but he's not learning

Consider that there are conditions and substances that impede retention.
He has (apparently) previously determined that this behavior is "optimal" for him. Nothing changes until his risk calculation says "this isn't worth it" or something better comes along... or his decision-making is over with.

The fucker is thinking only with the animal part of his brain - the amygdula

This is basically the answer. Consider addicts. Thrill seekers. Sadists/Masochists. There's a cocktail of neurotransmitters that come into play when they do some "stunt." It's enjoyable. They want that feeling to continue or grow. It escalates or accelerates.