I've got an ex-con token guard, who's got a smart mouth, and a flashing rapier.
He's a swashbuckler who is dependent on his quick wit.
He was a petty thief, who got caught because of his lack of planning, rather than lack of skills. He's decided that working for the Man is safer than working with other, truly bad people. He really thinks he is destined to be the leader, the planner, the man-in-charge.