Having been staked before, I can say that it’s not as simple as, “Eddie’s on his own when he’s not using Bert’s money.” Because otherwise, Eddie could go off and play matches, and if he loses Bert has to cough up, but if he wins he could claim that he was really playing with his own money that time.
So really, when you’re being staked by someone, it’s very important for both parties to know which games are ‘staked’ and which ones aren’t. And even then, it can lead to problems. Let’s say you’re a poker player being staked into games by a friend. You play, and have a horrible run of luck and lose. So you feel bad about it, and tell your friend “Forget it. I’m sorry. I’ll play with my own money next time.” So you go out, and you win. How’s your friend going to feel about that? Of course, had you lost it would have come out of your pocket, but it’s still a bitter pill to swallow.
In this case, the relationship between Bert and Eddie was clearly over, but I don’t think it was ever explicitly stated. It was more like Eddie just saying, “Go screw yourself.” So then Eddie plays a big money game and wins, and Bert attempts to intimidate Eddie into paying him. The situation is vague enough that he can make the claim that Eddie is still under their agreement, and it’s up to Eddie to stand up to him and straighten it out, which he does.
Why didn’t Bert simply have his arms broken and take his money anyway? Because in this world even the bad guys have to maintain something of a reputation. In fact, when I played poker in underground clubs with some very ‘interesting’ people (gangsters, loan sharks, and other people flying under society’s radar), trust was *never an issue. One night I lent $2000 to a person I didn’t even know, just on reputation and because he was vouched for by someone I did know. My money was always safe with those people. One acquaintance I had was a loan shark and bookie (an honest and fair one, too, in my opinion). He ALWAYS paid up promptly when he lost a bet. As reliable as a banker. (In fact, he was the guy who vouched for my $2000). Why? If he stiffs someone they can’t exactly go to the cops. And he always could bring in ‘muscle’ if he needed to. But his reputation would be shot. No one would lay bets with him if they knew there was a sliver of a chance that he wouldn’t pay up.
So Bert still had to maintain his reputation. He had to play by the rules. He stretched them that night, and tried to push Eddie into making a stupid decision. Eddie didn’t fall for it, so Bert had to back off, or risk never being able to sit down in a big stakes poker game again, or be able to take advantage of someone else’s talents again by staking them.