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Subject:   Sale of Stock Option rights
Date:   Wed, 27 Apr 2005
From:   George

Mr. Gray

I am about to be forced to exercise NQSOs with immediate sale of the stock in a cashless transaction due to a company sale. The ordinary income will be substantial. If I sell the option rights (the option) back to the company or a majority shareholder of my company just prior to the company sale, will I be able to report a long-term capital gain? I have had the options for more than one year. Also, will this avoid the AMT?

Regards
George

Answer

Hello George,

Non-qualified stock options are not capital assets. Since they are "loaded" with ordinary income, ordinary income is reported when you (the employee, service provider, transferee spouse or beneficiary) sell them. There is no adjustment for AMT for the exercise of a non-qualified option like for ISOs, because the same income is reported for regular tax and AMT.

Good luck!

Mike Gray

For more information about non-qualified stock options, request our free report, Non-Qualified 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.