If you do it the way you laid out, yes you'd pay short-term cap gain rates. Forummm makes a great point, no need to sell and donate cash. If you want to donate just the 10%, not 10% + earnings, just donate most of the shares. Alternatively if you prefer giving cash for some reason, while not optimal, you could still do it and pay long -term rates. You'd just have to hold slightly more than a year.