[disneysteve]

I think you need to live your life and let him live his. Absolutely under no circumstances should you ever lend him money. If I were in your shoes, I would probably talk to your mom and try to convince her not to give him money either. Explain how it is really enabling his problems and irresponsibility, not helping him in any way. It just makes the problem worse. Giving him money, bailing him out every time he gets himself in trouble doesn't teach him how to get himself out of trouble. I've got zero patience for people like that.