Interesting theory. So, on that theory, and assuming there was really a note that the donor originally expected to collect, or at least had that right along with the right to cancel should he so desire (i.e., it was not intended as a gift until he forgave it), and despite that the cash payment happened X years ago, so the charity would be hard pressed to sign an acknowledgment this year for cash received, and further assuming that the charity's financial condition had deteriorated such that full collectibility was doubtful and therefore the note's market value had declined, he'd be OK taking the contribution deduction as cash in the full amount of the original loan, not as property at its (reduced) value, all of which would give him a contributions deduction rather than a personal bad debt, all that said, is there some authority for the position?