Episode of a show, main character gets jumped after winning at poker. (Solved)

Can anybody remind me what show this scene occurred in:

Main character and his buddy hear about a poker night that takes place with a lot of hard guys operating out of a bar. MC needs some money quickly for some reason so go and ask to join the game, they're offered a drink, MC has a lemonade or equivalent soft drink. After the first hand it becomes apparent that these guys play for far higher stakes than MC is comfortable with, but he wins the fist hand, with a tidy profit. Against objections he leaves immediately, offering some back "for the lemonade" (a $20 or something, way higher than the actual value of the drink.) As they're leaving they're jumped and lose all his money.

Later in the episode, (or a few episodes later, maybe, but I think the same one.) he's staking out a place near the same bar and he realises he can rip off the bar pretty easily but that would mean he'd have to stop doing what he's doing now. I can't remember which decision he made, I know it didn't end up with him successfully ripping off the bar so he either didn't try it or it failed somehow, but not in a way that got him seriously hurt.