I'll do one even better. Let's say you give $50 to your charity from your $100. Then you "borrow" it back from the same charity to invest. You chose a high div

I'll do one even better. Let's say you give $50 to your charity from your $100. Then you "borrow" it back from the same charity to invest. You chose a high dividend investment strategy and make $10 in dividends alone. You pay $17.50 on your taxable income ($50) and $1.5 on taxable gains ($10). You can donate, borrow, and spend through that charity until the day you die. And you would still pay less in (19%) than your average working stiff.