in exchange,
the corporation generally recognizes cancellation of indebtedness income to the extent the value of the stock given is
less than the amount of the debt cancelled. However, if the debt was held by a person that was also a shareholder, 7
related party, is treated as a discharge of the taxpayer’s debt to the extent of the difference
between the outstanding debt and (generally) the value of the property.
15
  
A significant modification of a debt instrument is treated as the disposition of the old
instrument in exchange for the new instrument.
16
  Such modifications include a change in the
obligor, a change in term or interest rate; a change in principal amount, and certain modifications
of security.  The modification of a debt instrument can thus cause the issuer to recognize
discharge of indebtedness income, measured by the difference between the adjusted issue price
of the old debt and the fair market value (or other applicable issue price) of the new debt.
17
   If
the debt instrument is publicly traded or is issued in exchange for property (including other debt)
that is publicly traded, then the issue price of the new debt is deemed to be the fair market value
of the debt or other property that is publicly traded.
18
  If neither the old nor the new debt
instrument is traded on an established securities market  the issue price of the new debt is
generally the stated principal amount unless there is inadequate stated interest (i.e., interest less
than the Treasury rate for an instrument of comparable term).
19
  Thus, in such traded situations,
discharge of indebtedness income is likely to be recognized if troubled debt is modified or
satisfied with other debt instruments. However, in private situations there may be no discharge of
indebtedness income.   
In  2008, special temporary rules were enacted allowing any taxpayer that experiences
discharge of indebtedness income arising from the reacquisition of its debt (including
modifications treated as a reacquisition) to defer including that income for a period of years and
then recognize the income ratably over a number of subsequent years. These rules applied to any
debt issued by a corporate taxpayer and to debt issued by any other taxpayer in connection with
the conduct of trade or business. They expired at the end of 2010.
20
   
                                               
the debt may be considered contributed in a nontaxable contribution to capital, not creating discharge of
indebtedness income. 
15
  Sec. 249.
16
  Treas. Reg. sec. 1.1001-3.
17
  The discharge of indebtedness income is taken into income at the time of the exchange.   The new debt
may be deemed to be issued with original issue discount (to the extent the amount payable at maturity exceeds the
issue price) that the issuer can deduct,  which can offset the amount of debt discharge income, but the deductions
occur in the future over the period of the new debt, while the income is recognized immediately. 
18
  Thus, if a distressed debt instrument is modified and the transaction is treated as an exchange of the old
instrument for the new one, the debtor can experience discharge of indebtedness income in the amount of the
difference between the adjusted issue price of the old debt and its fair market value at the time of the modification. 
19
  In certain “potentially abusive” cases, the principal amount of debt given in exchange for other property
(including other debt) is the fair market value of the property exchanged.  
20
  Pub. L. No.111-5, sec. 1231. Section 1232 gives the Treasury Department authority to suspend the
AHYDO rules or modify the rate for determining what is an AHYDO in certain distressed debt capital market
conditions.  8
Special rules allow a taxpayer not to recognize discharge of indebtedness income if the
taxpayer is in bankruptcy or is insolvent. These rules permit such taxpayers to reduce net
operating loss carryovers, depreciable asset basis, and other tax attributes that would provide tax
benefits in the future, in lieu of recognizing current income from the discharge of indebtedness. 
The rules differ depending on whether the issuer is insolvent or is in a bankruptcy or similar
proceeding. 
If the discharge of indebtedness occurs in a Title 11 bankruptcy case, the full amount of
any debt discharged is excluded from income.  If the taxpayer is insolvent, cancellation of debt
income is excludable only to the extent of the insolvency.  In either case, if the tax attributes
subject to reduction are insufficient to cover the amount of the discharge, there is no inclusion of
debt discharge income for the excess.  In the case of an entity that is taxed as a partnership, the
determinations whether the discharge occurs in a Title 11 bankruptcy case, whether the taxpayer
is insolvent, and the reduction of tax attributes, all occur at the partner level. 
Tax attributes are generally reduced in the following order: (1) net operating losses, (2)
general business credits, ( 3) minimum tax credits, (4) capital loss carryovers, (5) basis reduction
of property, (6) passive activity loss and credit carryovers, and (7) foreign tax credits.   A
taxpayer may elect to apply the reduction first against the basis of depreciable property.    
Other special rules allow a taxpayer that is not in bankruptcy or insolvent to exclude
discharge of indebtedness income and instead reduce the basis of certain real property.  These
rules apply only for discharge of certain qualified real estate indebtedness or qualified farm
indebtedness. The rules relating to qualified real estate indebtedness are available only to
noncorporate taxpayers.  
Purchase money financing
If debt that is discharged was seller-financing for a purchase of property by the debtor,
and if the debtor is not insolvent or in a bankruptcy proceeding, then instead of income from the
discharge of indebtedness, the debtor-purchaser has a purchase price reduction (which reduces
the basis of the property acquired).
Nonrecourse indebtedness
Nonrecourse debt is subject to different rules than recourse debt.
21
 Because the taxpayer
is not personally liable on the debt, there is no cancellation of indebtedness income. However, if
the creditor forecloses or otherwise takes the property securing the debt, the borrower treats the
transaction as a sale of the property for a price equal to the outstanding indebtedness (even if the
                                               
21
  The distinction between recourse and nonrecourse debt may be less obvious than it would appear. 
Recourse debt might be issued by an entity that has limited liability and limited assets, while nonrecourse debt might
be oversecured.  9
property securing the debt is worth less than the debt at the time of foreclosure).
22
  Such a
transaction generally produces capital gain (rather than ordinary income) to the debtor.  
2. Holder treatment of debt and equity 
Current income and sales of interests
Taxable investors
Interest on debt is taxed to a taxable individual or corporate holder at the ordinary income
tax rate of the holder (currently, up to 35 percent).
23
  Dividends paid by a taxable C
corporation,
24
  are generally taxed to a taxable individual shareholder at a maximum rate of 15
percent.
25
  Such dividends are generally taxed to a taxable C corporation shareholder at a
maximum rate of 10.5 percent (or less, depending on the percentage ownership the corporate
shareholder has in the issuing corporation).
26
  Gain on the sale of an equity interest in a C
corporation or in an S corporation is generally capital gain.  If the stock has been held for at least
one year, such gain is generally taxable to a taxable individual shareholder at a maximum rate of
15 percent.
27
 Gain on the sale of C corporation stock
28
  is taxed to a taxable corporate
shareholder
29
 at regular corporate rates (generally 35 percent).  Gain on the sale of an equity
                                               
22
  Commissioner v. Tufts, 461 U.S. 300 (1983); cf., Crane v. Commissioner, 331 U.S. 1 (1947).  
23
  The ordinary income rate for individuals is scheduled to increase to 39.6 percent after 2012.
24
  A C corporation is defined by reference to subchapter C of the Code  (tax rules relating to corporations
and shareholders) and is taxable as a separate entity with no deduction for dividends or other equity distributions. 
For purposes of the discussion in this document,, such corporations are distinguished from certain corporations that
meet specific tests relating to organization, functions, assets, and income types can deduct dividends and certain
other equity distributions to shareholders, (e.g., real estate investment trusts (REITs) or regulated investment
companies (RICs)).   A C corporation is also distinguished from an S corporation, governed by the additional rules
of subchapter S.  An S corporation is a corporation that has only one class of stock, has no more than 100
shareholders (after applying attribution rules), meets other specific requirements, and makes an election enabling its
income and deductions to pass through to its shareholders without entity level tax.  Sec. 1371 et seq.
25
  The maximum 15 percent rate on dividends of individuals is scheduled to increase to 39.6 percent after
2012.
26
  The lower rate on dividends received by a corporate shareholder results from the corporate “dividends
received deduction,” which is generally 70 percent of the dividend received if the shareholder owns below 20
percent of the issuer, 80 percent of the dividend received if the shareholder owns at least 20 percent and less than 80
percent of the issuer, and 100 percent of the dividend if the shareholder owns 80 percent of more of the issuer (sec.
243).  A corporation subject to the maximum 35 percent corporate tax rate and entitled to deduction 70 percent of a
dividend would pay a maximum tax on the dividend of 10.5 percent (the 30 percent of the dividend that is taxable,
multiplied by the 35 percent tax rate). 
27
  The maximum 15 percent rate on long-term capital gains of individuals is scheduled to increase to 20
percent after 2012.
28
  A corporate shareholder cannot own S corporation stock.   10
interest in a partnership is generally also capital gain of the partner, except for amounts
attributable to unrealized receivables and  inventory items of the partnership, which are taxable
as ordinary income.
30
  
Interest is generally taxable when paid or accrued. Interest generally is includable in
income, and thus taxable, before any cash payment if the original issue discount rules apply.  
Dividends are generally not taxable until paid.  However, in limited circumstances certain
preferred stock dividends may be accrued under rules similar to the rules for debt.  Also, a
shareholder may be treated as having received a dividend if his percentage stock ownership
increases as a result of the payment of dividends to other shareholders.
31
 
Tax-exempt investors
A tax-exempt investor (for example, a university endowment fund or a pension plan
investor) is generally not taxed on investment interest, subject to certain unrelated business
income tax (UBTI) rules for debt-financed income.
32
  This is true whether the debt is issued by a
C corporation or by any other entity.   
 Tax-exempt investors also are generally not subject to tax on sale of C corporation stock,
unless the stock investment is debt-financed.  
However, tax-exempt equity investors in a partnership are taxed as engaged in an
unrelated trade or business on their distributive share of partnership income from such a
business, as if they had conducted the business directly. And tax-exempt equity investors in an S
corporation (other than an ESOP investor) are taxed on their entire share of S corporation income
or gain on sale of the stock.
33
  
Foreign investors
Debt interests in U.S. entities
Although U.S.-source interest paid to a foreign investor is generally subject to a 30-
percent gross basis withholding tax, various exceptions exist in the Code and in bilateral income
                                               
29
  A C corporation is not an eligible S corporation shareholder and therefore cannot own S corporation
stock. 
30
  Sec. 751.
31
  Sec. 305(c).  Certain situations in which some shareholders receive cash and others experience an
increase in their percentage ownership can also cause both groups of shareholders to be treated as receiving a
dividend under that section. 
32
  Secs. 512, 514.
33
  Sec. 512(b). 11
tax treaties.
34
  Interest is generally derived from U.S. sources if it is paid by the United States or
any agency or instrumentality thereof, a State or any political subdivision thereof, or the District
of Columbia.  Interest is also from U.S. sources if it is paid by a noncorporate resident or a
domestic corporation on a bond, note, or other interest-bearing obligation.
35
  For this purpose, a
noncorporate resident includes a domestic partnership which at any time during the year was
engaged in a U.S. trade or business.
36
  Additionally, interest paid by the U.S. branch of a foreign
corporation is also treated as U.S.-source income.
37
Statutory exceptions to this general rule apply for interest on bank deposits as well as
portfolio interest.  Interest on bank deposits may qualify for exemption on two grounds,
depending on where the underlying principal is held on deposit.  Interest paid with respect to
deposits with domestic banks and savings and loan associations, and certain amounts held by
insurance companies, are U.S.-source income but are not subject to the U.S. withholding tax
when paid to a foreign person, unless the interest is effectively connected with a U.S. trade or
business of the recipient.
38
  Interest on deposits with foreign branches of domestic banks and
domestic savings and loan associations is not treated as U.S.-source income and is thus exempt
from U.S. withholding tax (regardless of whether the recipient is a U.S. or foreign person).
39
 
Similarly, interest and original issue discount on certain short-term obligations is also exempt
from U.S. withholding tax when paid to a foreign person.
40
  
Portfolio interest received by a nonresident individual or foreign corporation from
sources within the United States is exempt from U.S. withholding tax.
41
  For obligations issued
before March 19, 2012, the term “portfolio interest” means any interest (including original issue
                                               
34
  Where a foreign investor is engaged in a U.S. trade or business, any U.S. source interest income or U.S.
source dividend income (see “Equity interest in U.S. Entities” below) derived from assets used in or held for use in
the conduct of the U.S. trade or business where the activities of the trade or business were material factor in the
realization of such income will be treated as effectively connected with that U.S. trade or business.  Sec. 864(a)(2).  
35
  Sec. 861(a)(1); Treas. Reg. sec. 1.861-2(a)(1).  However, special rules apply to treat as foreign source
certain amounts paid on deposits with foreign commercial banking branches of U.S. corporations or partnerships and
certain other amounts paid by foreign branches of domestic financial institutions.  Sec. 861(a)(1).  Prior to January
1, 2011, all (or a portion) of a payment of interest by a resident alien individual or domestic corporation was treated
as foreign source if such individual or corporation met an 80-percent foreign business requirement.  This provision
was generally repealed for tax years beginning after December 31, 2010.  
36
  Treas. Reg. sec. 1.861-2(a)(2).
37
  Sec. 884(f)(1).
38
  Secs. 871(i)(2)(A), 881(d); Treas. Reg. sec. 1.1441-1(b)(4)(ii).  
39
  Sec. 861(a)(1)(B); Treas. Reg. sec. 1.1441-1(b)(4)(iii).  
40
  Secs. 871(g)(1)(B), 881(a)(3); Treas. Reg. sec. 1.1441-1(b)(4)(iv).
41
  Secs. 871(h), 881(c).  In 1984, to facilitate access to the global market for U.S. dollar-denominated debt
obligations, Congress repealed the withholding tax on portfolio interest paid on debt obligations issued by U.S.
persons.  See Joint Committee on Taxation, General Explanation of the Revenue Provisions of the Deficit Reduction
Act of 1984 (JCS-41-84), December 31, 1984, pp. 391-92. 12
discount) that is paid on an obligation that is in registered form and for which the beneficial
owner has provided to the U.S. withholding agent a statement certifying that the beneficial owner
is not a U.S. person, as well as interest paid on an obligation that is not in registered form and
that meets the foreign targeting requirements of section 163(f)(2)(B).  Portfolio interest,
however, does not include interest received by a 10-percent shareholder,
42
 certain contingent
interest,
43
 interest received by a controlled foreign corporation from a related person,
44
 or interest
received by a bank on an extension of credit made pursuant to a loan agreement entered into in
the ordinary course of its trade or business.
45
For obligations issued after March 18, 2012, the term “portfolio interest” no longer
includes interest paid with respect to an obligation not in registered form. This narrowing of the
scope of the portfolio interest exemption is a result of the repeal of the exception to the
registration requirements for foreign targeted securities in 2010, effective for obligations issued
two years after enactment.
46
 
U.S.-source interest payments that do not qualify for a statutory exemption from the 30-
percent withholding tax often are exempt from withholding under U.S. bilateral income tax
treaties.  Many treaties, including, for example, those with Canada, Germany, and the United
Kingdom, broadly eliminate the withholding tax on U.S.-source interest payments.  The result is
that large volumes of interest payments are exempt from withholding under the Code or a treaty.
Equity interests in U.S. entities
A foreign equity investor’s receipt of U.S.-source dividend income from a U.S. domestic
corporation is generally subject to a 30-percent gross basis withholding tax.  Dividend income is
generally sourced by reference to the payor’s place of incorporation such that dividends paid by
a domestic corporation are generally treated as entirely U.S.-source income.
 47
  As with interest,
the 30-percent withholding tax on dividends received by foreign investors may be reduced or
eliminated under U.S. bilateral income tax treaties.  In general, the dividend withholding tax
rates in treaties vary based on the percentage of stock of the dividend-paying company owned by
the recipient of the dividend.  Treaties typically provide lower withholding tax rates (five
percent, for example) at ownership levels of ten percent and greater.  Twelve treaties, including
those with Germany, Japan, and the United Kingdom, eliminate the withholding tax on dividends
in circumstances in which, among other requirements, the foreign treaty resident is a company
that owns at least 80 percent (in the case of Japan, 50 percent) of the U.S. corporation paying the
dividend.
                                               
