> There is no way to give money to charity in such a way that you end up with more money than if you had not given to charity You note that the particulars of

> There is no way to give money to charity in such a way that you end up with more money than if you had not given to charity You note that the particulars of valuations can allow people to claim a larger deduction than if they sold the asset and donated the proceeds. But that's precisely the point. If you have a $10 million tax bill, and you're looking to keep as much of that $10 million as possible, then donating an asset to charity with an optimistic valuation puts more money in your pocket compared to selling it for actual market value (especially since you would pay further taxes on the sale). The fact that you never see any of the money, because you took it as a deduction instead of a check, is irrelevant. At the end of the day, after your tax bill is settled, you have more money in the bank compared to selling, and that's all that matters.