How can a poker player do it right? I want to be honest and pay my taxes, but I don't want to pay when I've lost money for the year. My winnings are reported in one place and my losses can only be reported on Schedule A. I don't itemize so I can't report my losses. So are you telling me that I'm "cheating" when I don't report my winnings? To report what's reportable in my case, I will show a modest profit for the year. To not be allowed to offset those winnings with my legitimate losings, wouldn't I be sort of "reverse cheating" in favor of government? I have a big problem because today is Dec. 31 and I planned to play in a big tourney right now, today. But the place where I wanted to play gives 1099 G's for anyone who wins more than $600 (not $10,000). If I play and go on to win more than $600, I am paying a "rake" of over 33%. Is there a way to do all of this reporting honestly?