42
  Sec. 871(h)(3).
43
  Sec. 871(h)(4).
44
  Sec. 881(c)(3)(C).
45
  Sec. 881(c)(3)(A).
46
  Hiring Incentives to Restore Employment Law of 2010, Pub. L. No. 111-147, sec. 502(b).     
47
  Secs. 861(a)(2), 862(a)(2). 13
Foreign investors also are not generally subject to tax on the sale of C corporation
stock.
48
 
In contrast, a foreign equity investor in a partnership is taxed on its distributable share of
income effectively connected with the conduct of a U.S. trade or business, as if it had conducted
that business directly.  S corporations are not permitted to have foreign investors. 
Treatment if investment becomes worthless
A taxable holder of either debt or equity held as an investment generally recognizes a
capital loss if the instrument is sold to an unrelated party at a loss.
49
  Capital losses can generally
offset only capital gains; however, an individual may deduct up to $3,000 per year of capital loss
against ordinary income.  
A taxable holder of investment equity or debt also generally realizes a capital loss if the
instrument becomes worthless. Certain other transactions, such as liquidating a subsidiary,
50
 can
permit recognition of a stock loss without a sale to an unrelated party. 
In certain circumstances, an individual holder of debt that is not a security may take an
ordinary bad debt loss.
51
  
3. Acquisitions and dispositions
The Code permits certain corporate acquisitions and dispositions to occur without
recognition of gain or loss, generally so long as only equity interests are received or any
securities received do not exceed the amount surrendered.
52
  Similarly, the Code permits certain
contributions and distributions of property to and from partnerships without tax if made with
respect to an equity interest.
53
                                               
48
  Secs. 871 and 881, applicable to income not connected with a U.S. business.  The exemption does not
apply to a foreign individual who is present in the U.S. for 183 days or more during the taxable year.  Foreign
investors may be subject to tax if the stock is a U.S. real property interest under the Foreign Investment in Real
Property Tax Act of 1980 (“FIRPTA”). Sec. 897.
49
  Up to $50,000 of loss on certain small business company stock ($100,000 for a couple filing a joint
return) can be deducted as an ordinary loss. Sec. 1244.   
50
  See Sec. 267(a)(1), second sentence.
51
  Sec. 166.
52
  Secs. 351-368 and sec. 1032.
53
  Secs. 721 and 731.  14
A transfer of property to a corporation or partnership in exchange for debt of the entity is
generally treated as a sale of the property.
54
  Gain or loss is recognized, except that loss may be
deferred if the transfer is to a related party.
55
  
                                               
54
  Sec. 1001.   Special rules may apply if the transfer is considered part of a larger transaction such as an
otherwise tax-free corporate reorganization.  
55
  Secs. 267 and 707.  15
B. Definition of Debt and Equity
1. Distinguishing debt from equity  
In general
The characterization of an instrument as debt or equity for Federal income tax purposes is
generally determined by the substance of the investor’s investment.  An instrument’s
characterization depends upon the terms of the instrument and all the surrounding facts and
circumstances analyzed in terms of economic and practical realities.  Neither the form of the
instrument nor the taxpayer’s characterization of the interest is necessarily determinative of the
instrument’s treatment for Federal income tax purposes.  Nonetheless, between the extremes of
instruments that are clearly debt or clearly equity, taxpayers have some latitude to structure
instruments incorporating both debt- and equity-like features (commonly referred to as “hybrid
securities”).
56
There is currently no definition in the Code or Treasury regulations that can be used to
determine whether an interest in a corporation constitutes debt or equity for tax purposes. 
Moreover, the IRS will ordinarily not provide individual taxpayers guidance on whether an
interest in a corporation is debt or equity for tax purposes because, in its view, the issue is
primarily one of fact.
57
  
In the absence of statutory or regulatory standards, a substantial body of Federal common
law is the principal source of guidance for distinguishing debt and equity.  Courts generally agree
that the proper characterization of an instrument requires a facts and circumstances analysis, the
primary goal of which is to determine whether, in both substance and form, an instrument
represents risk capital entirely subject to the fortunes of the venture (equity),
58
 or an unqualified
promise to pay a sum certain on a specified date with fixed interest (debt).
59
  The determination
                                               
56
  See Kraft Foods Co. v. Commissioner, 232 F.2d 118, 123 (2d Cir. 1956) (noting that “[t]he vast majority
of these cases have involved ‘hybrid securities’ - instruments which had some of the characteristics of a
conventional debt issue and some of the characteristics of a conventional equity issue.”).
57
  Rev. Proc. 2011-3, sec. 4.02(1), 2011-1 I.R.B. 111.  The IRS has identified factors to weigh in
determining whether a particular instrument should be treated as debt or equity.  See, e.g., Notice 94-47, 1994-1
C.B. 357.
58
  See, e.g., United States v. Title Guarantee & Trust Co., 133 F.2d 990, 993 (6
th
 Cir. 1943) (noting that
“[t]he essential difference between a stockholder and a creditor is that the stockholder’s intention is to embark upon
the corporate adventure, taking the risks of loss attendant upon it, so that he may enjoy the chances of profit.”);
Farley Realty Corp. v. Commissioner, 279 F.2d 701 (2d Cir. 1960); Commissioner v. O.P.P. Holding Corp., 76 F.2d
11, 12 (2d Cir. 1935) (noting that that the distinction between the shareholder and the creditor is that “[t]he
shareholder is an adventurer in the corporate business; he takes the risk and profits from success [while] [t]he
creditor, in compensation for not sharing the profits, is to be paid independently of the risk of success, and gets a
right to dip into the capital when the payment date arrives.”).
59
  Gilbert v. Commissioner, 248 F.2d 399, 402 (2d Cir. 1957) (noting that debt involves “an unqualified
obligation to pay a sum certain at a reasonably close fixed maturity date along with a fixed percentage in interest
payable regardless of the debtor’s income or the lack thereof.”); sec. 385(b)(1) (“a written unconditional promise to
pay on demand or an a specified date a sum certain in money in return for an adequate consideration in money or 16
of whether an interest constitutes debt or equity is generally made by analyzing and weighing the
relevant facts and circumstances of each case.
60
Courts have created differing (though generally similar) lists of factors
61
 to distinguish
debt from equity with no one factor controlling or more important than any other.
62
  One
commentator provides a list of thirty factors along with the Circuit courts that have considered
these factors.
63
  Another commentator groups the factors discussed in the cases into four
categories:  (1) those involving the formal rights and remedies of the parties; (2) those bearing on
the genuineness of the alleged intention to create a debtor-creditor relationship; (3) those bearing
on the reasonableness or economic reality of that intention (the risk element); and (4) those
which are merely rhetorical expressions of a result, having no proper evidentiary weight in
themselves.
64
Some commonly cited factors considered, among others, are:
1. whether there is an unconditional promise to pay a sum certain on demand or at a
fixed maturity date in the reasonably foreseeable future; 
2. whether the holder possesses the right to enforce the payment of principal and interest;
3. whether there is subordination to, or preference over, any indebtedness of the issuer,
including general creditors;
                                               
money’s worth, and to pay a fixed rate of interest”); Treas. Reg. sec. 1.165-5(a)(3) (defines security as an evidence
of indebtedness to pay a fixed or determinable sum of money); sec. 1361(c)(5)(B) (straight-debt safe harbor for
subchapter S purposes).
60
  John Kelley Co. v. Commissioner, 326 U.S. 489 (1943) (stating “[t]here is no one characteristic, not even
the exclusion from management, which can be said to be decisive in the determination of whether the obligations are
risk investments in the corporations or debts.”).
61
  See, e.g., Fin Hay Realty Realty Co. v. United States, 398 F.2d 694 (3d Cir. 1968) (sixteen factors);
Estate of Mixon v. United States, 464 F.2d 394 (5th Cir. 1972) (thirteen factors); Roth Steel Tube Co. v.
Commissioner, 800 F.2d 625 (6th Cir. 1986) (eleven factors); United States v. Uneco Inc., 532 F.2d 1204 (8th Cir.
1976) (ten factors).   
62
  Tyler v. Tomlinson, 414 F.2d 844, 848 (5th Cir. 1969) (noting that “[t]he object of the inquiry is not to
count factors, but to evaluate them”); Estate of Mixon v. United States, 464 F.2d 394, 402 (5th Cir. 1972) (noting
that the factors are not of equal significance and that no one factor is controlling).
63
  Christensen, “The Case for Reviewing Debt/Equity Determinations for Abuse of Discretion,” 74
University of Chicago Law Review 1309, 1313 (2007). 
64
  Plumb, “The Federal Income Tax Significance of Corporate Debt:  A Critical Analysis and a Proposal,”
26 Tax Law Review 369, 411-412 (1971).  According to a study of 126 Tax Court opinions issued from 1955 to
1987, seven factors were found to be conclusive of debt classification 97 percent of the time.  Robertson,
“Daughtrey & Burckel, Debt or Equity?  An Empirical Analysis of Tax Court Classification During the Period
1955-1987,” 47 Tax Notes 707 (1990). 17
4. the intent of the parties, including the name given the instrument by the parties and its
treatment for nontax purposes including financial accounting, regulatory, and rating
agency purposes; 
5. the issuer’s debt to equity ratio; 
6. whether the instrument holder is at risk of loss or has the opportunity to participate in
future profits;
7. whether the instrument provides the holder the right to participate in the management
of the issuer; 
8. the availability and terms of other credit sources;
9. the independence (or identity) between holders of equity and the holders of the
instrument in question;
10. whether there are requirements for collateral or other security to ensure the payment
of interest and principal; and
11. the holder’s expectation of repayment.  
2. Regulatory authority pursuant to section 385
Section 385 authorizes the Secretary of the Treasury to prescribe such regulations as may
be necessary or appropriate to determine whether an interest in a corporation should be
characterized as debt or equity (or as in part debt and in part equity) for Federal income tax
purposes.  Section 385(b) lists five factors which “may” be included in regulations prescribed
under the section as relevant to the debt/equity analysis.  Section 385(b) lists the factors as:
1. whether there is an unconditional written promise to pay on demand or on a specified
date a sum certain in money in return for an adequate consideration in money or
money’s worth, and to pay a fixed rate of interest; 
2. whether there is subordination to or preference over any indebtedness of the
corporation;
3. the corporation’s debt to equity ratio;
4. whether the interest is convertible into stock of the corporation; and
5. the relationship between the holdings of stock in the corporation and holdings of the
interest in question.  
As detailed below, regulations under section 385 were promulgated but withdrawn
without ever having taken effect.  The withdrawn regulations are not legally binding on the IRS
or taxpayers.     18
Section 385(c) provides that an issuer’s characterization of an instrument (at the time of
issuance) is binding on the issuer and any holder, but not the Secretary.  However, the holder of
an instrument may treat an instrument differently than the issuer provided the holder discloses
the inconsistent treatment on his return.   
Legislative Background
Section 385 was enacted by the Tax Reform Act of 1969.
65
  The Senate Finance
Committee noted that: 
“In view of the uncertainties and difficulties which the distinction between debt
and equity has produced in numerous situations other than those involving
corporate acquisitions, the committee further believes that it would be desirable to
provide rules for distinguishing debt from equity in the variety of contexts in
which this problem can arise. The differing circumstances which characterize these
situations, however, would make it difficult for the committee to provide
comprehensive and specific statutory rules of universal and equal applicability. In
view of this, the committee believes it is appropriate to specifically authorize the
Secretary of the Treasury to prescribe the appropriate rules for distinguishing debt
from equity in these different situations.”
66
The Treasury promulgated proposed regulations under section 385 in March of 1980
67
and final regulations on December 31, 1980, with an effective date of April 30, 1981.  The
effective date was extended twice.
68
  The Treasury promulgated proposed amendments to the
regulations in 1982.
69
  The effective date of the proposed amendments, and the final regulations,
                                               
65
  Pub. L. No. 91-172.
66
  S. Rep. No. 91-552 (November 21, 1969).  The Senate Finance Committee previously considered
whether to define debt and equity in the context of creating the Internal Revenue Code of 1954.  At that time the
issue was whether the Senate should adopt the House of Representatives’ draft version of the Code which defined
participating stock (common stock) and nonparticipating stock (preferred stock) and defined the term security.  The
Senate Finance Committee ultimately recommended that these definitions be dropped, noting:  
Your committee believes that any attempt to write into the statute precise definitions which will classify
for tax purposes the many types of corporate stocks and securities will be frustrated by the numerous
characteristics of an interchangeable nature which can be given to these instruments.  Accordingly, your
committee has returned to the use of the terms “stock,” “common stock,” “securities,” etc., and, as is the
case under existing law, has not attempted to define them in the statute.  S. Rep. No. 1622, 83 Cong., 2d
Sess. 42 (1954).
67
  45 F.R. 18957.
68
  T.D. 7747, 45 F.R. 86438; T.D. 7774, 46 F.R. 24945; T.D. 7801, 47 F.R. 147.
69
  See 47 F.R. 164. 19
were again postponed.
70
 The final regulations were withdrawn in 1983 without ever having taken
effect.
71
   
Section 385 was amended by the Omnibus Budget Reconciliation Act of 1989
72
 to
specifically add authority for the Secretary to treat an interest in a corporation as part stock and
part debt.
73
  In 1992, section 385 was amended to add section 385(c) regarding the effect of an
issuer’s classification.
74
  
                                               
70
  T.D. 7822, 47 F.R. 28915.
71
  T.D. 7920, 48 F.R. 50711.  One commentator suggests that the regulations were not finalized because
tax planners could design instruments contained all of the essential features of equity but which qualify as debt
under the regulations.  As an example, he noted that an instrument would be classified as debt if its debt features
accounted for more than half of its value and that as a result of this rule, hybrid instruments such as adjustable rate
convertible notes began appearing that provided for guaranteed payments having a present value just greater than
half of the issue price, variable payments tied to the issuer’s common-stock dividends, and an option to convert
these instruments into shares of the issuer’s stock.  Adam O. Emmerich, “Hybrid Instruments and the Debt-Equity
Distinction in Corporate Taxation,” 52 University of Chicago Law Review 118, 129-131 (1985).
72
  Pub. L. No. 101-239.
73
  Section 7208(a)(2) of Pub. L. No. 101-239 provides that the authority granted to bifurcate an interest in a
corporation may not be applied retroactively.  
74
  Energy Policy Act of 1992, Pub. L. No. 102-486. 20
C. Rules to Address Stripping of U.S. Corporate Tax Base
in the Case of Nontaxed Holders
A taxable corporation may reduce its Federal income tax through the payment of
deductible amounts such as interest, rents, royalties, premiums, management fees to an affiliate
not subject to Federal income tax.  Sheltering or offsetting income otherwise subject to Federal
income tax in this manner is known as “earnings stripping.”  Several provisions of present law
limit taxpayers’ ability to strip earnings.  Following is a brief description of certain rules
designed to limit the ability of corporations to strip earnings using payments of interest.  
1. Earnings stripping
Present Law
Section 163(j) may disallow a deduction for disqualified interest paid or accrued by a
corporation in a taxable year if two threshold tests are satisfied:  the payor’s debt-to-equity ratio
exceeds 1.5 to 1 (the safe harbor ratio); and the payor’s net interest expense exceeds 50 percent
of its adjusted taxable income (generally, taxable income computed without regard to deductions
for net interest expense, net operating losses, domestic production activities under section 199,
depreciation, amortization, and depletion).  Disqualified interest includes interest paid or accrued
to:  (1) related parties when no Federal income tax is imposed with respect to such interest;
75
 (2)
unrelated parties in certain instances in which a related party guarantees the debt; or (3) to a real
estate investment trust (“REIT”) by a taxable REIT subsidiary of that trust.
76
  Interest amounts
disallowed under these rules can be carried forward indefinitely.
77
  In addition, any excess
limitation (i.e., the excess, if any, of 50 percent of the adjusted taxable income of the payor over
the payor’s net interest expense) can be carried forward three years.
78
The operation of these rules is illustrated by the following example.  ForCo, a corporation
organized in country A, wholly owns USCo, a corporation organized in the United States. 
ForCo’s investment in USCo stock totals $6.5 million.  In addition, USCo has borrowed $8
million from ForCo and $5 million from Bank, an unrelated bank.  In 2010, USCo’s first year of
operation, USCo’s adjusted taxable income is $1 million (none of which is from interest
income), and it also pays $400,000 of interest to ForCo and $300,000 of interest to the unrelated
bank.  Under the U.S.-country A income tax treaty, no tax is owed to the United States on the
interest payments made by USCo to ForCo.  
                                               
