Constructive Sales Of Appreciated Financial Positions

In the past, many taxpayers have delayed recognition of income on securities or other properties by hedging their position to offset the risk of continually holding their position. Often, the gain is delayed so that the lower long-term capital gains rate would apply to the sale rather than the short-term ordinary income tax rate that would apply for short-term gains. To prevent this delay of income recognition, the tax law treats any hedging transaction of an appreciated financial position as a constructive sale.

Example: How Hedging a Position May Cause a Constructive Sale

An appreciated financial position is the ownership of stock, options, debt instruments, partnership interests, and interests in certain publicly traded trusts, that would result in a gain if the position was sold.

However, an appreciated financial position does not include any instruments which would otherwise already be subject to tax, such as futures contracts that are subject to mark-to-market rules, or where there is little risk to the taxpayer in holding the position, such as holding debt instruments or interests in publicly traded trusts that qualifies for the debt exception:

There are 4 basic types of transactions that are subject to the constructive sale rules:

  1. short sales,
  2. notional principal contracts (these contracts are designed for tax avoidance and do not seem to have true economic worth),
  3. forward or futures contracts that are not marked to market, or
  4. the purchase of a long position to cover a short position [IRC §1259 (c)].

Constructive sale rules do not apply to contracts, with terms of 1 year or less, that are not publicly traded, if they conform to the following safe harbor requirements:

Because exchange traded futures contracts — what the tax code refers to as Section 1256 contracts — are marked-to-market daily, gain or loss must be realized by the end of the year even if the taxpayer continues to hold the contract. Since futures contracts are taxed annually, the taxpayer cannot save on taxes by delaying its sale, so the constructive sale rules are unnecessary. The IRS gets its money, regardless.

Once a given position is treated as a constructive sale, then constructive sales rules will not apply to the same position as long as the position is held.

Example: Constructive Sale Rules Apply to the Same Position Only Once

Because you continued to hold the original position, your 2nd short sale is not recognized as a constructive sale, so it does not have to be reported until it is closed out and any gain on the original stock does not have to be reported until the stock is actually sold.

However, if you hold another appreciated position and sell the original position before closing out the short sale, then constructive sale rules may apply to the other position.

Example: Constructive Sale Rules May Apply to Different Related Positions

Tax Objective of Constructive Sale Rules

The purpose of the constructive sale rules is the same as the purpose for wash sale rules and the rules governing the taxation of short sales: to prevent taxpayers from trying to convert long-term losses into short-term losses or short-term gains into long-term gains by taking advantage of tax loopholes. The constructive sale rules do not change ultimate profits — they only change when the profits have to be reported and they also change the tax basis of the securities and their holding periods.

The constructive sale rules do not allow any losses, since they only apply to appreciated financial positions, which, by definition, applies only to gains. So if you buy stock for $16 a share, then later sell short the same stock for $15 a share, then the constructive sale rules do not apply, since it is not an appreciated financial position.