I wish I had advice, but I would be concerned too. This is not the "Usual girls, smoking, and illegal stuff" - it's not usual, it's unusual. It is not normal to be dating a felon, at least not for the people I know. Hopefully your brother will realize that these people are only causing him pain; for example, his car was ruined. The best thing you and your mom could do is to stop saving him. The perfect opportunity would be NOT to fix his car. Say something like, "we love you, but you're old enough to make your own choices about who you hang out with and what you do, and you're old enough to pay for the consequences if you make poor choices." That's the #1 most effective thing you can do to encourage someone to change. Be loving and kind (in your words) but very very firm in your actions/boundaries, and do not give him any money for ANYTHING or bail him out from ANYTHING. My parents did that with my brother (he was 19) and it saved his butt. It really turned him around because he didn't want to be homeless, etc. I think if they'd pampered him he would have ended up in some serious trouble.