75
  If a tax treaty reduces the rate of tax on interest paid or accrued by the taxpayer, the interest is treated as
interest on which no Federal income tax is imposed to the extent of the same proportion of such interest as the rate
of tax imposed without regard to the treaty, reduced by the rate of tax imposed by the treaty, bears to the rate of tax
imposed without regard to the treaty. Sec. 163(j)(5)(B). 
76
  Sec. 163(j)(3). 
77
  Sec. 163(j)(1)(B).  
78
  Sec. 163(j)(2)(B)(ii).   21
 USCo has a 2:1 debt-to-equity ratio (total borrowings of $13 million ($8 million + $5
million) and total equity of $6.5 million), so USCo’s deduction for the $700,000
($400,000 + $300,000) of interest it paid may be limited.
 USCo’s disqualified interest is $400,000 (the amount of interest paid to a related
party on which no Federal income tax is imposed).
 USCo’s excess interest expense is $200,000 ($700,000 - ($1 million x 50%)).
 Accordingly, USCo may deduct only $500,000 ($700,000 - $200,000) for interest
expense in year 2010.
The $200,000 of excess interest expense may be carried forward and deducted in a
subsequent tax year with excess limitation.
Legislative Background
Section 163(j) was enacted in 1989 in response to Congressional concerns over earnings
stripping.
79
  Congress believed it was “appropriate to limit the deduction for interest that a
taxable person pays or accrues to a tax-exempt entity whose economic interests coincide with
those of the payor.  To allow an unlimited deduction for such interest permits significant erosion
of the tax base.”
80
In 1993, the earnings stripping rules were amended so that they applied to interest paid on
unrelated party loans if guaranteed by a related party under certain circumstances.
81
  Congress
made this change because it was concerned about the distinction made under the existing
earnings stripping rules between the situation in which unrelated creditors all lend to the parent
of a group, which in turn lends to the U.S. subsidiary, and the situation in which the creditors
lend directly to the U.S. subsidiary with a guarantee from the parent.
82
  The existing rules applied
to the first situation but not the second situation, even though the “same ‘excess’ interest
deductions, and the same resultant ‘shifting’ of net income out of U.S. taxing jurisdiction, is
obtainable through borrowing by U.S. corporations on [the parent’s] credit.”
83
                                               
79
  Revenue Reconciliation Act of 1989, Pub. L. No. 101-239, sec. 7210.
80
  H.R. Rep. No. 101-247, p. 1241 (1989).
81
  Revenue Reconciliation Act of 1993, Pub. L. No. 103-66, sec. 13228.
82
  H.R. Rep. No. 103-111, p. 683 (1993).
83
  Ibid., p. 682. 22
The definition of disqualified interest was expanded in 1999 to include interest paid or
accrued by a taxable REIT subsidiary to a related REIT.
84
In 2006, the earnings stripping rules were modified to apply to corporate owners of
partnership interests.
85
  Specifically, the modifications provided that for purposes of applying the
earnings stripping rules when a corporation owns an interest in a partnership, (1) the
corporation’s share of partnership liabilities are treated as liabilities of the corporation, and (2)
the corporation’s distributive share of interest income and interest expense of the partnership is
treated as interest income or interest expense, respectively, of the corporation.  Treasury was also
granted expanded regulatory authority to reallocate shares of partnership debt, or distributive
shares of the partnership’s interest income or interest expense.
The American Jobs Creation Act of 2004 required the Secretary of the Treasury to submit
a report to the Congress by June 30, 2005, examining the effectiveness of the earnings stripping
provisions of present law, including specific recommendations to improve the provisions of the
Code applicable to earnings stripping.
86
  The Treasury Department submitted its report to
Congress on November 28, 2007.
87
  In summary, the report concludes that “[t]here is strong
evidence that [inverted corporations]
88
 are stripping a significant amount of earnings out of their
U.S. operations and, consequently, it would appear that section 163(j) is ineffective in preventing
them from engaging in earnings stripping.”
89
  The report also concludes, however, that the
evidence that other foreign-controlled domestic corporations are engaged in earnings stripping is
not conclusive, and that it is not possible to determine with precision whether section 163(j) is
effective generally in preventing earnings stripping by foreign-controlled domestic
corporations.
90
                                               
84
  Tax Relief Extension Act of 1999, Pub. L. No. 106-170, sec. 544.  Technical corrections were also made
in 1996 and 2005.  Small Business Job Protection Act of 1996, Pub. L. No. 104-188, secs. 1703(n)(4), 1704(f)(2);
Gulf Opportunity Zone Act of 2005, Pub. L. No. 109-135, sec. 403(a)(15).
85
  Tax Increase Prevention and Reconciliation Act of 2005, Pub. L. No. 109-222, sec. 501 (2006).
86
  Pub. L. No. 108-357, sec. 424.
87
  U.S. Department of the Treasury, Report to Congress on Earnings Stripping, Transfer Pricing and U.S.
Income Tax Treaties (2007).  For a detailed discussion of the report, including an analysis of its methodology and
conclusions, see Joint Committee on Taxation, Description of Revenue Provisions Contained in the President’s
Fiscal Year 2012 Budget Proposal (JCS-3-11), June 2011, pp. 259-65.
88
  An “inverted corporation” is a former U.S.-based multinational that restructured to replace a U.S. parent
corporation with a new foreign parent for the group.   For purposes of the Treasury report, inverted corporations are
a subset of foreign-controlled domestic corporations. 
89
  U.S. Department of the Treasury, Report to Congress on Earnings Stripping, Transfer Pricing and U.S.
Income Tax Treaties (2007), p. 26.
90
  Ibid., pp. 25-26. 23
Subsequent to its 2007 report on earnings stripping, the Treasury Department created a
new tax form, Form 8926 Disqualified Corporate Interest Expense Disallowed Under Section
163(j) and Related Information, to collect information related to earnings stripping.  Form 8926
must be filed by a corporation (other than an S corporation) if it paid or accrued disqualified
interest during the taxable year or had a carryforward of disqualified interest from a previous tax
year.
2. Tax treatment of certain payments to controlling exempt organizations
Present Law
Although tax-exempt organizations described under section 501(c) are generally exempt
from Federal income tax,
91
 such organizations may be subject to the unrelated business income
tax (UBIT)
92
 on interest and other income received from the organization’s controlled
subsidiaries.
93
  Section 512(b)(13) subjects interest income (as well as rent, royalty, and annuity
income) to UBIT if such income is received from a taxable or tax-exempt subsidiary that is 50-
percent controlled by the parent tax-exempt organization to the extent the payment reduces the
net unrelated income (or increases any net unrelated loss) of the controlled entity (determined as
if the entity were tax-exempt).
94
  
A special rule relaxes the general rule of section 512(b)(13) for qualifying specified
payments made pursuant to a binding written contract that was in effect on August 17, 2006 (or
renewal of such a contract on substantially similar terms).
95
  The special rule applies to payments
received or accrued before January 1, 2012.
                                               
91
  Sec. 501(a).
92
  Secs. 511-514. In general, UBIT taxes income derived from a regularly carried on trade or business that
is not substantially related to the organization’s exempt purposes. Certain categories of income—such as interest,
dividends, royalties, and rent—are generally exempt from UBIT.  For example, tax-exempt organizations are not
taxed on interest income they receive from investments in debt or other obligations. 
93
  Tax-exempt organizations subject to UBIT include those described in section 501(c) (except for U.S.
instrumentalities and certain charitable trusts), qualified pension, profit-sharing, and stock bonus plans described in
section 401(a), and certain State colleges and universities. Sec. 511(a)(2). Organizations liable for UBIT may be
liable for alternative minimum tax determined after taking into account adjustments and tax preference items.
94
  In the case of a stock subsidiary, “control” means ownership by vote or value of more than 50 percent of
the stock.  In the case of a partnership or other entity, “control” means ownership of more than 50 percent of the
profits, capital, or beneficial interests.  In addition, present law applies the constructive ownership rules of section
318 for purposes of section 512(b)(13).  Thus, a parent exempt organization is deemed to control any subsidiary in
which it holds more than 50 percent of the voting power or value, directly (as in the case of a first-tier subsidiary) or
indirectly (as in the case of a second-tier subsidiary).
95
  Sec. 512(b)(13)(E).  For such payments covered by the special rule, the general inclusion rule of section
512(b)(13) applies only to the portion of payments received or accrued in a taxable year that exceeds the amount of
the payment that would have been paid or accrued if the amount of such payment had been determined under the
principles of section 482 (i.e., at arm’s length).  In addition, the special rule imposes a 20-percent penalty on the
larger of such excess determined without regard to any amendment or supplement to a return of tax, or such excess
determined with regard to all such amendments and supplements. 24
Legislative Background
Congress enacted section 512(b)(13) as part of the Tax Reform Act of 1969
96
 for the
purpose of preventing organizations from avoiding taxation through arrangements in which a
taxable organization controlled by a tax-exempt organization would make deductible payments
of interest, rent, annuities, or royalties to the tax-exempt organization to reduce taxable income.
97
Congress amended section 512(b)(13) in 1997 to broaden the definition of control to capture
arrangements using constructive ownership and second-tier subsidiaries.
98
 
The Pension Protection Act of 2006 enacted the special rule for qualifying specified
payments under section 512(b)(13)(E).
 99
  The Tax Extenders and Alternative Minimum Tax
Relief Act of 2008 extended the special rule to such payments received or accrued before
January 1, 2009,
100
 and the Tax Relief, Unemployment Insurance Reauthorization, and Job
Creation Act of 2010
101
 extends the special rule to such payments received or accrued before
January 1, 2012.
  
                                               
96
  Pub. L. No. 91-172.
97
  See H.R. Rep. No. 413, 91
st
 Cong., 1
st
 Sess. 49 (1969).
98
  Tax Relief Act of 1997, Pub. L. No. 105-34.
99
  Pub. L. No. 109-280.
100
  Pub. L. No. 110-343.
101
  Pub. L. No. 111-312. 25
D. Rules to Address Corporate Base Erosion Without Regard
to Holders’ Tax Status
Several present-law rules limit interest deductions in circumstances in which it appears a
deduction would not be appropriate, for example, because the instrument more closely resembles
equity or because deductibility would otherwise allow an inappropriate reduction of the
corporate tax base.  The inappropriate reduction of the corporate tax base through the use of
deductible payments or other planning techniques is commonly referred to a “base erosion.” 
Some limitations on the deductibility of interest expense are linked to whether the recipient of
the interest is exempt from Federal tax (e.g., the earnings stripping limitation of section 163(j))
while others consider the timing of the borrower’s deduction matches the timing of the lender’s
corresponding income inclusion (e.g., the interest and OID rules of sections 267(a)(3) and
163(e)(3)).  Other interest deduction limitations apply without regard to holder’s tax status. 
Following is a brief description of some of these limitations.   
1. Corporate Equity Reduction Transactions
Present Law
A net operating loss (“NOL”) is the amount by which a taxpayer’s business deductions
exceed its income.  In general, an NOL may generally be carried back two years and carried
forward 20 years to offset taxable income in such years.
102
  NOLs offset taxable income in the
order of the taxable years to which the NOLs are carried.
103
  
Sections 172(b)(1)(E) and 172(h) limit the NOL carrybacks of a C corporation involved
in a corporate equity reduction transaction (a “CERT”) to the extent such NOL carryback is
attributable to interest deductions allocable to a CERT and is incurred (1) in the taxable year in
which the CERT occurs or (2) in either of the two succeeding taxable years.  The portion of the
corporation’s NOL carryback that is limited is the lesser of (a) the corporation’s interest expense
allocable to the CERT, or (b) the excess of the corporation’s interest expense in the loss
limitation year over the average of the corporation’s interest expense for the three taxable years
prior to the CERT taxable year.  Any portion of an NOL that cannot be carried back under the
provision may be carried forward as otherwise allowed.  
Except to the extent provided in regulations, interest is allocated to a CERT using the
“avoided cost” method of allocating interest in lieu of a direct tracing rule.
104
  That is, the
amount of indebtedness treated as incurred or continued to finance the CERT is based on the
amount of interest expense that would have been avoided if the CERT had not been undertaken
and the amounts expended for the CERT were used to repay indebtedness.  
                                               
102
  Sec. 172(b)(1)(A). 
103
  Sec. 172(b)(2). 
104
  Sec. 172(h)(2)(B) (adopting the avoided cost allocation method described in section 263A(f)(2)(A)(ii)
and not the direct tracing method described in section 263A(f)(2)(A)(i)).  26
A corporate equity reduction transaction means either a major stock acquisition or an
excess distribution.  A major stock acquisition is the acquisition by a corporation (or any group
of persons acting in concert with such corporation) of stock in another corporation representing
50 percent or more (by vote or value) of the stock of another corporation.
105
  A major stock
acquisition does not include a qualified stock purchase to which a section 338 election applies.
106
 
An excess distribution is the excess of the aggregate distributions and redemptions made by a
corporation during the taxable year with respect to its stock (other than certain preferred stock
described in section 1504(a)(4)), over the greater of (a) 150 percent of the average of such
distributions and redemptions for the preceding three taxable years, or (b) 10 percent of the fair
market value of the stock of such corporation as of the beginning of such taxable year.  The
amount of distributions and redemptions made by a corporation during a taxable year are reduced
by stock issued by the corporation during the applicable period in exchange for money or
property other than stock in the corporation.  
A corporation is treated as being involved in a CERT if it is either the acquired or
acquiring corporation, or successor thereto (in the case of a major stock acquisition) or the
distributing or redeeming corporation, or successor thereto (in the case of an excess distribution).
Legislative Background
The CERT provisions were added to the Code by the Omnibus Budget Reconciliation
Act of 1989
107
 because Congress believed that the ability of corporations to carry back NOLs
created by certain debt-financed transactions is contrary to the purpose of the NOL rules.  The
NOL carryover rules generally serve the purpose of smoothing swings in taxable income that can
result from business cycle fluctuations and unexpected financial reverses.  Congress believed
that the underlying nature of a corporation is substantially altered by a CERT, and that the
interest expense associated with such transaction lacks a sufficient nexus with prior period
operations to justify the carryback of NOLs attributable to such expense.
108
  The definition of a
CERT was expanded by the Omnibus Budget Reconciliation Act of 1990
109
 to include the
acquisition of 50 percent or more of the vote or value of the stock of any corporation, regardless
of whether the corporation was a member of an affiliated group (unless an election under section
338 were made). 
                                               
