Only to the extent that the purchase price from the charity was in excess of fair market value of the piece.
With collectible items like vintage watches or cars, that means hiring an expert to express an opinion on the value of the item as of the date of purchase. In addition, the charity would need to provide you with a letter acknowledging your expert’s opinion and agreeing to the amount of the contribution in excess of value.
With large ticket, highly publicized auctions like Mecum or Barrett-Jackson, or even the charity watch auctions that Antiquorum used to run, the appraisal arrangements are usually in place long before the auction begins
With smaller items like watches from Goodwill, you’ll need your own paperwork trail to give the IRS if they question a charitable deduction on your personal income tax return.
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