I have apple stock I bought long ago. This year I wrote call options on it. My plan was to hedge some of the risk. If the stock went up I would cover the options, claim short term loss on the options and keep long term capital gains on the stock.
My first question is, is that a legitimate tax strategy? Short term capital loss on the options one year, long term gains on the stock another year?
But, my plan didn't work out. To my surprise the options where assigned and now I have large long term capital gains this year I don't want. Is there any options to rebuy the stock to pay tax another year?
Your strategy is quite legitimate.
If your call options are exercised and you sold the stocks, you'll have to pay taxes on the long-term capital gains. Even if you rebougth the same stocks, your sale will still be taxed.
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