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Message: [QUOTE="ZekeRam, post: 2579753, member: 131737"] Yea, not sure about back in the day, but you probably just didn't report it. At any rate, if you win $200, and lose $100, then you can deduct $100 from your taxable income. However, you have to report that you won the $200, so say you're in the 28% tax bracket, you'll owe $28 in taxes after it's all said and done. Let's say, you win $300, but lose $500. Well, you can only deduct $300 from your taxable income, so although you're not going to pay taxes on the $300 winnings, you're still in the hole by $200. Pretty much win/win for the IRS. [/QUOTE]