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First off, is your buddy straight out telling people of his past? It doesn't seem like it. I've interviewed many people for both jobs and housing, if they aren't very honest with me I don't trust them. Why should I? As an employer or apartment manager, I run unnecessary risks by employing or renting to an ex-con, risks that I DON'T NEED TO RUN. By not being straight up with me, that just gives me more reason to say NO.
If he's straight out of jail with absolutely no recent work history, you're running into more problems by trying to get him into a "good job". It may suck, but send your buddy to Burger King for a couple months and then try again. Hey, it's money, it's effort, and it shows that he really is trying to be a good contributor to society.
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