First, I don't want this young person to go to jail - quite the opposite, in fact.
Second, when I was a teenager, my Dad was a police officer and my Mom worked in a Catholic church. I rebelled hard and got in trouble for wonderful things like wearing a Bad Religion shirt to my Catholic school, or writing obscenely long, self important indictments of Christianity in Christian Ethics exams, or driving at extremely high speeds around the school parking lot, listening to the Ramones and playing "Scare hockey players."
My very first, formative experience with computers was actually playing Shadowrun on a BBS. Had I gone to high school post-Columbine, that game would have gotten us all kicked out of school and likely thrown in jail. Thankfully, nobody ever found out what we did or the kinds of things we said online.
I was an especially pretentious teenager and fell under the guise of 'straight edge punk', so I absolutely shunned drugs and alcohol and stopped being friends with people who drank or got high. In retrospect, that pretentiousness likely kept me out of serious trouble and I'm quite glad for it.
Long story short, I rebelled hard and was friends with many kids who rebelled equally as hard, or even harder. Unfortunately, in the 18 years since I graduated from high school, a shocking number of the people who got me through high school have died because of drugs and suicide.
So yes, I rebelled. And yes, I did many things solely for shock value. However, I also lost some really good people because we didn't get the help that some of us (myself included) needed. Consequently, I take the view that some things are far enough away from the norms to justify further intervention.