Q: I bought $1,000 in raffle tickets to help out my church, which was giving away a car. I don’t drive, so I didn’t care about winning. Does my $1,000 qualify as a charitable deduction?

A: No — you get no deduction. Even though your intent was to donate $1,000 to your church because you don’t drive and didn’t care about winning the car, you still purchased a “chance to win” something that has a greater value than the amount you “donated.” Charitable deductions may be taken only when the dollar amount donated exceeds the cash value of the prize.

Had you bought the raffle tickets and then given them back to the church, the $1,000 would likely qualify as a charitable donation and thus be deductible.