105
  Secs. 172(h)(3)(A)(i) and 172(h)(3)(B).  
106
  Sec. 172(h)(3)(B)(ii).  A section 338 election allows taxpayers to treat a qualifying stock acquisitions as
an asset acquisition for tax purposes.  
107
  Pub. L. No. 101-239.
108
  H.R. Rep. No. 101-247. 
109
  Pub. L. No. 101-508. 27
2. Debt expected to be paid in equity
Present Law
Section 163(l) generally disallows a deduction for interest or OID on a debt instrument
issued by a corporation (or issued by a partnership to the extent of its corporate partners) that is
payable in equity of the issuer or a related party (within the meaning of sections 267(b) and
707(b)), or equity held by the issuer (or a related party) in any other person.  
For this purpose, debt is treated as payable in equity if a substantial amount of the
principal or interest is mandatorily convertible or convertible at the issuer’s option into such
equity.  In addition, a debt instrument is treated as payable in equity if a substantial portion of the
principal or interest is required to be determined, or may be determined at the option of the issuer
or related party, by reference to the value of such equity.
110
  A debt instrument also is treated as
payable in equity if it is part of an arrangement that is reasonably expected to result in the
payment of the debt instrument with or by reference to such equity, such as in the case of certain
issuances of a forward contract in connection with the issuance of debt, nonrecourse debt that is
secured principally by such equity, or certain debt instruments that are paid in, converted to, or
determined with reference to the value of equity if it may be so required at the option of the
holder or a related party and there is a substantial certainty that the option will be exercised.
111
 
An exception is provided for debt issued by a dealer in securities (within the meaning of section
475) or a related party which is payable in, or by reference to, equity (not of the issuer or related
party) held in its capacity as a dealer in securities.
112
Application of section 163(l) to an instrument will generally disallow the issuer’s interest
or OID deductions, but the provision does not alter the treatment of amounts paid or accrued to
the holder.
113
Legislative Background
Section 163(l) was enacted by the Taxpayer Relief Act of 1997
114
 in response to
Congressional concern that corporate taxpayers could issue instruments denominated as debt, but
that more closely resembled equity for which an interest deduction is not appropriate.
115
  
The American Jobs Creation Act of 2004
116
 expanded the provision to disallow interest
deductions on certain corporate debt that is payable in, or by reference to the value of, any equity
                                               
110
  Sec. 163(l)(3)(B). 
111
  Sec. 163(l)(3)(C).
112
  Sec. 163(l)(5).  
113
  See H.R. Conf. Rep. 105-220.
114
  Pub. L. No. 105-34.
115
  H.R. Rep. No. 105-148.  28
held by the issuer (or any related party) in any other person, but provided for the dealers in
securities exception.  Prior to AJCA, section 163(l) operated to disallow a deduction with respect
to an instrument payable in stock of the issuer or an a related party (using a more than 50 percent
ownership test).  Expansion of the scope of section 163(l) was prompted, at least in part, by
transactions undertaken by Enron Corporation to effectively monetize affiliate stock.
117
  For
example, in 1995 Enron issued investment unit securities which provided for an amount payable
at maturity in stock of a more than 50-percent owned Enron affiliate.  In 1999, after the
enactment of section 163(l), Enron issued similar investment unit securities with respect to the
same corporate affiliate.  Enron took the position that section 163(l), however, did not apply
because Enron’s ownership of the affiliate had decreased below the 50-percent threshold.
118
 
Congress believed the Enron transactions cast doubt on the rule excluding stock ownership
interests of 50-percent or less.  Congress believed that eliminating the related party threshold
furthered the tax policy objective of similar tax treatment for economically similar
transactions.
119
3. Applicable high-yield discount obligations
Present Law
In general, the issuer of a debt instrument with OID may deduct the portion of such OID
equal to the aggregate daily portions of the OID for days during the taxable year.
120
  However, in
the case of an applicable high-yield discount obligation (an AHYDO) issued by a corporate
issuer, (1) no deduction is allowed for the “disqualified portion” of the OID on such obligation,
and (2) the remainder of the OID on any such obligation is not allowable as a deduction until
paid by the issuer.
121
  
An AHYDO is any debt instrument if (1) the maturity date on such instrument is more
than five years from the date of issue; (2) the yield to maturity on such instrument exceeds the
sum of (a) the applicable Federal rate in effect under section 1274(d) for the calendar month in
which the obligation is issued and (b) five percentage points, and (3) such instrument has
significant original issue discount.
122
  An instrument is treated as having significant OID if the
                                                
116
  Pub. L. No. 108-357.
117
  See S. Rep. No. 108-192. 
118
  For a discussion of the Enron transactions, see Joint Committee on Taxation, Report of Investigation of
Enron Corporation and Related Entities Regarding Federal Tax and Compensation Issues, and Policy
Recommendations (JCS-3-03), February 2003, pp. 333-345.
119
  S. Rep. No. 108-192.  
120
  Sec. 163(e)(1).  For purposes of section 163(e)(1), the daily portion of the original issue discount for
any day is determined under section 1272(a) (without regard to paragraph (7) thereof and without regard to section
1273(a)(3)). 
121
  Sec. 163(e)(5). 
122
  Sec. 163(i)(1).  29
aggregate amount of interest that would be includible in the gross income of the holder with
respect to such instrument for periods before the close of any accrual period (as defined in
section 1272(a)(5)) ending after the date five years after the date of issue exceeds the sum of (1)
the aggregate amount of interest to be paid under the instrument before the close of such accrual
period, and (2) the product of the issue price of such instrument (as defined in sections 1273(b)
and 1274(a)) and its yield to maturity.
123
  The disqualified portion of the OID on an AHYDO is
the lesser of (1) the amount of OID with respect to such obligation or (2) the portion of the total
return on such obligation which bears the same ratio to such total return as the disqualified yield
(i.e., the excess of the yield to maturity on the obligation over the applicable Federal rate plus six
percentage points) on such obligation bears to the yield to maturity on such obligation.
124
  The
term total return means the amount which would have been the original issue discount of the
obligation if interest described in section 1273(a)(2) were included in the stated redemption to
maturity.
125
  A corporate holder treats the disqualified portion of OID as a stock distribution for
purposes of the dividend received deduction.
126
 
Legislative Background
Sections 163(i) and 163(e)(5) were enacted by the Omnibus Budget Reconciliation Act of
1989,
127
 following a series of Congressional hearings on corporate leverage.  Congress enacted
the AHYDO rules because it believed that a portion of the return on certain high-yield OID
obligations is similar to a non-deductible distribution of corporate earnings paid with respect to
equity rather than a deductible payment of interest.
128
The American Recovery and Reinvestment Tax Act of 2009 (“ARRA”)
129
 suspended the
deduction denial and deferral rules of section 163(e)(5) for certain obligations issued in debt-fordebt exchanges (including deemed exchanges resulting from a significant modification) after
August 31, 2008 and before January 1, 2010.  ARRA also provided authority to the Secretary to
(1) apply the suspension rule for periods after December 31, 2009, where the Secretary
determines that such application is appropriate in light of distressed conditions in the debt capital
markets, and (2) use a rate that is higher than the applicable Federal rate for purposes of applying
section 165(e)(5) for obligations issued after December 31, 2009, in taxable years ending after
such date if the Secretary determines that such higher rate is appropriate in light of distressed
debt capital market conditions.  
                                               
123
  Sec. 163(i)(2).
124
  Sec. 163(e)(5)(C).
125
  Sec. 163(e)(5)(C)(ii).
126
  Sec. 163(e)(5)(B). 
127
  Pub. L. No. 101-239. 
128
  H.R. Conf. Rep. 101-386 (November 21, 1989). 
129
  Pub. L. No. 111-5. 30
4. Interest on certain acquisition indebtedness
Present Law
Section 279 denies a deduction for interest on “corporate acquisition indebtedness.”  The
limitation applies to interest in excess of $5 million per year incurred by a corporation with
respect to debt obligations issued to provide consideration for the acquisition of stock, or two
thirds of the assets, of another corporation, if each of the following conditions exists:  (1) the
debt is substantially subordinated;
130
 (2) the debt carries an equity participation feature
131
 (e.g.,
includes warrants to purchase stock of the issuer or is convertible into stock of the issuer); and
(3) either the issuer is thinly capitalized (i.e., has a debt-to-equity ratio that exceeds 2 to 1)
132
 or
projected annual earnings do not exceed three times annual interest costs (paid or incurred).
133
  
Legislative Background
Section 279 was enacted by the Tax Reform Act of 1969
134
 in response to concerns over
increased corporate acquisitions and the use of debt for such corporate acquisitions.
135
  In 1976,
the section was amended to delete the provision which would deny a deduction for interest on
corporate acquisition indebtedness where a corporation which had acquired at least 50 percent of
the total combined voting power of all classes of stock of another corporation by October 9,
1969, incurred acquisition indebtedness in increasing its control over the acquired corporation to
80 percent or more.
136
  
                                               
130
  Subordinated to the claims of trade creditors generally, or expressly subordinated in right of payment of
any substantial amount of unsecured indebtedness, whether outstanding or subsequently issued (sec.  279(b)(2)(A)
and (B)).
131
  Convertible directly or indirectly into the stock of the issuing corporation or part of an investment unit
or other arrangement which includes an option to acquire, directly or indirectly, stock in the issuing corporation (sec.
279(b)(3)(A) and (B)).
132
  Sec. 279(b)(4)(A). 
133
  Sec. 279(b)(4)(B).  
134
  Pub. L. No. 91-172.
135
  S. Rep. No. 91-552 (November 21, 1969).  See also, Joint Committee on Taxation, General
Explanation of the Tax Reform Act of 1969 (JCS-16-70), December 3, 1970, p. 123.
136
  Pub. L. No. 94-514. 31
E. Rules to Address Tax Arbitrage in the Case of Borrowing
to Fund Untaxed Income
When debt is used to finance an investment that produces income exempt from tax, taxed
at preferential rates, or carrying associated tax credits, the deduction for interest on the debt
financing can be used to offset other, unrelated income.  In addition, certain leveraged
transactions by entities exempt from tax may present the opportunity for taxpayers to engage in
transactions on terms they might not have in the absence of the tax-exemption.  These outcomes
are commonly referred to as “tax arbitrage.”  Following is a brief discussion of certain rules that
attempt to limit the ability of taxpayers to engage in these types of transactions.  
1. Interest related to tax-exempt income
Present Law
Section 265 disallows a deduction for interest on indebtedness incurred or continued to
purchase or carry obligations the interest on which is wholly exempt from Federal income tax
(“tax-exempt obligations”).  This rule applies to tax-exempt obligations held by individual and
corporate taxpayers.
137
  The rule also applies to certain cases in which a taxpayer incurs or
carries indebtedness and a related person acquires or holds tax-exempt obligations.
138
  Generally,
there are two methods for determining the amount of the disallowance.  One method asks
whether a taxpayer’s borrowing can be traced to its holding of exempt obligations.  A second
method disallows interest deductions based on the pro rata percentage of a taxpayer’s assets
comprised of tax-exempt obligations.
The interest expense disallowance rules are intended to prevent taxpayers from engaging
in tax arbitrage by deducting interest on indebtedness that is used to purchase tax-exempt
obligations, so that the interest is available to offset other taxable income of the taxpayer
General rules
Debt is traced to tax-exempt obligations if the proceeds of the indebtedness are used for,
and are directly traceable to, the purchase of tax-exempt obligations.  For example, this rule
applies if tax-exempt obligations are used as collateral for indebtedness.  In general terms, the
tracing rule applies only if the facts and circumstances establish a sufficiently direct relationship
between the borrowing and the investment in tax-exempt obligations.
                                                
137
  The rules applicable to individual taxpayers are discussed in the companion document, Tax Treatment
of Household Debt.
138
  Section 7701(f) provides that the Secretary of the Treasury will prescribe regulations necessary or
appropriate to prevent the avoidance of any income tax rules that deal with the use of related persons, pass-through
entities, or other intermediaries in (1) the linking of borrowing to investment or (2) diminishing risks.  See H
Enterprises International, Inc. v. Commissioner, T.C.M. 1998-97, aff’d. 183 F.3d 907 (8
th
 Cir. 1999) (Code section
265(a)(2) applied where a subsidiary borrowed funds on behalf of a parent and the parent used the funds to buy,
among other investments, tax-exempt securities). 32
Within the general framework of section 265, there are special rules for individuals,
dealers in tax-exempt obligations, corporations that are not dealers, and certain financial
institutions.  
Dealers in tax-exempt obligations
In the case of a dealer in tax-exempt obligations (whether a corporation, partnership or
sole proprietorship), if the proceeds are directly traceable to the purchase of tax-exempt
obligations, no interest on the indebtedness is deductible.
139
  If the use of the proceeds cannot be
directly traced, an allocable portion of the interest deduction is disallowed.  The amount of
interest disallowed is determined by the ratio of (1) the dealer’s average amount of tax-exempt
obligations held during the taxable year to (2) the average amount of the dealer’s total assets less
the amount of any indebtedness the interest on which is not subject to disallowance to any extent
under the provision.
140
Corporations that are not dealers in tax-exempt obligations
In the case of a business that is not a dealer in tax-exempt obligations, if there is direct
evidence of the purpose to purchase or carry tax-exempt obligations with the proceeds of
indebtedness, then no interest on the indebtedness is deductible.  In the absence of such direct
evidence, the IRS provides specific inference rules.  Generally, the purpose to purchase or carry
tax-exempt obligations will not be inferred with respect to indebtedness incurred to provide
funds for an active trade or business unless the borrowing is in excess of business needs.
141
  In
contrast, the purpose to carry tax-exempt obligations will be inferred (unless rebutted by other
evidence) where a taxpayer could reasonably have foreseen at the time of purchasing tax-exempt
obligations that indebtedness would have been incurred to meet future economic needs of an
ordinary, recurrent variety.
142
  
De minimis exception
In the absence of direct evidence linking an individual taxpayer’s indebtedness with the
purchase or carrying of tax-exempt obligations, taxpayers other than dealers may benefit from a
de minimis exception.
143
  The IRS takes the position that it will ordinarily not infer a purpose to
purchase or carry tax-exempt obligations if a taxpayer’s investment therein is “insubstantial.”
144
  
