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I have 800 shares of a stock held for several years. Cost basis is zero due to splits and previous sales.
Stock is at all time high, and I would like to lock in some of the profits without tax liability for this year. If I sell short against the box do I defer the tax until covering the short after January 1st? At that time can I then keep the 800 shares and buy other shares to cover the short still maintaining LTCG for the 800 shares?
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