Billy didn't tell her he helped her to get on Jeopardy? I would have told her azz I got her on Jeopardy, and she probably would not have left his azz like she did. Plus, she is tooooooooooo fine.
Or, instead of gambling he should have just given Sidney the money. The $2000.
It always used to bug me that when Sidney wants to play the final game to recover the losses of the burglary, he never said to Gloria that if it wasn't for him, she would never have made onto the show in the first place...
Me personally I think that Billy wasn't doing it for the money, it was for the glory and also in the end to help out the one person who helped him get his girlfriend back.