Re: Need advice on collecting a very large debt....
Options:
1) Force- Do you know anyone who would be well suited for this sort of thing? If you send the right the type of guy, a simple "Pay up or else" would probably be all it would take assuming the guy has the money to pay. Do you know any bookies? They could probably put you in contact with someone that would be more than happy to collect the debt for a percentage.
2) Blackmail- You say this guy is respected in the business community. Does he have a family, and if so do they know about his gambling problem? Also, if the police were aware that he was running a poker game AND cheating his players, I don't think that would be very good for his reputation. Also, if he's degenerate enough, the mere threat of spreading the word to other local poker players so that he can no longer get a game may be enough.
3) Theft- If you are anyone you know are willing/able to go this route, you could just take something of his that is of greater or equal value to the debt. Also, since you yourself have already been cheated here, on a moral level, I think you would be perfectly justified in cheating him in an even larger heads-up match (CASH buy-in of course, and make sure it is set up such that you will have no problem actually leaving with the money, i.e. have some large friends present)
4) General Threats- Whether you could do this credibly or not depends a lot on your "table image" with this guy, but you could simply inform him that if he doesn't pay up, you will do everything in your power to make his life a living hell.
The principle in this matter is much more important than actual 8k IMO. You MUST somehow collect this debt even if you must do reprehensible things. You need to send a message to him and everyone else that is aware of this matter that you are not someone to be fcuked with.
Quite frankly, the fact that this guy would even consider telling you to go [censored] yourself reflects poorly on you. I'm not saying you should be going around acting like Joe Pesci or whatever, but to some extent you do need to present yourself in such a way that people know that if they [censored] with you, bad things are likely to happen.
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