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Short sales against the box after the TRA '97.

Prior to the enactment of the Taxpayer Relief Act of 1997 (TRA TRA Training
TRA Transfer
TRA Transition
TRA Tennessee Regulatory Authority
TRA Telecommunications Regulatory Authority (Oman)
TRA Tax Reform Act (1976, 1984, or 1986)
TRA Teachers Retirement Association
 '97), a taxpayer could hedge against volatility in the value of stock by completing a "short sale against the box," which had no tax consequences until the taxpayer closed the position by returning borrowed shares to the lender. The TRA '97 curtailed use of this technique by deeming the short sale a constructive sale on which gain or loss must be immediately recognized (whether or not the position is sold). This article explains the new law and whether the short sale against the box has survived.

The legislative history and the conference reports for the Taxpayer Relief Act of 1997 (TRA '97) clearly indicate a congressional desire to diminish tax-motivated transactions, such as shorting against the box. In a "short sale against the box," a taxpayer owns a long position and borrows an equal amount of stock from his broker to sell. The taxpayer believes that the stock price will drop in the near future and that the short position can be covered with less expensive shares.

Before the TRA '97, a short sale against the box transaction generally was used to defer de·fer 1  
v. de·ferred, de·fer·ring, de·fers
1. To put off; postpone.

2. To postpone the induction of (one eligible for the military draft).

 capital gains tax on the disposition of a long position. A taxpayer with a significantly appreciated long position would hedge it by selling an equal amount of stock short. The taxpayer would then hold the hedged position until a future tax year, and eventually cover it with the low-basis long position. However, the TRA '97 significantly curtailed the usefulness of this deferral deferral - Waiting for quiet on the Ethernet.  technique; this article discusses these changes and offers planning options.


Prior to the TRA '97, a taxpayer generally did not recognize immediate gain on a short sale against the box. The gain on the borrowed and sold shares was not recognized until the taxpayer closed the sale by returning identical property to the lender. Sec. 1259 was enacted by TRA '97 Section 1001(a). Post-TRA '97 Sec. 1259(a) (1) is relatively straightforward--if a taxpayer makes a "constructive sale" of an "appreciated financial position" (AFP (1) (AppleTalk Filing Protocol) The file sharing protocol used in an AppleTalk network. In order for non-Apple networks to access data in an AppleShare server, their protocols must translate into the AFP language. See file sharing protocol. ), he recognizes gain as if such position were actually sold, assigned as·sign  
tr.v. as·signed, as·sign·ing, as·signs
1. To set apart for a particular purpose; designate: assigned a day for the inspection.

 or otherwise terminated at its fair market value (FMV FMV - full-motion video ) on the date of such constructive sale. In addition, under Sec. 1259(a)(2), a proper adjustment is made in the amount of any gain or loss subsequently taken into account on that position and a new holding period begins for that position starting on the date of the constructive sale.


Sec. 1259(b)(1) defines an AFP generally as any position with respect to stock, a debt instrument or partnership interest if there would be gain on a taxable disposition of the position at its FMV. Other debt instruments, including those identified as part of a hedging or straddle In the stock and commodity markets, a strategy in options contracts consisting of an equal number of put options and call options on the same underlying share, index, or commodity future.  transaction, are also AFPs. Sec. 1259(b)(3) defines a "position" as an interest, including a futures or forward contract, short sale or option. The constructive sale rules are designed to prevent a taxpayer from entering into long-term Long-term

Three or more years. In the context of accounting, more than 1 year.


1. Of or relating to a gain or loss in the value of a security that has been held over a specific length of time. Compare short-term.
 hedging transactions that would defer gain indefinitely in·def·i·nite  
Not definite, especially:
a. Unclear; vague.

b. Lacking precise limits: an indefinite leave of absence.

 while substantially reducing or eliminating the risk of loss.

Constructive Sale

According to according to
1. As stated or indicated by; on the authority of: according to historians.

2. In keeping with: according to instructions.

 Sec. 1259(c)(1), a taxpayer has made a constructive sale of an AFP when he does any of the following:

* Enters into a short sale of the same or substantially identical property.

* Enters into an offsetting notional principal contract The examples and perspective in this article or section may not represent a worldwide view of the subject.
Please [ improve this article] or discuss the issue on the talk page.
 with respect to the same or substantially identical property.

* Enters into a futures or forward contract to deliver the same or substantially identical property.

* In the case of an AFP that is a short sale, offsetting notional principal contract or futures or forward contract as to any property, acquires the same or substantially identical property.

* To the extent provided in regulations, enters into one or more other transactions (or acquires one or more positions) that have substantially the same effect as a transaction described above.

The Senate Committee Report1 noted that, if the standard for a constructive sale is met for only a pro rata [Latin, Proportionately.] A phrase that describes a division made according to a certain rate, percentage, or share.

