Jimmy is the titular protagonist and player character in the Mafia II DLC packs The Betrayal of Jimmy and Jimmy's Vendetta.
Jimmy is an experienced freelance criminal who will do any job for money.
The Betrayal of Jimmy
Jimmy begins working for Gravina crime family boss Sal Gravina and does various jobs for him and his friend Tam Brodie. He then gained contact from their boss Judge Hillwood. Near the end of the DLC Jimmy is sent to steal a car, however is stopped by police and sentenced to 15-years in prison as the car had contained drugs.
Jimmy breaks out of prison during a riot and returns to Empire Bay. He begins getting revenge on the people who set him up, and begins taking down the Gravina crime family and the Irish mob. Jimmy faces off with Sal at the docks and kills him, finishing the family. With only Judge Hillwood left, Jimmy heads to his mansion. Picking off Hillwood's men, Jimmy tacks down the Judge and guns him down, critically injuring him. Jimmy douses the mansion in gasoline and sets the place on fire, and finishes off Hillwood with a bullet to the head.
- Jimmy is the oldest playable character in the Mafia series.
- Jimmy resides in the same cell Vito Scaletta was in during the Mafia II chapter "Time Well Spent".
- His likeness appears to be based off Bruce Willis and Ed Harris.