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Mayweather talks insane gambling wins/losses Gaming. If you think that’s the lesson to gambling, you’re right. Except, three weeks later, Karas borrowed $40, and won $1 million. their winnings or throw away their win / loss report without first thinking about the tax implications. Pursuing gambling as a business is not a step to be undertaken easily or casually, though. Americans love to gamble. Humans love to gamble for that matter. Whether you bet on football, play poker or bet on the horses, your winnings are taxable and you must report them on your tax return.

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