They just locked him up in the city jail and kept him busy washing cop cars and I think they found him useful in keeping the younger inmates in line. He was Okay when he wasn''t drinking- I think his biggest sin was he didn't have too many other hobbies.
Perhaps one of the biggest problems. You have to think who raised him and gave him things like a work ethic, will power and set the standard for what influences, him.
Usually the first person you think of is the parents, but mostly I would say it's his peers. He works well under supervision obviously but left to his own devices, from what you said, he getting into trouble while drinking.
It sounds perhaps despotic but some people need to be controlled to become productive. That he wanted to be in jail is a good example that some people need this sort of invasion in their life.