In a Bankruptcy case, when the debtor is insolvent, creditors generally agree to accept a pro rata share of what is owed to them.
 portion of the taxpayer's AFP, that portion will be treated as constructively sold. Constructive sale determination for pro rata positions is determined by the actual sales method after adjusting for previous constructive sales.

It is anticipated that Treasury will use the authority granted under Sec. 1259(c)(1)(E) to treat as constructive sales other financial transactions that, like those specified in the provision, have the effect of eliminating substantially all of the taxpayer's risk of loss and opportunity for income or gain on the AFP. It is also anticipated that regulations, when issued, will provide specific standards for determining whether several common transactions will be treated as constructive sales. Sec. 1259(c)(1) specifies certain transactions that Congress will treat as constructive sales and leaves other transactions (most notably, those involving options) for Treasury to address in regulations. Presently, only those transactions enumerated This term is often used in law as equivalent to mentioned specifically, designated, or expressly named or granted; as in speaking of enumerated governmental powers, items of property, or articles in a tariff schedule.  in Sec. 1259(c)(1) are constructive sales until regulations provide otherwise.

Treasury's authority to treat additional transactions as constructive sales is not limited to transactions in substantially identical property. The Conference Committee Report(2) made it clear that Congress expects Treasury to provide specific standards for determining whether several common transactions (e.g., collars and in-the-money options In-the-money option

An option that has value.
) will result in constructive sales. Treasury is also directed to establish "safe harbor Safe Harbor

1. A legal provision to reduce or eliminate liability as long as good faith is demonstrated.

2. A form of shark repellent implemented by a target company acquiring a business that is so poorly regulated that the target itself is less attractive.
" rules that can be applied without reference to option prices or predictions of future volatility for these and other transactions that do not result in constructive sale treatment. Sec. 1259(f) grants Treasury broad, general authority to issue regulations.


According to Sec. 1259(c)(3), the constructive sale rule does not apply to certain short-term Short-term

Any investments with a maturity of one year or less.


1. Of or relating to a gain or loss on the value of an asset that has been held less than a specified period of time.
 hedges. These include (1) any transaction closed before the end of the 30th day after the close of the tax year (short-term hedge rule), if (2) the taxpayer holds the AFP to which the transaction relates (i.e., securities, if the transaction is a short sale against the box) throughout the 60-day period beginning on the date the transaction is closed and (3) at no time during the 60-day period does the taxpayer reduce his risk of loss on the AFP (i.e., the appreciated stock) or substantially similar property (the 60-day rule).

The restriction against hedging during the 60-day period is an attempt to make that holding period meaningful and to prevent a taxpayer from obtaining a multiple-year deferral by stringing together a series of short-term hedges.

Example: T owns 1,000 shares of ABC ABC
 in full American Broadcasting Co.

Major U.S. television network. It began when the expanding national radio network NBC split into the separate Red and Blue networks in 1928.
 stock that he purchased in 1995. On Jan. 1, 1998, T sells short 1,000 shares of ABC. The position was closed on Jan. 15, 1999, with ABC shares purchased on that date. The 1,000 shares of ABC purchased in 1995 are sold on July July: see month.  1, 1999. No constructive sale of ABC occurs in 1998, because the short-term hedge rule is satisfied. The rule is satisfied because (1) the short position was closed within 30 days after the end of 1998; and (2) the 60-day requirement was not violated vi·o·late  
tr.v. vi·o·lat·ed, vi·o·lat·ing, vi·o·lates
1. To break or disregard (a law or promise, for example).

2. To assault (a person) sexually.

, because the long position remained open for 60 days after Jan. 15, 1999 (the date on which the short position was closed) and the long position remained unhedged during that time. The character of the gain or loss realized on the July 1, 1999 sale of the long position would be long-term, because the short sale against the box was not deemed to be a constructive sale and the ABC stock had a long-term holding period when the short sale was entered into.

Had T closed the short position using the 1,000 shares purchased in 1995 rather than the newly purchased shares, or had T established a second short position as to the ABC stock before March 16, 1999, the 60-day requirement would not have been met; a constructive sale would have occurred on Jan. 1, 1998. In addition, a constructive sale of T's 1,000 ABC shares would have occurred on Jan. 1, 1998 if the short position had been closed on Feb. 1, 1999, because the short-term hedge rule would have been violated. Had a constructive sale occurred, the long-position's holding period would have been "clipped clip 1  
v. clipped, clip·ping, clips
1. To cut, cut off, or cut out with or as if with shears: clip coupons; clipped three seconds off the record.
" and restarted. Thus, even though the long position was originally purchased in 1995, the constructive sale would treat the long position as being purchased on Jan. 1, 1998.

