"One of the most tax-efficient ways to support a favorite charity or church is by donating appreciated stock instead of cash. When stock that has been held for more than one year is gifted directly to a qualified charity, the charity receives the full market value of the shares and can sell them without paying tax, because it's a tax-exempt organization.
The donor generally receives the same charitable income tax deduction they would have received had they donated cash, while also avoiding the realization of any capital gain. For example, if someone is considering donating either $50,000 of cash or $50,000 of appreciated stock, the charity receives the same economic benefit in either case: $50,000 that can be used to further its mission. Likewise, the donor generally receives the same $50,000 itemized charitable deduction.
The difference is that if the stock was originally purchased for $20,000, donating the shares allows the donor to avoid recognizing the $30,000 capital gain. If the donor still wants to own the investment, they can use the cash that otherwise would have been donated to repurchase the shares, effectively increasing their cost basis from $20,000 to $50,000 and reducing future taxable gains."
-Brent Wilsey, Wilsey Asset Management