I've not gambled against any mafia members that I was aware of. But I was strong-armed once by a group of guys that had a strategy of simply raising the bet, and if their player lost, the biggest guy would threaten the winner and claim that you weren't really playing for $20 a game, you were only playing for $1 a game. And yes, I ended up surrounded by 4 guys and a huge bouncer and I had to just pull my winnings out of my pocket and let them pick through and take back my winnings and replace each bill over a dollar with a $1 bill. They lied and told the bouncer that we really were only playing for $1 a game and that I took or stole the exta money from them. And the meathead bouncer believed them -- or he was actually in on the scam too. LOL
I've also played a drug dealer. We started at $20 a game and he won about 1 game out of 4. Then he asked to play for $100 a game, I said sure. He lived nearby and left and came back with more money. Playing for $100 a game, I slowed down more and won the first 2 games. He commented that I am playing much better now for $100 than I was earlier (insinuating that I was hustling him). Next thing I know, he had called two of his "buddies" and they were watching me like a hawk and getting involved in our games and accusing me of pulling moves. The owner of the place warned me that he heard them talking that they were going to kick my @ss. I think I won between $400-500 and eventually the drug dealer stopped playing. I did get out with the money and in one piece.
I've also played a drug dealer. We started at $20 a game and he won about 1 game out of 4. Then he asked to play for $100 a game, I said sure. He lived nearby and left and came back with more money. Playing for $100 a game, I slowed down more and won the first 2 games. He commented that I am playing much better now for $100 than I was earlier (insinuating that I was hustling him). Next thing I know, he had called two of his "buddies" and they were watching me like a hawk and getting involved in our games and accusing me of pulling moves. The owner of the place warned me that he heard them talking that they were going to kick my @ss. I think I won between $400-500 and eventually the drug dealer stopped playing. I did get out with the money and in one piece.