Well I assumed that the HC of the Hamilton Rough Tricks or whatever the team is called would at least prepare him a little bit. There's rust, and there's looking like you've literally never played the game before.
If he ever truly quits the drugs and the partying ways, then he can have a good life. What a shame that as he was going down in flames he had all of those hanging out with him who could offer nothing in return. At some point, he has to go broke, right? When that happens, he will be in a high pressure terrible spot, as all bad habits come to the fore in times of real stress. He doesn't have unlimited money, so it will get ugly in a few years unless he gets straightened out.
I would like to seem him do it....one way or the other.