By Jason Watson (Google+)
Yes, but be very careful. To deduct a contribution made to a qualified organization, the donation must not be earmarked or directed by the donor. However, and this is a big however, if you notify the organization that you prefer the donation to go to a certain person, and you state that you understand it might not, then the contribution may be deducted.
For example, your son goes on a charitable trip with a local church. If you donate money and you earmark it specifically for your son’s expenses, etc., that contribution is not allowed. But if you say that you prefer the donation to go to your son but you understand that the charity has full authority to use the money as they wish, the contribution can be deducted. Most organizations understand this arrangement, and they further understand that future donations will probably cease if they don’t “make the right choice.”
There are other situations where this preference arrangement can be applied.