Gifts of Appreciated Securities
Don't sell stock first and then give Yale the proceeds. Even though you will receive a deduction, you will pay capital gains tax on the sale, eliminating a key tax benefit of your gift.
Don't contribute securities that have declined in value. The fair-market value deduction rule works against you: if you bought the stock for $50,000 and it's now worth $30,000, your charitable deduction will be limited to $30,000. You won't be able to claim a capital loss by making the transfer to us, either.
Sell the depreciated stock, claim the resulting tax loss as a deduction, then make a deductible cash gift to Yale with the proceeds.