[jb9]

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But does it make sense to take a shot at a medium to big buy-in tournament to offset poker winnings for tax purposes?

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No it doesn't. Thinking of poker losses as some kind of "tax shelter" is really nonsensical.

If you do lose money playing tournaments, then of course that is a loss that offsets other wins for tax purposes, but you will receive no benefit since it's better to pay taxes on $10,000 than to lose $10,000 unless you are in the 100% tax bracket in which case it is a wash.

If you are worried about your tax liability, pay a qualified accountant, lawyer, and/or financial advisor to explain your options (this advice will often be much better than message board advice).

Donate to a charity or something.

If you have some money burning a hole in your pocket and want to take a shot at some high buy in tournaments, go for it. But play to win, not to throw away your profits so that someone else can pay taxes on them (the government really doesn't care if you pay the taxes on that $$ or someone else does).