Roulette Wheel Scene

The roulette wheel was rigged...he thought his buddy running the wheel would hit the button and have him win....But that was his delusion...it was too much money and the guy running the wheel would have risked his own life by cheating at that moment.

Hooker's behavior at the roulette table is wholly consistent with what we know of his type even this early in the movie. We know he's a player, we know he's impulsive, we know he thinks he's indestructible, we know he's a rebel. So, we're not at all surprised to see him bet everything he has. He's shocked when he loses because such personalities who feel on top of the world, and we know he felt that way after that day's bigger than average score, are always surprised when they lose. The fact that he's out of touch with reality becomes evident when he's cheated at the table and he should've known better.

The movie is about Hooker and his change from the type of character he is to begin with and who is has become by the end when he turns down his own cut of the sting. At the end he's in touch with reality.