                                               
139
  Rev. Proc. 72-18, sec. 5.02.
140
  Ibid., secs. 5.02 and 7.02.
141
  Rev. Proc. 72-18, sec. 6.01.
142
  Rev. Proc. 72-18, sec. 6.02. 
143
  Rev. Proc. 72-18, sec. 3.05 provides that the insubstantial holding safe harbor is not available to dealers
in tax-exempt obligations. 
144
  Rev. Proc. 72-18, 1972-1 C.B. 740. 33
A corporation’s holdings of tax-exempt obligations are presumed to be insubstantial if the
average adjusted basis of the corporation’s tax-exempt obligations is two percent or less of the
average adjusted basis of all assets held in the active conduct of the corporation’s trade or
business.
If a corporation holds tax-exempt obligations (installment obligations, for example)
acquired in the ordinary course of its business in payment for services performed for, or goods
supplied to, State or local governments, and if those obligations are nonsalable, the interest
deduction disallowance rule generally does not apply.
145
  The theory underlying this rule is that a
corporation holding tax-exempt obligations in these circumstances has not incurred or carried
indebtedness for the purpose of acquiring those obligations.
Financial institutions
After taking into account any interest disallowance rules under general rules applicable to
other taxpayers,
146
 Section 265(b)(2) disallows a portion of a financial institution’s otherwise
allowable interest expense that is allocable to tax-exempt interest.  The amount of interest that is
disallowed is an amount of interest expense that equals the ratio of the financial institution’s
average adjusted bases of tax-exempt obligations acquired after August 7, 1986 to the average
adjusted bases of all the taxpayer’s assets (the “pro rata rule”).
147
  This allocation rule is
mandatory and cannot be rebutted by the taxpayer.  A financial institution, for this purpose, is
any person who accepts deposits from the public in the ordinary course of such person’s trade or
business, and is subject to Federal or State supervision as a financial institution or is a bank as
defined in section 585(a)(2).  
Exception for certain obligations of qualified small issuers
The general rule in section 265(b) denying financial institutions’ interest expense
deductions allocable to tax-exempt obligations does not apply to “qualified tax-exempt
obligations.”  Instead, only 20 percent of the interest expense allocable to such qualified taxexempt obligations is disallowed.
148
  A qualified tax-exempt obligation is a tax-exempt
obligation that is (1) issued after August 7, 1986, by a qualified small issuer, (2) is not a private
                                               
145
  Rev. Proc. 72-18, as modified by Rev. Proc. 87-53, 1987-2 C.B. 669.
146
  Including section 265(a) (see, sec. 265(b)(6)(A) and Joint Committee on Taxation, General Explanation
of the Tax Reform Act of 1986, (JCS-10-87), p. 563), but section 265(b)(6)(B) specifies that the disallowance rule of
section 265 is applied before the capitalization rule of section 263A (relating to the capitalization of certain
expenditures discussed above).   
147
  Sec. 265(b).
148
  Secs. 265(b)(3) and 291(a)(3).  Section 291(a)(3) reduces by 20 percent the amount allowable as a
deduction with respect to any financial institution preference item. Financial institution preference items include
interest on debt to carry tax-exempt obligations acquired after December 31, 1982, and before August 8, 1986. 
Section 265(b)(3) treats qualified tax-exempt obligations as if they were acquired on August 7, 1986. As a result, the
amount allowable as a deduction by a financial institution with respect to interest incurred to carry a qualified taxexempt obligation is reduced by 20 percent. 34
activity bond, and (3) is designated by the issuer as qualifying for the exception.  A qualified
small issuer is an issuer that reasonably anticipates that the amount of tax-exempt obligations
that it will issue during the calendar year will be $10 million or less.  The Code specifies
circumstances under which an issuer and all subordinate entities are aggregated.
149
  The special
rule for qualified small issuers also applies to certain aggregated issuances of tax-exempt
obligations in which more than one governmental entity receives benefits.
150
Composite issues (i.e., combined issues of bonds for different entities) qualify for the
“qualified tax-exempt obligation” exception only if the requirements of the exception are met
with respect to (1) the composite issue as a whole (determined by treating the composite issue as
a single issue) and (2) each separate lot of obligations that is part of the issue (determined by
treating each separate lot of obligations as a separate issue).
151
  Thus a composite issue may
qualify for the exception only if the composite issue itself does not exceed $10 million, and if
each issuer benefitting from the composite issue reasonably anticipates that it will not issue more
than $10 million of tax-exempt obligations during the calendar year, including through the
composite arrangement.
Special rules for obligations issued in 2009 and 2010
The American Recovery and Reinvestment Act of 2009 (“ARRA”) modified certain
provisions of section 265.  Tax-exempt obligations issued during 2009 or 2010 and held by a
financial institution, in an amount not to exceed two percent of the adjusted basis of the financial
institution’s assets, are not taken into account for the purpose of determining the portion of the
financial institution’s interest expense subject to the pro rata interest disallowance rule of section
265(b).  
In connection with this change, ARRA also amended section 291(e) to provide that taxexempt obligations issued during 2009 and 2010, and not taken into account for purposes of the
calculation of a financial institution’s interest expense subject to the pro rata interest
disallowance rule, are treated as having been acquired on August 7, 1986.  As a result, such
obligations are financial institution preference items, and the amount allowable as a deduction by
a financial institution with respect to interest incurred to carry such obligations is reduced by 20
percent. 
With respect to tax-exempt obligations issued during 2009 and 2010, ARRA relaxed
several rules related to qualified small issuers.
Legislative Background
A provision denying a deduction for interest incurred in connection with tax-exempt
obligations has been a part of the U.S. tax system since the Revenue Act of 1917, which allowed
                                               
149
  Sec. 265(b)(3)(E).
150
  Sec. 265(b)(3)(C)(iii).
151
  Sec. 265(b)(3)(F). 35
a deduction for “all interest paid within the year on his indebtedness except on indebtedness
incurred for the purchase of obligations or securities the interest upon which is exempt from
taxation under this title.”
152
  Prior to 1986, banks were largely exempted from section 265
pursuant to IRS rulings providing, inter alia, that interest paid to depositors was not interest
incurred or continued to carry tax-exempt obligations
153
 and that section 265 would generally not
apply to interest on indebtedness incurred by banks in the ordinary course of business absent a
direct connection between the borrowing and the tax-exempt investment.
154
  
As part of the Tax Reform Act of 1986,
155
 Congress amended section 265 to deny
financial institutions an interest deduction in direct proportion to their tax-exempt holdings. 
Congress believed that allowing financial institutions to deduct interest payments regardless of
tax-exempt holdings discriminated in favor of financial institutions at the expense of other
taxpayers, and Congress was concerned that financial institutions could drastically reduce their
tax liability using such rules.  Congress believed that a proportional disallowance rule was
appropriate because of the difficulty of tracing funds within a financial institution and the near
impossibility of assessing a financial institution’s purpose in accepting particular deposits.
156
2. Debt with respect to certain insurance products
Present Law
No Federal income tax generally is imposed on a policyholder with respect to the
earnings under a life insurance contract
157
 (“inside buildup”).
158
  Further, an exclusion from
                                               
152
  Section 1201(1) of the Revenue Act of 1917.  For a history of section 265, see George Craven,
“Disallowance of Interest Deduction to Owner of Tax-Exempt Bonds,” 24 Tax Lawyer 287 (1971). 
153
  Rev. Rul. 61-222, 1961-2 C.B. 58.
154
  Rev. Proc. 70-20.  
155
  Pub. L. No. 99-514.
156
  See Joint Committee on Taxation, General Explanation of the Tax Reform Act of 1986 (JCS-10-87),
May 4, 1987, pp. 562-3. 
157
  By contrast to the treatment of life insurance contracts, if a deferred annuity contract is held by a
corporation or by any other person that is not a natural person, the income on the contract is treated as ordinary
income accrued by the contract owner and is subject to current taxation.  The contract is not treated as an annuity
contract (sec. 72(u)).
158
  This favorable tax treatment is available only if a life insurance contract meets certain requirements
designed to limit the investment character of the contract (sec. 7702).  Distributions from a life insurance contract
(other than a modified endowment contract) that are made prior to the death of the insured generally are includible
in income, to the extent that the amounts distributed exceed the taxpayer’s basis in the contract for purposes of
determining income taxes, other than those imposed on insurance companies such distributions generally are treated
first as a tax-free recovery of basis, and then as income (sec. 72(e)).  In the case of a modified endowment contract,
however, in general, distributions are treated as income first, loans are treated as distributions (i.e., income rather
than basis recovery first), and an additional 10-percent tax is imposed on the income portion of distributions made
before age 59 1/2 and in certain other circumstances (secs. 72(e) and (v)).  A modified endowment contract is a life 36
Federal income tax is provided for amounts received under a life insurance contract paid by
reason of the death of the insured.
159
Present law imposes limitations on the deductibility of interest on debt with respect to life
insurance contracts.  These limitations address the potential for arbitrage that could arise in the
event that deductible interest expense relates to amounts excludable as inside buildup and as
death benefits under a life insurance contract.  
Interest paid or accrued with respect to the contract
No deduction is allowed for any amount paid or accrued on debt incurred or continued to
purchase or carry a single premium life insurance, annuity, or endowment contract (the “single
premium” deduction limitation).
160
  A contract is treated as a single premium contract if
substantially all the premiums on the contract are paid within a period of four years from the date
on which the contract is purchased or if an amount for payment of a substantial number of future
premiums is deposited with the insurer.
161
 
In addition, no deduction is allowed for any amount paid or accrued on debt incurred or
continued to purchase or carry a life insurance, annuity, or endowment contract pursuant to a
plan of purchase that contemplates the systematic direct or indirect borrowing of part or all of the
increases in the cash value of the contract (either from the insurer or otherwise).
162
  Several
exceptions are provided for this rule.  The deduction denial does not apply if (1) no part of four
of the annual premiums due during the initial seven year period is paid by means of such debt;
(2) if the total amounts to which the provision would apply in a taxable year does not exceed
$100; (3) if the amounts are paid or accrued because of financial hardship; or (4) if the
indebtedness is incurred in connection with the taxpayer’s trade or business.
163
   
Finally, no deduction is allowed for interest paid or accrued on any debt with respect to a
life insurance, annuity, or endowment contract covering the life of any individual,
164
 with a key
person insurance exception.
165
 
                                               
insurance contract that does not meet a statutory “7-pay” test, i.e., generally is funded more rapidly than a policy that
would provide paid-up future benefits after the payment of seven annual level premiums (sec. 7702A).
159
  Sec. 101(a).
160
  Sec. 264(a)(2). 
161
  Sec. 264(c).
162
  Sec. 264(a)(3).
163
  Sec. 264(d).  
164
  Sec. 264(a)(4).
165
  This provision limits interest deductibility in the case of such a contract covering any individual in
whom the taxpayer has an insurable interest under applicable State law when the contract is first issued, except as
otherwise provided under special rules with respect to key persons and pre-1986 contracts.  Under the key person 37
Pro rata interest deduction limitation
A pro rata interest deduction disallowance rule also applies.  This rule applies to interest
for which a deduction is not disallowed under the other interest deduction disallowance rules
relating to life insurance including, for example, interest on third-party debt that is not with
respect to a life insurance, annuity, or endowment contract.  Under this rule, in the case of a
taxpayer other than a natural person,
166
 no deduction is allowed for the portion of the taxpayer’s
interest expense that is allocable to unborrowed policy cash surrender values.
167
  Interest expense
is allocable to unborrowed policy cash values based on the ratio of (1) the taxpayer’s average
unborrowed policy cash values of life insurance, annuity and endowment contracts, to (2) the
sum of the average unborrowed cash values of life insurance, annuity, and endowment contracts,
plus the average adjusted bases of other assets.
Under the pro rata interest disallowance rule, an exception is provided for any contract
owned by an entity engaged in a trade or business, if the contract covers only one individual who
is an employee or is an officer, director, or 20-percent owner of the entity of the trade or
business.
168
  The exception also applies to a joint-life contract covering a 20-percent owner and
his or her spouse.  
An employer may exclude the death benefit under a contract insuring the life of an
employee if the insured was an employee at any time during the 12-month period before his or
her death, or if the insured is among the highest paid 35 percent of all employees.  Notice and
consent requirements must be satisfied.
Legislative Background
A limitation has applied to the deductibility of interest with respect to single premium life
insurance contracts since 1942.
169
  Additional interest deduction limitations with respect to life
insurance, annuity, and endowment contracts were added in 1964 and 1986.
170
  More recently,
                                               
exception (sec. 264(e)), otherwise nondeductible interest may be deductible, so long as it is interest paid or accrued
on debt with respect to a life insurance contract covering an individual who is a key person, to the extent that the
aggregate amount of the debt does not exceed $50,000.  Other special rules apply.
166
  See sec. 264(f)(5).  
167
  Sec. 264(f).  This applies to any life insurance, annuity or endowment contract issued after June 8,
1997.
168
  Sec. 264(f)(4).
169
  Current sec. 264(a)(2) (former sec. 24(a)(6) of the 1939 Code), enacted in the Revenue Act of 1942,
Pub. L. No. 753, 56 Stat. 798, sec. 129, 77th Cong., 2d Sess., October 21, 1942.
170
  Sec. 264(a)(3), enacted in the Revenue Act of 1964, Pub. L. No. 88-272, sec. 215, 88th Cong., 2d Sess.,
1964; sec. 264(a)(4) and (e)(1) (subsequently modified), enacted in the Tax Reform Act of 1986, Pub. L. No. 99-
514, sec. 1003, 99th Cong., 2d Sess., October 22, 1986.  In addition to interest deduction limitations, limitations are
imposed on the deductibility of premiums with respect to life insurance, annuity, and endowment contracts (sec.
264(a)(1)). 38
further interest deduction limitations with respect to such insurance contracts were added in 1996
and again in 1997.
171
  In general, these interest deduction limitations have been based in part on
concern over the opportunity for tax arbitrage, that is, the deductibility of interest expense with
respect to untaxed investment income (inside buildup) of the insurance contract.
172
For example, in enacting the interest deduction limitations in 1997, Congress expressed
concern about the tax arbitrage of deducting interest expense that funds untaxed income:
In addition, the Committee understands that taxpayers may be seeking new means
of deducting interest on debt that in substance funds the tax-free inside build-up
of life insurance or the tax-deferred inside buildup of annuity and endowment
contracts.  The Committee believes that present law was not intended to promote
tax arbitrage by allowing financial or other businesses that have the ongoing
ability to borrow funds from depositors, bondholders, investors or other lenders to
concurrently invest a portion of their assets in cash value life insurance contracts,
or endowment or annuity contracts.  Therefore, the bill provides that for taxpayers
other than natural persons, no deduction is allowed for the portion of the
taxpayer’s interest expense that is allocable to unborrowed policy cash values of
any life insurance policy or annuity or endowment contract issued after June 8,
1997.
173
In 2006, additional rules for excludability of death benefits under a life insurance contract
were added in the case of employer-owned life insurance contracts
174
 (generally, those contracts
insuring employees that are excepted from the pro rata interest deduction limitation).
175
  
                                               
171
  Current sec. 264(e), enacted in the Health Insurance Portability and Accountability Act of 1996, Pub. L.
No. 104-191, sec. 501, 104th Cong., 2d. Sess., July 31, 1996; and sec. 264(f), enacted in the Taxpayer Relief Act of
1997, Pub. L. No. 105-34, sec. 1084, 105th Cong., 1st Sess., July 30, 1997.
172
  For example, in enacting the 1964 interest deduction limitation, Congress stated, “The annual increase
in the cash value of the insurance policy to reflect interest earnings, which generally is not taxable to the taxpayer
either currently or otherwise, is likely to equal or exceed the net interest charges the taxpayer pays.  Thus, for
taxpayers in higher brackets, where the annual increment in the value of the policy, apart from the premiums,
exceeds the net interest cost of the borrowing, such policies can actually result in a net profit for those insured.” 
Revenue Act of 1963, Report of the Committee on Ways and Means, H.R. Rep. No. 749, 88th Cong., 1st Sess., page
61, September 13, 1963.  As a further example, following enactment of the 1986 interest deduction limitation, the
reasons for change included this statement: “This provision provides a cap on the deductibility of such interest,
rather than phasing out deductibility.  The provision was structured in this manner to allow small businesses to use
loans on life insurance policies for their employees as a source of short-term capital when necessary.  Congress did
not intend to allow these loans to be an unlimited tax shelter as under prior law.”  Joint Committee on Taxation,
General Explanation of the Tax Reform Act of 1986, JCS-10-87, p. 579, May 4, 1987.  
173
  Revenue Reconciliation Act of 1997 (as Reported by the Senate Committee on Finance), S. Rep. No.
105-33, 105th Cong., 1st Sess., p. 187, June 20, 1997 (footnotes omitted).
174
  Sec. 101(j).
175
  Pension Protection Act of 2006, Pub. L. No. 109-280. 39
3. Debt-financed income of tax-exempt organizations
Present Law
Although tax-exempt organizations described under section 501(c) are generally exempt
from Federal income tax,
176
 such organizations may be subject to the unrelated business income
tax (“UBIT”)
177
 on income derived from property financed with debt.
178
 
