|Appearance(s)||The Betrayal of Jimmy|
- "I used to be a real nice guy. Got a problem? You call Jimmy. In a jam? You call Jimmy."
- — Jimmy
Jimmy is a contract killer and enforcer who will accept any job for money. From trashing cars to shooting up buildings, he does it all. Jimmy is bald and clean shaven, except (sometimes) for sideburns.
The Betrayal of Jimmy
Jimmy was hired by the Don of the Gravina crime family, Sal Gravina, along with his old friend Tam Brodie, to do various tasks for them. He then gained contact from their boss Judge Hillwood. At the end of the DLC, Jimmy is told to steal a Berkley Kingfisher. Once he gets there, the police show up. The car contains drugs, so Jimmy is sentenced to 15 years in prison. Sal Gravina had set him up.
In Jimmy's Vendetta, Jimmy breaks out of jail in a prison riot that he took advantage of after being freed by his contact within prison. He manages to escape through the sewer lines, and takes residence in Oyster Bay. Jimmy then starts to take his revenge on the people who set him up by killing all of their associates, and destroying their fronts and businesses. Jimmy also does some car theft on the side to make some money. Eventually, Jimmy kills the men who set him up, Sal Gravina and Tam Brodie. However, Judge Hillwood was still standing. Jimmy eventually assaults Hillwood's fortified mansion, kills Hillwood, and sets the mansion on fire.
- He bears a striking resemblance to actors Bruce Willis and Ed Harris, including his bald hair and masculine physique despite his old age.
- Jimmy has similar traits to Hitman's Agent 47.
- His last name is never revealed.
- Jimmy has the same prison number as Vito Scaletta in Time Well Spent (19790).
- Jimmy is currently the oldest playable character in the Mafia series, appearing to be in his late 40's or early 50's.
- When he calls the police department for a bribe he says "It's Jimmy, yeah, that Jimmy," indicating that he is well known on the streets of Empire Bay.
- Harry seems to know Jimmy as he lets Jimmy in his armoury after Jimmy confirms it is him.
- His trademark outfit is a black casual suit with blue/black tie and dark blue/black shirt.
Notable Murders Committed
- Eddie Fu (Empire Bay Triads)
- Elroy Tussle (Bombers)
- Duke Tussle (Bombers)
- Daniel (Bombers)
- Charon (Bombers)
- Sal Gravina (Gravina Crime Family)
- Pepe Gambino (Gravina Crime Family)
- Ettore (Gravina Crime Family)
- Federico (Gravina Crime Family)
- Tam Brodie (O'Neill Gang)
- Sean Brodie (O'Neill Gang)
- Bill Brodie (O'Neill Gang)
- James Brodie (O'Neill Gang)
- Judge Hillwood (Independent)