I think he's totally screwed. What we know about his life so far shows that he's never been shown the value of working at something long term, only ever short term, since if the dumb short term thing fails mom and dad will bail him out. When he was in high school instead of trying to do well or work towards college he was a user/seller of drugs, despite coming from a very well off family. After he lost his network of clients (the school) he had to break into cars to support his habit instead. He got sent to jail, and now he gambles his entire life's savings every day for a living, losing it all almost every day. I don't think showing him consequences now, after his actions have worked out in his favor for over 20 years, is going to fix him. If he became homeless he would be like every other homeless addict - beg for money for "food", buy drugs/gambling, then root through the garbage for food and sleep under a bridge.