In general, income of a tax-exempt organization that is produced by debt-financed
property is treated as unrelated business taxable income in proportion to the amount of
acquisition indebtedness on the income-producing property.
179
  Certain educational
organizations, pension funds, title holding companies, and retirement income accounts are
eligible for an exception to the debt-financed income rules for investments in real property.
180
Legislative Background
Until the introduction of the UBIT in 1950, there was no statutory limitation on the
amount of business activity an exempt organization could conduct so long as the earnings from
the business were used for exempt purposes. In response to certain abusive transactions,
181
 
                                               
176
  Sec. 501(a).
177
  Secs. 511-514.  In general, UBIT taxes income derived from a regularly carried on trade or business
that is not substantially related to the organization’s exempt purposes.  Certain categories of income—such as
interest, dividends, royalties, and rent—are generally exempt from UBIT.  For example, tax-exempt organizations
are not taxed on interest income they receive from investments in debt or other obligations. 
178
  Tax-exempt organizations subject to UBIT include those described in section 501(c) (except for U.S.
instrumentalities and certain charitable trusts), qualified pension, profit-sharing, and stock bonus plans described in
section 401(a), and certain State colleges and universities. Sec. 511(a)(2).  Organizations liable for UBIT may be
liable for alternative minimum tax determined after taking into account adjustments and tax preference items.
179
  Acquisition indebtedness generally means the amount of unpaid indebtedness incurred by an
organization in acquiring or improving the property and indebtedness incurred either before or after acquisition or
improvement that would not have been incurred but for the acquisition or improvement of the property.  Sec.
514(c)(1).
180
  Sec. 514(c)(9)(A).  Additional requirements must be met for the real property exception to apply where
the real property is held by a partnership in which a qualified organization is a partner.  In addition to the real
property exception, acquisition indebtedness does not include (1) certain indebtedness incurred in the performance
or exercise of a purpose or function constituting the basis of the organization’s exemption, (2) obligations to pay
certain types of annuities, and (3) an obligation, to the extent it is insured by the Federal Housing Administration, to
finance the purchase, rehabilitation, or construction of housing for low- and moderate-income persons.  See secs.
514(c)(4), (5), and (6), respectively. 
181
  For example, in one type of transaction, a tax-exempt organization borrows the entire purchase price of
real property, purchases the property and leases it back to the seller under a long-term lease, and services the loan
with tax-free rental income from the lease. H.R. Rep. No. 2319, 81st Cong., 2d Sess. 38-39 (1950); S. Rep. No.
2375, 81st Cong., 2d Sess. 31-32 (1950).  40
Congress subjected charitable organizations (not including churches) and certain other exempt
organizations to tax on their unrelated business income as part of the Revenue Act of 1950.
182
 
The 1950 Act taxed as unrelated business income certain rents received in connection
with the leveraged sale and leaseback of real estate.
183
  This provision was a precursor to the
present-law tax on unrelated debt-financed income.
In the Tax Reform Act of 1969, Congress extended UBIT to all tax-exempt organizations
described in section 501(c) and 401(a) (except United States instrumentalities).
184
  In addition,
the 1969 Act expanded the tax on debt-financed income beyond rents from debt-financed
acquisitions of real property to encompass debt-financed income from interest, dividends, other
rents, royalties, and certain gains and losses from any type of property.
185
 
In the Miscellaneous Revenue Act of 1980, Congress enacted an exception to the debtfinanced income rules for certain real property investments by qualified pension trusts (the
progenitor of the real property exception).
186
 
In the Deficit Reduction Act of 1984, Congress extended the real property exception to
educational organizations and layered on additional conditions, including an absolute bar on
seller financing and an anti-abuse rule in the case of qualified organizations that were partners in
partnerships investing in debt-financed real property.
187
  In 1987, Congress further modified the
restrictions on partnerships of qualified organizations investing in debt-financed real property by
                                               
182
  Revenue Act of 1950, Pub. L. No. 81-814, sec. 301.  In 1951, Congress extended the UBIT to the
income of State colleges and universities.  Sec. 511(a)(2)(B).
183
  There was an exception for rental income from a lease of five years or less.  For a discussion of
Congress’s objections to such transactions, see H.R. Rep. No. 2319, 81st Cong., 2d Sess. 38-39 (1950); S. Rep. No.
2375, 81st Cong., 2d Sess. 31-32 (1950).
184
  Pub. L. No. 91-172.  The tax also applies to certain State colleges and universities and their wholly
owned subsidiaries. Sec. 511(a)(2)(B).
185
  For a discussion of the reason for the expanding the debt-financed income rules in 1969, see Joint
Committee on Taxation, General Explanation of the Tax Reform Act of 1969 (JCS-16-70), December 3, 1970, at 62.
186
  Pub. L. No. 96-605.  Congress believed that such an exception was warranted because “the exemption
for investment income of qualified retirement trusts is an essential tax incentive which is provided to tax-qualified
plans in order to enable them to accumulate funds to satisfy their exempt purpose—the payment of employee
benefits.” S. Rep. No. 96-1036, 96th Cong., 2d Sess. 29 (1980).  In addition, the exemption provided to pension
trusts was appropriate because, unlike other exempt organizations, the assets of such trusts eventually would be
“used to pay taxable benefits to individual recipients whereas the investment assets of other [exempt] organizations .
. . are not likely to be used for the purpose of providing benefits taxable at individual rates.” Ibid.  In other words,
the exemption for qualified trusts generally results only in deferral of tax; unlike the exemption for other
organizations.
187
  Pub. L. No. 38-369.  See Joint Committee on Taxation, General Explanation of the Revenue Provisions
of the Deficit Reduction Act of 1984 (JCS-41-84), December 31, 1984, at 1151. 41
enacting the fractions rule.
188
  In 1993, Congress relaxed some of the conditions required to meet
the real property exception.
189
4. Dividends received deduction reduction for debt-financed portfolio stock
Present Law
In general, a corporate shareholder is allowed a deduction equal to (1) 100 percent of
certain qualifying dividends received from a corporation in the same affiliated group as the
recipient;
190
 (2) 80 percent of the dividends received from a corporation if it owns at least 20
percent of the payee’s stock (by vote and value); and (3) 70 percent of dividends received from
other corporations.
191
  The purpose of the dividends received deduction is to reduce multiple
corporate-level taxation of income as it flows from the corporation that earns it to the ultimate
noncorporate shareholder.  
However, if dividends are paid on debt-financed stock, the combination of the dividends
received deduction and the interest deduction would enable corporate taxpayers to shelter
unrelated income.  Therefore, section 246A generally reduces the 80 percent and 70 percent
dividends received deduction so that the deduction is available, in effect, only with respect to
dividends attributable to that portion of the stock which is not debt-financed.
192
  Under
regulations prescribed by the Secretary, any reduction in the amount allowable as a dividends
received deduction under the rule is limited to the amount of the interest allocable to the
dividend.
193
                                               
188
  Sec. 514(c)(9)(B)(vi) & (E), enacted in section 10214 of The Revenue Act of 1987, Pub. L. No. 100-
203. The fractions rule generally is intended to prevent the shifting of disproportionate income or gains to taxexempt partners of the partnership or the shifting of disproportionate deductions, losses, or credits to taxable
partners. See H.R. Rep. No. 100-391, H.R. 3545, Report to accompany recommendations from the Committee on
Ways and Means, House of Representatives, October 26, 1987, p. 1076. Under the fractions rule, the allocation of
items to any partner that is a qualified organization cannot result in such partner having a share of the overall
partnership income for any taxable year greater than such partner’s share of overall partnership loss for the taxable
year for which such partner’s loss share will be the smallest. Sec. 514(c)(9)(E)(i)(I). A partnership generally must
satisfy the fractions rule both currently and for each taxable year of the partnership in which it holds debt-financed
property and has at least one partner that is a qualified organization. Treas. Reg. sec. 1.514(c)-2(b)(2)(i).
189
  See Omnibus Budget Reconciliation Act of 1993, Pub. L. No. 103-66.
190
  Sec. 243(a)(3) and (b).  An affiliated group generally consists of a common parent corporation and one
or more other corporations at least 80 percent of the stock of which (by vote and value) is owned by the common
parent or another member of the group.
191
  Sec. 243.  Section 245 allows a 70 percent, 80 percent and 100 percent deduction for a specified portion
of dividends received from certain foreign corporations.  Section 244 allows a dividends received deduction on
certain preferred stock of public utilities.  
192
  The reduction of the dividends received deduction may be viewed as a surrogate for limiting the interest
deduction.  
193
  Sec. 246A(e).  Treasury has not issued regulations under section 246A. 42
Section 246A applies to dividends on debt-financed “portfolio stock” of the recipient
corporation.  Stock of a corporation is portfolio stock unless specifically excluded.  Stock is not
portfolio stock if, as of the beginning of the ex-dividend date for the dividend involved, the
taxpayer owns stock (1) possessing at least 50 percent of the total combined voting power of all
classes of stock entitled to vote, and (2) having a value equal to at least 50 percent of the value of
all the stock, of such corporation.
194
  Portfolio stock is debt-financed if there is a direct
relationship between indebtedness and the portfolio stock.  The provision does not incorporate
any allocation or apportionment formula or fungibility concept.  
Legislative Background
Section 246A was enacted by the Deficit Reduction Act of 1984,
195
 in response to
concern that corporate taxpayers were borrowing money (giving rise to deductible interest
payments) to purchase portfolio stock that paid dividends (partially excluded from income by the
dividends received deduction), thus allowing such taxpayers to use the deduction for dividends
paid or accrued to shelter unrelated income.  Congress did not believe these two deductions were
intended to provide such shelter.
196
 
  
                                               
194
  The 50 percent threshold is reduced to 20 percent if five or fewer corporate stockholders own, directly
or indirectly, stock possessing at least 50 percent of the voting power and value of all the stock of such corporation. 
This rule was intended to exempt certain corporate joint ventures from the provision.  See, Joint Committee on
Taxation, General Explanation of the Revenue Provisions of the Deficit Reduction Act of 1984 (JCS-41-84),
December 31, 1984. 
195
  Pub. L. No. 98-369.
196
  See Joint Committee on Taxation, General Explanation of the Revenue Provisions of the Deficit
Reduction Act of 1984 (JCS-41-84), December 31, 1984, p. 128. 43
F. Rules to Match Timing of Tax Deduction and Income Inclusion Relating to Debt
Statutory limitations on the deductibility of interest expense apply in some cases in which
an immediate deduction would produce a mismatching of income and expense.  If the full
interest deduction is not permitted on a current basis, the deduction may be disallowed, deferred
until a later time, or required to be capitalized into the basis of related property.  Following is a
brief description of some rules designed to match the timing of income and deductions related to
debt.
1. Interest and OID on amounts payable to related foreign lenders 
Present Law
Special rules apply to a debt instrument issuer’s deduction for accrued but unpaid
interest, and accrued OID, owed to certain related persons.  These rules are generally designed to
match the issuer’s deduction with the holder’s corresponding income inclusion.
Accrued but unpaid interest
A number of rules limit deductions for losses, expenses, and interest with respect to
transactions between related persons.  In the case of unpaid stated interest and expenses of
related persons, where, by reason of a payee’s method of accounting, an amount is not includible
in the payee’s gross income until it is paid, but the unpaid amounts are deductible currently by
the payor, the amount generally is allowable as a deduction when such amount is includible in
the gross income of the payee.
197
  This rule is intended to prevent the mismatch of, for example,
a deduction for interest accrued by a taxpayer on the accrual method of accounting that is
payable to a related person on a cash method of accounting.  In the absence of this rule, the
issuer would take a deduction upon accrual of the obligation to pay interest (whether or not the
interest was actually paid), but a related holder would not take the interest into income until it is
paid.  
U.S.-source “fixed or determinable annual or periodical” income, including dividends,
interest, rents, royalties, and other similar income, is subject to a 30-percent gross-basis
withholding tax when paid to a foreign person.
198
  This withholding tax can create a mismatch
where, for example, a U.S. accrual-method taxpayer borrows amounts from a foreign
corporation.  In the absence of a special rule, the U.S. taxpayer would be allowed a deduction for
accrued interest annually even if no interest were actually paid, and the foreign corporate lender
would be subject to the 30-percent gross-basis withholding tax only when the interest was paid.
The Code directs the Treasury Secretary to issue regulations applying the matching principle in
this circumstance and other circumstances involving payments to related foreign persons.
199
 
                                               
197
  Sec. 267(a)(2). 
198
  Secs. 871, 881, 1441, 1442.
199
  Section 267(a)(3)(A). 44
With respect to stated interest and other expenses owed to related foreign corporations, Treasury
regulations require a taxpayer to use the cash method of accounting in deducting amounts owed
to related foreign persons (with an exception for income of a related foreign person that is
effectively connected with the conduct of a U.S. trade or business and that is not exempt from
taxation or subject to a reduced rate of taxation under a treaty obligation).
200
   
A foreign corporation’s foreign-source active business income generally is subject to
U.S. tax only when such income is distributed to any U.S. person owning stock of such
corporation.  Accordingly, a U.S. person conducting foreign operations through a foreign
corporation generally is subject to U.S. tax on the foreign corporation’s income only when the
income is repatriated to the United States through a dividend distribution.   However, certain
anti-deferral regimes may cause the U.S. person to be taxed on a current basis in the United
States with respect to certain categories of passive or highly mobile income earned by the foreign
corporations in which a U.S. person holds stock.  The main anti-deferral rules are the controlled
foreign corporation (“CFC”) rules of subpart F
201
 and the passive foreign investment company
(“PFIC”) rules.
202
  Section 267(a)(3)(B) provides special rules for items payable to a CFC or a
PFIC.  In general, with respect to any item payable to a related CFC or a PFIC, deductions for
amounts accrued but unpaid (whether by U.S. or foreign persons) are allowable only to the
extent that the amounts accrued by the payor are, for U.S. tax purposes, currently includible in
the income of the direct or indirect U.S. owners of the related foreign corporation under the
relevant inclusion rules.  Deductions that have accrued but are not allowable under this special
rule are allowed when the amounts are actually paid. 
Original issue discount 
Rules similar to those discussed above apply in the case of OID on debt instruments held
by a related foreign person.  In such case, section 163(e)(3)(A) disallows a deduction for any
portion of such OID until paid by the issuer (the “related-foreign-person rule”).
203
  This relatedforeign-person rule does not apply to the extent that the OID is effectively connected with the
foreign related person’s conduct of a U.S. trade or business (unless such OID is exempt from
taxation or is subject to a reduced rate of taxation under a treaty obligation).
204
 
In the case of any OID debt instrument held by a related foreign person which is a CFC
or a PFIC, deductions for accrued but unpaid OID are similarly allowable only to the extent that
                                               
