OK, so they're in a motel. He tells Ryan Reynolds that he lost all his money and he needs him to stick it out with him. They go to the horse track; and Ryan Reynolds secretly bets on a DIFFERENT horse than Gary?
Why? Was he trying to get rid of him? Did he know he'd lose? I got completely lost there, and then more lost when he was engaging is sadistic behavior like getting his ass kicked...what was Ryan Reynolds deal?
Ryan Reynolds was trying to get him to bet on horse #1, because he knew it would win. It had the lowest odds and he figured he could win. We don't know how much money Curtis has, but its not enough to cover a trip to Macchu Picchu. (or support Simone while they go on vacation)
Gerry then bets on the long odds horse because its bigger payout but less likely to win 1 :40. But that horse loses it. Gerry is so focused on winning that he didn't even know that Curtis left out 200 of whatever amount he gave them for one last shot. But secretly Curtis bets on the number one horse. Curtis tried to warn him but Gerry is too focused on one big payout.
Seeing that Gerry won't stop, Curtis decides to not tell him about his own bet of the number on horse, and gives him 100 bucks for the trip home and pretends he is out of money too.
I can't figure out the basketball scene. I think that Curtis talks a big game but most of his stories are *beep* like when he waxes off on Tony Roundtree. Same for when he visits Simone and makes promises, but then bails for six months before seeing her again. He also says he loves her and will like be with her but can't provide, like when he asks the concierge at the hotel at the end if she wants to go. He plays life fast and loose, just like how he gambles.