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IRS.gov Website
Publication 550
taxmap/pubs/p550-025.htm#en_us_publink100010462

Related Party Transactions(p50)

rule
Special rules apply to the sale or trade of property between related parties.
taxmap/pubs/p550-025.htm#en_us_publink100010463

Gain on Sale or Trade
of Depreciable Property(p50)

rule
Your gain from the sale or trade of property to a related party may be ordinary income, rather than capital gain, if the property can be depreciated by the party receiving it. See chapter 3 in Publication 544 for more information.
taxmap/pubs/p550-025.htm#en_us_publink100010464

Like-Kind Exchanges(p50)

rule
Generally, if you trade business or investment property for other business or investment property of a like kind, no gain or loss is recognized. See Like-Kind Exchanges, earlier, under Nontaxable Trades.
This rule also applies to trades of property between related parties, defined next under Losses on Sales or Trades of Property. However, if either you or the related party disposes of the like property within 2 years after the trade, you both must report any gain or loss not recognized on the original trade on your return for the year in which the later disposition occurs.
This rule generally does not apply to:
If a property holder's risk of loss on the property is substantially diminished during any period, that period is not counted in determining whether the property was disposed of within 2 years. The property holder's risk of loss is substantially diminished by:
taxmap/pubs/p550-025.htm#en_us_publink100010465

Losses on Sales or
Trades of Property(p51)

rule
You cannot deduct a loss on the sale or trade of property, other than a distribution in complete liquidation of a corporation, if the transaction is directly or indirectly between you and the following related parties.
In addition, a loss on the sale or trade of property is not deductible if the transaction is directly or indirectly between the following related parties.
taxmap/pubs/p550-025.htm#en_us_publink100010466

Multiple property sales or trades.(p51)

rule
If you sell or trade to a related party a number of blocks of stock or pieces of property in a lump sum, you must figure the gain or loss separately for each block of stock or piece of property. The gain on each item may be taxable. However, you cannot deduct the loss on any item. Also, you cannot reduce gains from the sales of any of these items by losses on the sales of any of the other items.
taxmap/pubs/p550-025.htm#en_us_publink100010467

Indirect transactions.(p51)

rule
You cannot deduct your loss on the sale of stock through your broker if, under a prearranged plan, a related party buys the same stock you had owned. This does not apply to a trade between related parties through an exchange that is purely coincidental and is not prearranged.
taxmap/pubs/p550-025.htm#en_us_publink100010468

Constructive ownership of stock.(p51)

rule
In determining whether a person directly or indirectly owns any of the outstanding stock of a corporation, the following rules apply.
taxmap/pubs/p550-025.htm#en_us_publink100010469
Rule 1.(p51)
Stock directly or indirectly owned by or for a corporation, partnership, estate, or trust is considered owned proportionately by or for its shareholders, partners, or beneficiaries.
taxmap/pubs/p550-025.htm#en_us_publink100010470
Rule 2.(p51)
An individual is considered to own the stock directly or indirectly owned by or for his or her family. Family includes only brothers and sisters, half-brothers and half-sisters, spouse, ancestors, and lineal descendants.
taxmap/pubs/p550-025.htm#en_us_publink100010471
Rule 3.(p51)
An individual owning, other than by applying rule 2, any stock in a corporation is considered to own the stock directly or indirectly owned by or for his or her partner.
taxmap/pubs/p550-025.htm#en_us_publink100010472
Rule 4.(p51)
When applying rule 1, 2, or 3, stock constructively owned by a person under rule 1 is treated as actually owned by that person. But stock constructively owned by an individual under rule 2 or rule 3 is not treated as owned by that individual for again applying either rule 2 or rule 3 to make another person the constructive owner of the stock.
taxmap/pubs/p550-025.htm#en_us_publink100010473

Property received from a related party.(p51)

rule
If you sell or trade at a gain property you acquired from a related party, you recognize the gain only to the extent that it is more than the loss previously disallowed to the related party. This rule applies only if you are the original transferee and you acquired the property by purchase or exchange. This rule does not apply if the related party's loss was disallowed because of the wash sale rules, described later under Wash Sales.
If you sell or trade at a loss property you acquired from a related party, you cannot recognize the loss that was not allowed to the related party.
taxmap/pubs/p550-025.htm#en_us_publink100010474

Example 1.(p51)

Your brother sells you stock for $7,600. His cost basis is $10,000. Your brother cannot deduct the loss of $2,400. Later, you sell the same stock to an unrelated party for $10,500, realizing a gain of $2,900. Your reportable gain is $500 (the $2,900 gain minus the $2,400 loss not allowed to your brother).
taxmap/pubs/p550-025.htm#en_us_publink100010475

Example 2.(p51)

If, in Example 1, you sold the stock for $6,900 instead of $10,500, your recognized loss is only $700 (your $7,600 basis minus $6,900). You cannot deduct the loss that was not allowed to your brother.