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Subject:   ISO wash sale
Date:   Thu, 19 Jul 2001
From:   Anonymous

Hello Mike!

Great website, am also on your mailing list..

I have paid my 2000 taxes which include a large ISO wash sale component. There is also a significant AMT component but I'm okay with it as I knowingly held on to the positions at year end.

What are the chances of now writing to the IRS that the wash sale was a mistake and (1) common understanding on the topic was mistaken (NYT, WSJ articles), (2) there was no way to recover from the error (unlike regular wash sales or AMT exercises)

And arguing for a one-time permission to not report the wash sale related bargain element as ordinary income??

Thanks,
Anonymous

Answer

Date:   Wed, 25 Jul 2001

Hello,

I’m sorry, but there is no provision for claiming a wash sale was a "mistake."

The New York Times and Wall Street Journal are not substantial authority in the Tax Court.

If you sold the replacement shares before the end of the year, you could take the aggressive position that the attributes of the ISO shares attach to the replacement shares, so the escape hatch should apply. This is a long shot for which there isn’t much authority.

My condolences,

Good luck!

Mike Gray

For more information about incentive stock options, request our free report, Incentive Stock Options - Executive Tax and Financial Planning Strategies.

IRS Circular 230 Disclosure: As required by U.S. Treasury Regulations, you are hereby advised that any written tax advice contained in this answer was not written or intended to be used (and cannot be used) by any taxpayer for the purpose of avoiding penalties that may be imposed under the U.S. Internal Revenue Code.