5. Drunk Driving Expenses.
Some guy had a little too much to drink at a party, he waited for hours until he was okay to get his car. Still, he drove off the road and got arrested. His car was damaged and his insurance company refused to cover it, so he paid for the repairs and deducted them. It was a casualty loss, he argued. The IRS said no, but the Tax Court overturned and allowed the deduction.