If your tax bracket is high enough, donating stock can reduce your tax burden more than you would net by selling it.
For example, say you executed stock options to buy 10,000 shares of UNICORN for $1 each, but each share is now worth $101.
At a 51% effective bracket (including state + federal short term cap gains), you can sell these shares for a net profit of $1,000,000 * 0.49 = $490,000. But if you donate the stock, you can write off $1,000,000 * 0.51 = $510,000 of taxes you would have paid otherwise, leaving you an effective profit of $500,000.
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