I appreciate everyone's input, and there is a bit more to that.

My first reaction is that if he were arrested, it could seriously harm him getting into a good college. When I said this to my friend (his mother), she sort of scoffed and said that he isn't currently going to school and they're looking into an online / home school program for him. He is also smoking cigs openly and my friend (his mother) has noticed several bottles missing from her bar. She has no idea how long they've been missing, because she really doesn't drink often, the bar is mostly for show and for guests.

It scares the hell out of me b/c we also have a son that age.
He knows we smoke. We don't do it indoors (lovely garden), and we don't do it in front of him, but we will ask him to step inside for a moment while we smoke. It's the most respectful and least hypocritical method we've found thus far. (any suggestions on that one are fully welcome!)

but the school thing really bothers me. And the selling. And the cigarettes. It's just a terrible recipe for an otherwise really great kid. bottom line: his mom is so concerned with being "cool" that she's allowing him to get away with FAR TOO MUCH, and like I said: he's generally a damn good kid.
Yeah, it will go away from his record when he turns 18, maybe, maybe not. There are administrative glitches that have FKD some lives up forever. Colleges will see it. His future GF's fathers will see it. Nothing really "goes away", it just becomes harder to find.

I don't want to overstep my bounds with this friend and tell her to buckle down on her son, but it seems that is the only thing to do. Plus: I don't want MY son associating with him until this is a little bit out of his system or my son catches up to his experience levels.

It's a tense, weird situation. :wtf:
All advice is very welcome.