200
  Treas. Reg. sec. 1.267(a)-3(b)(1), -3(c).   
201
  Secs. 951 – 964. 
202
  Secs. 1291 – 1298. 
203
  Sec. 163(e)(3)(A). 
204
  Sec. 163(e)(3)(A). 45
such OID is, for U.S. tax purposes, currently includible in the income of the direct or indirect
U.S. owners of the related foreign corporation.
205
  
Legislative Background
Section 163(e)(3) was enacted by the Deficit Reduction Act of 1984
206
 to address the
mismatch that occurred if a current deduction was allowed for the accrual of interest on an OID
instrument before the interest was actually paid.  The Conference Report notes that “there is no
justification for mismatching in the case of related-party OID debt.  Such mismatching allows an
economic entity that has divided itself into more than one legal entity to contract with itself at the
expense of the U.S. Government.”
207
 The section 267(a)(3) rule directing the Secretary of the Treasury to issue regulations
extending the matching principle to payments made to a non-U.S. person was enacted in the Tax
Reform Act of 1986. 
In 2004, as part of AJCA, Congress added the special rules for CFCs and PFICs because
prior law (which assumed there would be little material distortion in the matching of income and
deductions in the context of the these anti-deferral regimes) failed to take into account the
situation in which amounts are included in the income of a related foreign corporation but are not
currently included in the income of the foreign corporation’s U.S. shareholder(s).
2. Construction period interest
Present Law
Section 263A generally denies a deduction for costs incurred in manufacturing or
constructing tangible property, requiring that such costs be capitalized.  In particular, section
263A(f) provides that interest paid or incurred during the production period of certain types of
property, and that is allocable to the production of the property, must be capitalized into the
adjusted basis of such property.  Interest is allocable to the production of property for these
purposes if it is interest on debt that can be specifically traced to production expenditures.  If
production expenditures exceed the amount of the specifically traceable debt, then other interest
expense that the taxpayer would have avoided if amounts incurred for production expenditures
instead had been used to repay the debt also is treated as allocable to the production of property
(the “avoided cost” method of allocating interest).  Section 263A(f) requires the capitalization of
interest on debt that is allocable to property which has a long useful life,
208
 an estimated
                                               
205
  Sec. 163(e)(3)(B).  
206
  Pub. L. No. 98-369.  
207
  H.R. Conf. Rep. 98-861.
208
  Property has a long useful life for this purpose if such property is real property or is property with a
class life of 20 years or more (as determined under section 168) (sec. 263A(f)(4)(A)).   46
production period exceeding two years, or an estimated production period exceeding one year
and a cost exceeding $1 million.
209
By requiring that certain interest expense be capitalized, section 263A effectively defers
the deduction for interest paid until the related income is recognized.
Legislative Background
Section 263A was enacted by the Tax Reform Act of 1986.
210
  Congress believed that a
comprehensive set of rules governing the capitalization of costs of producing, acquiring, and
holding property, including interest expense, was advisable to reflect income more accurately,
and to alleviate distortions in the allocation of economic resources and the manner in which
certain activities are organized.
211
  The Technical and Miscellaneous Revenue Act of 1988
212
clarified the application of the interest allocation rule.
3. Interest in the case of straddles 
Present Law
A straddle generally refers to offsetting positions with respect to actively traded personal
property.
213
  Positions are offsetting if there is a substantial diminution in the risk of loss from
holding one or more other positions in personal property.
214
  
Section 263(g) requires taxpayers to capitalize certain otherwise deductible expenditures
allocable to personal property that is part of a straddle.  Thus, these expenditures effectively
reduce the gain or increase the loss recognized upon disposition of the property.  Expenditures
subject to this requirement are interest on indebtedness incurred or continued to carry property
(including any amount paid or incurred in connection with personal property used in a short sale)
as well as other amounts paid or incurred to carry the property, including insurance, storage or
transportation charges (“carrying charges”).  The amount of expenditures to be capitalized is
reduced by certain income amounts with respect to the personal property.
215
                                               
209
  Sec. 263A(f)(1)(B). 
210
  Pub. L. No. 99-514. 
211
  See Joint Committee on Taxation, General Explanation of the Tax Reform Act of 1986 (JCS-10-87),
May 4, 1987, pp. 508-509.
212
  Pub. L. No. 100-647.
213
  Secs. 1092(c)(1) and 1092(d)(1).
214
  Sec. 1092(c)(2). 
215
  Sec. 263(g)(2)(B)(i) - (iv).   47
Legislative Background
The limitation on deductibility of straddle interest and carrying charges (along with the
straddle rules more generally
216
) was enacted in 1981
217
 in response to the use of certain
straddles, which were executed with deductible financing and carrying charges, to defer ordinary
income and to convert it into long-term capital gain (referred to as “cash and carry” shelters). 
Such shelters typically involved the debt-financed purchase of a physical commodity, for
example silver, and an offsetting futures contract to deliver the silver in a subsequent taxable
year.  The taxpayer would deduct interest expense, storage and insurance costs in the first year,
offsetting ordinary investment income.  After 12 months, if the price of silver declined, the
taxpayer could deliver the silver to satisfy the futures contract, realizing a gain on the silver.  If
the price of silver had increased, the taxpayer could sell the silver, producing long-term capital
gain, and close out the short futures position, creating a short-term capital loss.  In either event,
the net gain on the two positions would approximately equal the carrying charges, but would be
reported as capital gain.  By requiring the capitalization of financing and carrying charges
Congress sought to discourage these transactions.
218
In 1984, the straddle rules were expanded to include exchange traded stock options in
response to transactions exploiting the exemption of stock and exchange-traded stock options
from the straddle rules.
 219
   For example, such transactions used offsetting deep-in-the-money
options on stock, the value of which could be expected to move in roughly opposite directions.
220
 
In 1986, section 263(g)(2) was amended to include in the definition of interest and
carrying charges any amount which is a payment with respect to a securities loan.
221
 
 In 2004 the straddle rules were broadened to include actively traded stock.  The same
legislation provided, among other things, that at the time a taxpayer acquires a straddle the
taxpayer is permitted to identify the straddle as an ‘identified straddle’ and thereby subject the
positions composing the straddle to a basis adjustment rule rather than to the general loss deferral
rule of section 1092(a)(1).
                                               
216
  Sec. 1092.  The straddle rules generally defer a loss on a position that is part of a straddle to the extent
the amount of the loss does not exceed the amount unrecognized gain on offsetting positions in the straddle.
217
  Economic Recovery Tax Act of 1981, Pub. L. No. 97-37.  
218
   See Joint Committee on Taxation, General Explanation of the Economic Recovery Tax Act of 1981
(JCS-71-81), December 29, 1981, pp. 292-293.
219
  Deficit Reduction Act of 1984, Pub. L. No. 98-369.  See also, Joint Committee on Taxation, General
Explanation of the Revenue Provisions of the Deficit Reduction Act of 1984 (JCS-41-84), December 31, 1984.   
220
  See, e.g., Joint Committee on Taxation, General Explanation of the Revenue Provisions of the Deficit
Reduction Act of 1984 (JCS-41-84), December 31, 1984, pp. 306-308.
221
  Tax Reform Act of 1986, Pub. L. No. 99-514.  48
G. Other Rules Relating to Business Debt and Equity
1. Employee Stock Ownership Plans
Present Law
In general
An employee stock ownership plan (“ESOP”) generally is a type of qualified retirement
plan that is designed to invest primarily in securities of the employer maintaining the plan.
222
  An
ESOP can be maintained by either a C corporation or an S corporation.  An employer
corporation may lend money to an ESOP, or the employer corporation may guarantee a loan
made by a third-party lender to the ESOP, to finance the ESOPs purchase of employer securities.
An ESOP that borrows funds to acquire employer securities generally is called a leveraged
ESOP.  In the case of an ESOP maintained by a C corporation, payments of principal on the
ESOP acquisition loan are deductible to the extent permitted under the general deduction limits
for contributions to qualified retirement plans (which generally limit the deduction for
contribution to a defined contribution plan for a year to 25 percent of the participants’
compensation),
223
 and interest payments are deductible without regard to the limitation. In
addition, dividends paid with respect the  employer stock of a C corporation held by an ESOP
that are passed through to participants or used to make acquisition loan payments generally may
also be deductible.
224
  This deduction is also allowed without regard to the general deduction
limits on contributions to qualified plans. There is also a nonrecognition provision for sales of C
corporation employer stock to an ESOP by a shareholder. 
Because an ESOP is a qualified retirement plan, the assets of an ESOP, including the employer
securities purchased with the loan are held in a tax-exempt trust.  For an S corporation
maintaining an ESOP, the trust of the ESOP is also exempt from UBIT.
225
  There are restrictions
                                               
222
  Under section 4975(e)(7), in order to be an ESOP (as opposed to another type of qualified retirement
plan), the plan must satisfy certain other requirements. The employer securities must be qualified employer
securities as defined in section 409(l) (which generally requires use of readily tradable securities, if available, or
common stock with the greatest voting power and dividend rights). The plan must satisfy the distribution and put
option requirements of section 409(h) and (o) (which generally require distributions be available in employer stock
for other than S corporation stock, and distributions of stock that is not readily tradable to be able to put to the
employer), the voting rights requirements of section 409(e) (which require that voting rights on shares held by the
ESOP be passed through to ESOP plan participants in certain circumstances), and the nonallocation requirements of
section 409(n) (which apply if the seller of stock to an ESOP claims nonrecognition treatment) and 409(p) (which 
apply in the case of ESOP maintained by an S corporation). The plan also must satisfy other requirements provided
in Treasury regulations. 
223
  Sec. 404(a)(9)(B). 
224
  Sec. 404(k). If the dividend is paid with respect to stock allocated to a participant’s accounts, the plan
must allocate employer securities with a fair market value of not less than the amount of such dividend to the
participant’s account for the year in which such dividend would have been allocated to such participant.
225
  Sec. 512(e)(3).   49
that limit the grant of stock options by an S corporation that maintains an ESOP but it is possible
in certain circumstances to grant options or warrants for S corporation stock that, when
combined with the outstanding shares of the S corporation, are options for up to 49 percent of the
stock.
226
Because an ESOP is a qualified retirement plan, it must satisfy the rules applicable to
qualified plans generally (that are designed to protect the interest of participants and limit the
amount of deferred compensation that is permitted in the plan) as well as a number of rules that
only apply to leveraged ESOPs (to protect the plan against fiduciary self-dealing and to ensure
that employees actually enjoy the benefits of stock ownership).  
Prohibited transaction exemption for ESOPs
Prohibited transaction rules
In order to prevent persons with a close relationship to a qualified retirement plan from
using that relationship to the detriment of plan participants and beneficiaries, the Code and
ERISA prohibit certain transactions between a qualified retirement plan and a disqualified
person.
227
 A disqualified person includes any fiduciary, a person providing services to the plan,
an employer any of whose employees are covered by the plan, an employee organization of
which any members are covered by the plan, and certain persons related to such disqualified
persons. Transactions prohibited between the plan and a disqualified person include among
others (1) the sale or exchange, or leasing of property; (2) the lending of money or other
extension of credit; and (3) the furnishing of goods, service, or facilities.  
Exemptions for leveraged ESOPs
Two statutory exemptions to the prohibited transaction rules permit the existence of
leveraged ESOPS.  First, qualified plans are allowed to acquire qualifying employer securities
for “adequate consideration.”
228
  Second, an ESOP (but not any other qualified retirement plan)
is permitted to borrow from the employer or other disqualified person, or the employer is
permitted to guarantee a loan to an ESOP by a third party lender, to acquire employer
securities.
229
  
To qualify for the loan exemption, the loan must be primarily for the benefit of
participants and beneficiaries of the plan. The loan must be for a specific term and the interest
                                               
226
  See the nonallocation rules under section 409(p) for the limits on stock options and other synthetic
equity, provided by an S corporation that maintains an ESOP, and section 4976A for the excise tax consequences. 
227
  Section 4975 of the Code and section 406 of ERISA. The Code imposes a two-tier excise tax on
prohibited transactions. The initial level tax is equal to 5 percent of the amount involved with respect to the
transaction.   
228
  Sec. 408(e) of ERISA and  section 4975(e)(13) of the Code..
229
  Sec. 408(b)(3) of ERISA and sec. 4975(d)(3) of the Code.  50
rate for the loan must not be in excess of a reasonable rate.
230
 Any collateral given to a
disqualified person by the plan in connection with the loan must consist only of qualifying
employer securities and generally only those acquired with the proceeds of the loan.
231
 The
shares are held in a suspense account under the plan but must be released and allocated to
participants as the loan is repaid under one of two specific methods provided in the
regulations.
232
  In the event of default on the loan, the value of plan assets transferred in
satisfaction of the loan must not exceed the amount of default.
233
 
In the case of a distribution of cash by an S corporation (as described in section 1368(a))
to a leveraged ESOP with respect to its stock, the ESOP is permitted to use distributions with
respect to unallocated shares held in the suspense account to make payments (principal and
interest) on the acquisition loan.
234
 Such use of the distribution is not a prohibited transaction and
will not cause the plan to violate the qualification requirements. 
Nonrecognition of gain for certain sales of stock to an ESOP   
A taxpayer selling certain qualifying employer securities to an ESOP may elect to defer
recognition of gain on the sale to the extent that the taxpayer reinvests the proceeds in qualified
replacement property within a replacement period.
235
 Gain is recognized upon the disposition of
the qualified replacement property, with the basis in employer securities carrying over to the
qualified replacement property.
236
 The only qualifying employer securities that are eligible for
this gain deferral are securities that are (1) issued by a domestic C corporation that, immediately
after the sale and for at least one year before the sale, has no readily tradable securities
outstanding,
237
 (2) have been held by the seller for more than one year, and (3) have not been
received by the seller as a distribution from a qualified plan or as a transfer pursuant to an option
or similar right to acquire stock granted to an employee by an employer (other than stock
acquired for full consideration). In order for the seller to be eligible for nonrecognition treatment,
the ESOP  must own, immediately after the sale, at least 30 percent of each class of outstanding
                                                
230
  Treas. Reg. sec. 54.4975-7(b)(7). 
231
  Treas. Reg. sec. 54.4975-7(b)(5).  
232
  Treas. Reg. sec. 54.4975-7(b)(8).
233
  Treas. Reg. sec. 54.4975-7(b)(6).
234
  Sec. 4975(f)(7). If the distribution is paid with respect to allocated stock purchased with the loan being
repaid and is used to repay the acquisition loan, the plan must allocate employer securities with a fair market value
of not less than the amount of such distribution to the participant for the year in which such distribution would have
been allocated to such participant.
235
  Sec. 1042(a) and (b)
236
  Sec. 1042(e).
237
  See Notice 2011-19, 2011-11 I.R.B.  550, for the definition of readily tradable securities. For the same
period, the domestic corporation that issued the employer securities must not be a member of a controlled group of
corporations that has readily tradable securities outstanding. 51
stock, or the total value of all outstanding stock of the corporation issuing the qualified
securities.
238
 
After purchasing the stock, in order for the plan to remain an ESOP, the plan must
preclude allocation of assets attributable to qualified securities to any taxpayer who makes an
election to defer gain on the sale for at least 10 years after the date if the sale of the qualified
securities to the plan or, if later, the date of the plan allocation attributable to the final payment of
the acquisition indebtedness for the securities.
239
  
Legislative Background
In general
The term “employee stock ownership plan” was added to the Code by the Employee
Retirement Income Security Act of 1974 (“ERISA”). However, prior to ERISA, stock bonus
plans could be structured to be the equivalent of a leveraged ESOP.
240
 
