He should try getting a pardon. Some cities have charities that can help cover the cost of the pardon if you look. Sorry, but with the amount of people looking for work, they have to weed out anyone with a less than perfect record.
What kind of jobs has he been looking for? Depending on his legal issues, it could haunt him for basically forever. A few of the guys from my group had that issue, where they couldn't get anything other than the construction job they had now, and only because they were working for a relative. Do you two have any family or friends that could possibly help you?
He has been looking for anything that does not recquire one to have an university diploma to do. Grocery stores, work supplies stores (Overalls, work clothing), to be a santa in a mall, for our city itself, deskjob supplies store, clothing stores, computer shops, anything realy, apart from odd hours jobs that he can't do because of his health. I could check with any of our family, one such job he is waiting to see if he can do it.