Seems pretty sleazy, you can't take a tax deduction for money you didn't actually give them.
But say you buy in for $100 and lose it. Then buy in for another $100 and double it. Leaving the place with your original $200 and reciepts for $200. An honest fellow could take offsetting charity deductions and gambling winnings on the federal, but NH now taxes winnings regardless of losses. So be careful.
I was at a craps table in Foxwoods a few years back, a guy bought in with 18 $100 bills and bet $300 on each number. Let it sit for one roll and then brought it down and put 18 black chips in his pocket. Then he did it again with another 18 $100 bills. On the third try the shooter sevened up and he lost $1800. He did this a few more times, then walked over to the window with a huge pile of black chips and got cash and a receipt. His cash of unknown source, was now perfectly legal gambling winnings.
lots of funny things happen at casinos.
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