How does he do that? The IRS allows you to deduct up to the amount of your gambling winnings, so you wouldn't get a refund, unless the state was automatically w

How does he do that? The IRS allows you to deduct up to the amount of your gambling winnings, so you wouldn't get a refund, unless the state was automatically withholding some of his winnings. There is also the possibility that he set up a company that only engages in gambling, so it can have a Net Operating Loss year over year.