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Originally Posted by buddyhu
One way to lessen the pain would be to sell some stock that has decreased in value (if you own some outside of a retirement account). The capital losses from selling any losers can offset the capital gain on the stock buyback. You might also investigate whether you can donate to a charity some of the stock that was granted to you before the company does the buyback; if so, you would get the full value of the stock as a donation and would not pay capital gains on any stock that is donated.
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I don't think in this circumstances the OP is in control of the sale. It sounds like it is one stock and it is connected to a corporate buy out. My wife had this same thing. She worked for a high tech company that got bought out. She had received stocks as a stock option and the new company bought them back during the buy out. As I remember, the stocks were worth less at the time of the buy out than they were when they were issued and we took a loss on them on our taxes, which at the time worked out quite well for us.