Seriously? With a criminal record, he's unlikely to be able to get a full time, long-term job. So he will bounce from one short term job to the next, filling the gaps with unemployment.
Further, he's probably likely to commit more crimes, even if petty crimes like drug use, so he will cost you and me in police time, court time, jail time. And he's more likely to get busted for those petty crimes since he will be living in high-crime, high police areas; whereas a rich kid would not be busted for simple possession a poor kid with no job will be.
Then there's the predictable drain on social services, subsidized housing, and so on.
It is far, far cheaper to pay for this kid's college at an Ivy League school than it is to send him to jail.
That's the part that the "law and order" "lock 'em up and throw away the key" nutjobs fail to understand.