One idea I though of in the past: if you have a very high income, your income tax rate can approach 50% (state+federal). If you donate appreciated assets to a D

One idea I though of in the past: if you have a very high income, your income tax rate can approach 50% (state+federal). If you donate appreciated assets to a DAF, and break the effects down by basis+gains, the numbers look like - 50ish% back after deducting the given unappreciated basis, - Selling the short-term gains would cost you half the profit, so the charitable deduction gets you roughly 100% of the after-tax profit from the trade back in your pocket. (Plus the upside of sending money to charity.) The math doesn't work out for long-term gains though, and obviously works best when the asset has appreciated strongly. Not sure about the legal treatment of partially-donated options spreads or other complex hedging tricks to manufacture these gains and offset them against a loss. Not tax advice etc, all just guesswork.