I read the first few pages and then it got to 10 and I stopped, so I apologize if I make some points that have already been stated.
The situation with Upshaw certainly seems pretty serious, but with the amount of picks the Celtics have these are the types of picks they need to make. I wouldn't use a pick before 33 on him, and even then, maybe we could stretch it to 45. It may work and it may not.
Secondly, I don't have proof of this, but I really think the professional sports are cleaner than college sports. Maybe he needs to be on a professional sports team with constant support, a close knit team, and trainers all over the place. Sure college is like that, but there are also thousands more kids on campus getting into all sorts of crap. I just graduated from a small Jesuit college in NY a couple weeks ago. I could get any drug I wanted within an hour (I am not a user at all. Just trying to make a point). Not to mention, Upshaw is probably one of the most popular guys on campus, and people are just begging to party with him. I think his transition into professional sports could actually help him, and what better way to do it when a great coach and front office like the Boston Celtics.