that's why he's crying - it's an overwhelming mix of emotions.

on one hand, he obviously doesn't want to whip his best friend's ass, but on the other hand, all this shit monty's saying to provoke him is somewhat true. he's wanted to fuck naturelle since he first saw her and he's jealous that monty's been afforded such a nice lifestyle without having to work for it like he has.

mix that in with the fact that, while he's sad monty's going to jail, he kinda, in the back of his mind, thinks he deserves it.