Firstly, you should specify what it means to have “more money.” For one, her wealth is (to an approximation) all Amazon stock at a zero basis. She can’t spend A

Firstly, you should specify what it means to have “more money.” For one, her wealth is (to an approximation) all Amazon stock at a zero basis. She can’t spend Amazon stock, so in reality, she doesn’t have the amount of money that say Forbes claims she has. She has a massive tax lability before she can turn this wealth into money. So, you should be asking “how does this minimize her net monetary position after liquidating Amazon stock?” To that, I don’t think it’s true. Yes, she can “double count” the donation, but that would require her taxes be over 50% to come out ahead. Given she has mostly zero basis long term cap gains, I don’t think she’s even close to that rate.