The constructive sale provision is effective for constructive sales entered into after June June: see month.  8, 1997. A special rule was provided in TRA '97 Section 1001 (d)(2) for transactions before that date that would have been constructive sales under Sec. 1259. The positions in such a transaction will not be taken into account in determining whether a constructive sale after June 8, 1997 has occurred, provided that the taxpayer identifies the offsetting positions of the earlier transaction within 30 days after Aug. 5, 1997 (the TRA '97 enactment date). The special rule will cease to apply on the date the taxpayer no longer holds any of the offsetting positions so identified.


It is still possible to do a short sale against the box and avoid constructive sale treatment if the taxpayer meets the clearly enumerated exceptions of closing within 30 days after the end of the tax year and holding the remaining long position unhedged for 60 days. Even though this is still possible, from an economic perspective, short sales against the box designed to avoid constructive sale treatment have now become risky transactions.

To fully recognize the potentially negative impact of a short sale against the box after TRA '97, it is important to understand that the taxpayer can no longer use previously owned shares (i.e., the underlying long position) to close out the short sale against the box position. It is impossible to satisfy one prong of the Sec. 1259(c)(3)(A) exception (closing before the 30th day following the end of the tax year) while satisfying the 60-day holding period if the underlying long position is used to close the short sale.

Further, taxpayers may be surprised by the tax results generated by a short sale against the box designed to avoid constructive sale treatment. For example, if the market price of the stock sold short declines, the taxpayer potentially has a smaller amount of long-term gain Long-term gain

A profit on the sale of a capital assets held longer than 12 months, and eligible for long-term capital gains tax treatment.
 in the underlying long position, but he will realize short-term capital gain Short-term capital gain

A profit on the sale of a security or mutual fund share that has been held for one year or less. A short-term capital gain is taxed as ordinary income.
 when the short position is closed. If the stock price rises, the taxpayer potentially has more long-term gain in the long position, and realizes either long-term or short-term capital loss when the short position is closed, depending on how long he owned the long position when the short sale was executed.(3)


As a result of new Sec. 1259, short sales against the box designed to avoid constructive sale treatment have become risky transactions.4 Even though one can still do a short sale against the box after the TRA '97 without triggering a constructive sale, it often will not make economic sense to do so. Because a taxpayer cannot use his underlying long position as replacement shares, and a constructive sale restarts the taxpayer's holding period in the long position, short sales against the box expose the taxpayer to market risk and may subject him to short-term capital gains rates.


* In a short sale against the box, a taxpayer holding a long position borrows and sells shares identical to that position, then subsequently gives the long position shares to the lender to close the transaction.

* Generally under new Sec. 1259, a short sale against the box is a constructive sale on which gain or loss must be immediately recognized, unless strict rules are met.

* Sec. 1259 is designed to prevent a taxpayer from entering into long-term hedging transactions that would defer gain indefinitely while substantially reducing or eliminating the risk of loss.

For more information about this article, contact Mr. Tucker at (202) 467-3875 or letucker or Mr. Watson at (202) 467-2433 or mwatson@

(1) S. Rep't No. 105-33, 105th Cong n. 1. (Med.) An abbreviation of Congius. ., 1st Sess. (1997), p. 124.

(2) H. Rep't No. 105-220, 105th Cong., 1st Sess. (1997), p. 513.

(3) See Sec. 1233(d).

(4) However, it is possible to separate the long position into multiple blocks (e.g., blocks A, B and C), short one block (i.e., block A) and use another block (i.e., block B) to close the short position, under Sec. 1259(e)(3); nonetheless, a short sale against the box is no longer a perfect hedge Perfect hedge

A situation in which the profit and loss from the underlying asset and the hedge position are equal.

perfect hedge

A hedge that exactly offsets any gains or losses from an existing investment position.

Lawrence Lawrence.

1 City (1990 pop. 26,763), Marion co., central Ind., a residential suburb of Indianapolis, on the West Fork of the White River. It has light manufacturing.

2 City (1990 pop. 65,608), seat of Douglas co., NE Kans.
 E. Tucker, J.D., MBA MBA
Master of Business Administration

Noun 1. MBA - a master's degree in business
Master in Business, Master in Business Administration
 Manager Washington National Tax KPMG LLP LLP - Lower Layer Protocol  Washington, DC

Mark T. Watson, CPA/PFS, CFP 1. CFP - Constraint Functional Programming.
2. CFP - Communicating Functional Processes.
3. CFP - Call For Papers (for a conference).
 Partner Washington National Tax KPMG LLP Washington, DC
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Title Annotation:taxation of hedge stock transactions
Author:Watson, Mark T.
Publication:The Tax Adviser
Geographic Code:1USA
Date:Apr 1, 1999
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