The Tax Reform Act of 1984
241
 and Tax Reform Act of 1986
242
 added most of  the
present law special deduction and nonrecognition of gain provisions with respect to leveraged
ESOPs. 
S corporations
Prior to 1998, trusts of retirement plan qualified under section 401(a) were not permitted
as shareholders of S corporations. Thus, prior to 1998, ESOPs could be maintained only by C
corporations. The Small Business Job Protection Act of 1996 (“SBJPA”) amended section 1361
to allow trusts qualified under section 401(a) to be S corporation shareholders. This change was
specifically intended to allow S corporations to maintain ESOPs.  Under SBJPA, the passthrough income from an S corporation to an ESOP as an S corporation shareholder was subject
to UBIT. The Taxpayer Relief Act of 1997 amended section 512(e) to provide an exemption
from UBIT  for the pass-through income from an S corporation to an ESOP with respect to the S
corporation shares held by the ESOP as qualified securities.
 243
   A qualified plan that is not an
                                               
238
  Subsequent to the sale, the ESOP  must hold the qualified securities for at least three years. An excise
tax applies for certain dispositions during that three- year period. 
239
  Sec.409(n). This limitation generally also applies to any other person who owns 25 percent of the stock
of the corporation. 
240
  Specifically a stock bonus plan, a type of retirement plan qualified under section 401(a), could be
structured as a plan invested primarily in employer securities acquired using funds borrowed by the plan.
241
  Pub. L. No.  98-369.
242
  Pub. L. No. 99-514.
243
  The exemption from UBIT treatment for an ESOP holding stock of an S corporation allowed an S
corporation with one employee (or a very small number of employees) to establish an ESOP and transfer all their
shares of S Corporation stock to the ESOP (possibly through a leveraged transaction that allowed the stock to be 52
ESOP continues to be subject to UBIT on the pass-through income on any shares of S
corporation stock held in the plan’s trust. The legislative history to the Taxpayer Relief Act of
1997
244
 gives as the reason for the ESOP exemption from UBIT that subjecting S corporation
ESOP income to UBIT is not appropriate because “such amounts would be subject to tax at the
ESOP level and also again when benefits are distributed to ESOP participants.”
245
The Economic Growth and Tax Reconciliation Act of 2001
246
 added section 409(p)
which placed some limitations on the concentration of stock ownership through the ESOP and
the use of synthetic equity, as defined in section 409(p)(6)(C) (which generally includes any
stock option, warrant, restricted stock, deferred issuance stock right or similar interest or right to
acquire or receive stock in the S corporation in the future, and certain other rights).  
2. Nonqualified preferred stock not treated as stock for certain purposes
Present Law
In general
Under section 351 of the Code, a transfer of property to a corporation in exchange solely
for stock of the transferee corporation is generally tax-free to each transferor.  Neither gain nor
loss is recognized with respect to the transferred property, provided that immediately after the
transfer the transferors, in the aggregate, are in control (as defined in section 368(c)) of the
corporation.
247
  
                                               
held in a suspense account until they could be allocated to the participant’s accounts).  This allowed the creation of a
tax-exempt S corporation with shares owned through the ESOP by a small number of individuals.  
244
  Pub. L. No. 105-34, Senate Report 105-033.
245
  When the stock is redeemed or sold to provide distributions from the plan to plan participants, the passthrough income may ultimately be subject to tax as ordinary income.  However, this may occur many years after the
income was earned by the S corporation, a deferral that can significantly reduce the present value of the tax. 
Furthermore, if the stock declines in value such that the value of all the income allocations to the ESOP is not
included in the amount distributed to plan participants, the S corporation income is never taxed to that extent.   
246
  Pub. L No. 107-16.
247
  Control for this purpose means ownership of stock possessing at least 80 percent of the total combined
voting power of all classes of stock entitled to vote and at least 80 percent of the total number of shares of all other
classes of stock of the corporation.  The IRS has ruled that “control” requires ownership of 80 percent of each class
of stock that is not entitled to vote (Rev. Rul. 59-259, 1959-2 C.B. 115).  Taxpayers may be able to construct stock
that has a higher percentage of the vote than of value (or vice versa) and retain (or fail to retain) the amount of each
class necessary to satisfy (or to fail to satisfy) this test in various circumstances.
The definition of control for this purpose is different from the definition for certain other purposes – for
example, for purposes of allowing a tax-free liquidation of a subsidiary corporation into a parent (sec. 332), or for
purposes of the rules treating certain transfers of stock between commonly controlled corporations as a contribution
of the stock followed by a redemption distribution that is generally treated as a dividend (sec. 304).   53
If, in addition to stock, the transferor receives other property (“boot”), such as money or
securities of the transferee corporation, then the transferor recognizes gain (but not loss) on the
transfer (to the extent of the value of the other property).
The transferor recognizes gain or loss on a transfer of property, however, if the transfer
fails to meet the requirements of the nonrecognition rules, for example, by failing the applicable
control requirement,
248
 or not receiving any stock in the exchange.  
Since 1997, the Code has required nonqualified preferred stock (“NQPS”) to be treated as
if it were not stock for some purposes but not others unless the Secretary of the Treasury so
prescribes.
249
  In particular, section 351(g) provides that NQPS is not stock for purposes of
section 351, with the result that NQPS received in an otherwise valid section 351 transaction is
taxable boot.
250
Definition of nonqualified preferred stock
Preferred stock is defined as stock which is limited and preferred as to dividends and
does not participate in corporate growth to any significant extent.
251
  Preferred stock is generally
“nonqualified preferred stock” if (1) the holder has the right to require the issuer or a related
person to redeem or purchase the stock within the 20-year period beginning on the issue date of
the stock, and such right or obligation is not subject to a contingency which, as of the issue date,
makes remote the likelihood of the redemption or purchase; (2) the issuer or a related person is
required to redeem or purchase the stock within such 20-year period and such right or obligation
is not subject to a contingency which as of the issue date makes remote the likelihood of
redemption or repurchase; (3) the issuer or a related person has the right to redeem or purchase
the stock within such 20-year period and, as of the issue date, it is more likely than not that such
right will be exercised; or (4) the dividend rate on such stock varies in whole or in part (directly
or indirectly) with reference to interest rates, commodity prices, or other similar indices.
252
 
A right or obligation will not cause preferred stock to be NQPS, however, if (1) the stock
relinquished or received is not in a corporation any of whose stock is, or is to become, publicly
                                               
248
  Certain prearranged dispositions of stock that would cause a failure of the control requirement may
cause a transaction not to be within the scope of section 351, so that loss or gain on the transferred property is
recognized.  See, e.g., Rev. Rul. 54-96, 1954-1 C.B. 111 (prearranged plan caused loss of control); Intermountain
Lumber Co. v. Commissioner, 65 T.C. 1025 (1976) (finding incorporator lacked requisite control under section 351
where, as part of the incorporation, he irrevocably contracted to sell 50 percent of the stock received).
249
  The Secretary of the Treasury has regulatory authority to prescribe the treatment of NQPS for any other
purpose of the Code.  The regulatory authority has never been exercised.
250
  For a discussion of certain incentives to use nonqualified preferred stock, and consideration of other
aspects of present law taxpayers may use to accomplish similar results, see Joint Committee on Taxation,
Description of Revenue Provisions Contained in the President’s Fiscal Year 2012 Budget Proposal (JCS-3-11), June
2011, pp. 385-394. 
251
  Sec. 351(g)(3)(A). 
252
  Sec. 351(g)(2)(A) and (B).   54
traded, and the right or obligation may be exercised only upon the death, disability, or mental
incompetency of the holder, or (2) in the case of a right or obligation to redeem or purchase stock
transferred in connection with the performance of services for the issuer or a related person (and
which represents reasonable compensation), it may be exercised only upon the holder’s
separation from service from the issuer or a related person.
253
  
Other consequences of nonqualified preferred stock
In addition to the rules dealing with transfers to a controlled corporation, other corporate
tax rules also permit certain reorganizations, divisions, and recapitalizations of corporations to be
accomplished without tax to the exchanging shareholders or the corporations involved, provided
that certain requirements are met and only to the extent that certain permitted property is
received.  Under these rules, NQPS that is exchanged or received with respect to stock other than
NQPS is generally not treated as permitted property (with an exception for certain
recapitalizations of family-owned corporations) so that gain (but not loss) is generally recognized
on certain exchanges of stock in one corporation for NQPS in another, where the basic
requirements of a qualifying transaction are otherwise met.  However, except as provided in
regulations, unlike the case of the section 351 transaction, the NQPS is treated as stock for
purposes of determining whether a transaction qualifies as a tax-free reorganization or division
(apart from the rules for determining the extent of taxable boot received in such a transaction).
254
   
Legislative Background
Section 351(g) was enacted by the Tax Relief Act of 1997.
255
  The legislative history
states that the Congressional concern leading to the adoption of the rules was that “certain
preferred stocks have been widely used in corporate transactions to afford taxpayers nonrecognition treatment, even though the taxpayer may receive relatively secure instruments in
exchange for relatively risky instruments.”
256
 
In 2004, the statute was amended to add a statement that stock shall not be treated as so
participating unless there is “a real and meaningful likelihood” of the shareholder actually
participating in the earnings and growth of the corporation.”
257
  The change was made in
response to Congressional concern that taxpayers might attempt to avoid the characterization of
                                                
253
  Sec. 351(g)(2)(C). 
254
  Secs. 354(b)(2)(C), 355(a)(3)(D), and 356(e). 
255
  Pub. L. No. 105-34.
256
  H.R. Rep. No. 105-148, June 24, 1997, p. 472; S. Rep. No. 105-33, June 20, 1997, p. 150.  See, also,
Martin D. Ginsburg and Jack S. Levin, Mergers, Acquisitions, and Buyouts (August 2010), ¶ 902.1 et seq., giving an
example of a similar transaction that could have been impacted by the 1997 legislation.  That example is based on
the facts of the acquisition of National Starch & Chemical Corp. detailed in National Starch & Chemical Corp. v.
Commissioner, 93 T.C. 67 (1978) aff’d, 918 F.2d 426 (3
rd
 Cir. 1990) which refers to a private letter ruling dated
June 28, 1978 (described by Ginsburg and Levin as PLR 7839060 (June 28, 1978)).     
257
  Pub. L. No. 108-357, sec. 899(a), amending section 351(g)(3).  55
an instrument as NQPS by including illusory participation rights or including terms that
taxpayers could argue create an “unlimited” dividend.
258
  In 2005, the statute was amended
again, to provide that “if there is not a real and meaningful likelihood that dividends beyond any
limitation or preference will actually be paid, the possibility of such payments will be
disregarded in determining whether stock is limited and preferred as to dividends.”
                                           
                      
259
  Pub. L. No. 109-135, sec. 403(kk), amending section 351(g)(3).  56
II. DATA WITH RESPECT TO BUSINESS DEBT
The following tables show selected data related to business debt, equity, and interest
expense.  
Table 2 provides an overall picture of the growth of non-financial corporate, household,
and federal debt as a share of Gross National Product (“GNP”) from 1987 to 2010.  Nonfinancial corporate debt has grown more modestly than either household debt or Federal debt. 
Non-financial corporate debt as a share of GNP has grown about 13 percent since 1987, while
household debt and Federal debt have each grown by more than 50 p   

259
  Pub. L. No. 109-135, sec. 403(kk), amending section 351(g)(3).  56
II. DATA WITH RESPECT TO BUSINESS DEBT
The following tables show selected data related to business debt, equity, and interest
expense.  
Table 2 provides an overall picture of the growth of non-financial corporate, household,
and federal debt as a share of Gross National Product (“

II. DATA WITH RESPECT TO BUSINESS DEBT
The following tables show selected data related to business debt, equity, and interest
expense.  
Table 2 provides an overall picture of the growth of non-financial corporate, household,
and federal debt as a share of Gross National Product (“GNP”) from 1987 to 2010.  Nonfinancial corporate debt has grown more modestly than either household debt or Federal debt. 
Non-financial corporate debt as a share of GNP has grown about 13 percent since 1987, while
household debt and Federal debt have each grown by more than 50 percent.  
Table 3 shows the distribution of holdings of corporate equity and bonds by type of
holder for the years 1990, 2000, and 2010.  Over that 20-year period, the share of corporate
equities held directly by the household sector has declined significantly while that held by
mutual funds has risen significantly. Because most mutual fund shares are owned by the
household sector, there appears to be little change in the combined share of corporate equities
owned directly by the household sector or through mutual funds.    The share of corporate
equities held by insurance and pension funds has declined while that of foreign investors has
risen substantially.  
Over the same 20-year period, the share of corporate bonds held by the household and
mutual fund sectors considered together has risen 62 percent, while the share of corporate bonds
held by foreign investors has nearly doubled. The share of corporate bonds held by insurance and
pension funds has declined by about 50 percent, from over 55 percent in 1990 to under 28
percent in 2010.  The other notable change is the share of corporate bonds held by government
sponsored enterprises and funding corporations, including financial stabilization programs, from
zero percent of holdings in 1990 to 9.3 percent in 2010.
Table 4 shows debt-to-equity and debt to net worth ratios of nonfinancial C corporations
and S corporations (excluding farms) from 1987 to 2010.  For the former series, equity is
measured as the market value of equities outstanding.  For the latter, net worth is measured as
total assets minus liabilities, with nonfinancial assets measured at market value in the case of real
estate and at replacement cost in the case of inventories and equipment and software.  The
former series generally shows more volatility owing to its reliance on the market value measure
of outstanding equities.  The latter series shows that the debt-to-net-worth of nonfinancial
corporations has been relatively stable over the 24-year period.
Table 5 shows interest expense and taxable income of nonfinancial corporations from
1987 to 2008 as reported on corporate income tax returns, from 1987 to 2008.  The table also
shows the interest expense as a percentage of taxable income before interest expense.  Though
interest expense fluctuates with the level of debt and interest rates, this percentage appears to
primarily reflect the effects of the business cycle, as the percentage has peaks in 1990 and 2001,
when taxable income declined.  In addition to business cycle effects, other changes in tax policy
that have an impact on taxable income affect this percentage. For example, bonus depreciation
enacted in 2010 would lower otherwise reported taxable income in 2010, 2011 and 2012, and
potentially increase otherwise reported taxable income in later years. 57
Table 6 shows interest and net income for corporations, S corporations, and partnerships
from 1991 to 2008, and also shows the interest expense as a percentage of net income before
interest expense.   These data reflect similar business cycle effects as noted above, as well as
showing a significant downward trend for S corporations in interest expense as a percentage of
net income before interest expense.  Table 6 also shows that C corporations’ interest expense, in
the aggregate and as a percentage of net income before interest expense, exceeds the comparable
figures for partnerships and S corporations throughout this period.  These data reflect the larger
size of the C corporate sector, but C corporations may also have a Federal income tax incentive
to incur debt, as interest is deductible in determining the corporate tax.  By contrast, partnerships
and S corporations are not subject to an entity-level tax.
Table 6 illustrates that partnership interest expense, in the aggregate and as a percentage
of net income before interest expense, has exceeded S corporation interest since 1999.   Among
other factors, these differences may reflect the difference in tax rules for determining basis of
partners’ and S corporation shareholders’ equity interests, respectively.
Lastly, Table 7 shows data for interest expense and net income for all corporations,
separated into those with annual business receipts either above or below five million dollars. 
The data on interest expense as a percentage of net income before interest expense again appear
to reflect business cycle effects of the 2000-2001 economic slowdown, regardless of the size of
corporations. 
   58


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