On the basis he's more of an independent person (who could turn antagonistic) I'm really hesitant to give him the "ok." And he's not one for authority, the Gvn is pretty strict with guidelines and wouldn't want to invest in such a risk. While the background of the character does explain his social issues, I'm never really a supporter of characters who have so much bad luck in their life (ex: divorce, alcholism, criminal record) because it's such a risk to have characters who have gone through so much crap. They tend to wear it like armor and your character hasn't really gotten past it all. It's just a lot of red flags as a GM. If you want your character to be more of a real antagonist, we'd nee to talk further since I tend to give slots to people who've showed their activity and merit in the story itself down the line.