Don't sell the stock first!

Even though you give us the proceeds as a gift, the IRS will impose capital gains tax on your sale, wiping out the benefits of this arrangement.


Don't contribute stock that has declined in value?

First, the fair-market deduction rule works against you: if you bought stock for $50,000 and it's now worth $30,000, your charitable deduction will be limited to $30,000. Second, you won't earn a capital loss by making the transfer to us, either. It is better to sell depreciated stock, claim the resulting tax loss as one deduction, then make a deductible cash gift to Taft with the proceeds.