Can I simply direct my financial advisor to sell my securities and donate the proceeds to the USS Midway Museum?
You can but it might not be a good idea. Here’s why. In order for you to avoid capital gains on the contribution of appreciated stocks or other securities, they must be transferred to the charitable donee before they are sold. Otherwise, you will realize the capital gain personally. Conversely, securities that have declined in value since you purchased should generally be sold prior to contributing them. In most cases, you would be better off selling the securities, claiming the capital loss that you can use against other capital gains, and donating the cash proceeds from the sale. Again, we suggest you consult your investment and tax advisors to determine the best securities to donate.