However, during their stay they actually won $2,000 and lost $400. In Shollenberger the petitioners entered a casino with $500 and left with $1,600 (an $1,100 taxable gain). 2009-306 (2009) that you can report as gambling winnings the difference between what you started and ended with if you keep records for each session. However, in answer to your question about how your stake factors into your winnings, the Tax Court held in Shollenberger v Commissioner T.C. The IRS only allows you to deduct gambling losses up to the extent of your winnings. The other answers involve situations where there were multiple bets with some bets resulting in a loss. Your Form W-2G will show $50 in “Reportable winnings” in Box 1. If you bet $100 to win $50, only your $50 in winnings are taxable (assuming you only made one bet).
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