I think it's a failure of our legal system that he has not been institutionalized.
By his third offence it should have been blatantly obvious to the judge that this dude needs help, and that he's not mentally competent to decide whether he needs that help for himself .
Now I'm not saying he belongs in Arkham asylum, But he at least needs to be put in a group home permanently. The solution isn't to give him a job because it masks the fact that this guy lacks critical thinking skills and has no grasp of cause and effect. I'm willing to wager that his financial, social, medical, and educational life regarding matters outside of the transit system is a train wreck(yes pun intended).