Thanks for clarifying things. Although you've said that the men would be basically down and outs, would this character be workable?
Tony is the Don's nephew, a cocky and violent mobster in training. Being close family he has always been protected when his hot blood landed him in trouble. Last night he overstepped the mark. In a bar where a couple of rival mobsters were drinking, he acted tough to impress his friends and made a move on one of the rivals girlfriends. The rival protested and Tony went crazy and hit the man so hard with a pistol butt that he killed him. The dead man was another bosses son and has demanded blood in return from Tony's uncle.
The Don calls Tony to his office and tells him to avoid an all out war he has to hand Tony's dead body over. He then gives Tony the option of transferring to a female body, or simply be killed. Tony chooses to live and his old body is shot through the head after the transfer and delivered to the rival boss.
Although it was his choice, Tony hates what has happened. His uncle still sees a use for him, having the chance to push a family member undetected into his organisation to keep an eye on his lieutenants. Tony has to start at the bottom of the organisation to avoid suspicion.