Need advice on collecting a very large debt....

[fnord_too]

Do you have an IOU? File suit. Also, you could tell him you are reporting him to the police. If I read this correctly, he ran a home game, then didn't pay out. If he is at all intelligent can afford to pay what he owes, he will understand that at the very least he will have to deal with a leagle sitution and that the potential down side is pretty large. (Really, it's kind of hard to live down getting a summons at work and getting hauled into court for running a poker game and stiffing a college kid. I mean here, you bought in for $2300, WON A LOT, and cashed out $1500. Even discounting the winnings, he flat out stole $800 in cash).

Getting violent would likely be effective, but that is not a good course of action. Bludgeon him with the law, he has to understand that he has a lot more to lose by not paying up than by just forking over the dough. If he claims he was cheated I would observe the following:
The game was at his house.
You bought in for $2300 and cashed out $1500
He's the one running a crooked shop.

Actually, the fact that he is not paying off may be enough to consider this running a game for profit. Really, he is not in a good position.