Jimmy "The Grape" is a close business friend of Jackie Estacado and an old school associate of the Franchetti crime family.
He stays at the subway station most of the time in The Darkness. He was the one who informed Jackie about Paulie's money savings for the Chicago mob, and who told Jackie that Paulie and Eddie Shrote had kidnapped and taken Jenny to St. Mary's Orphanage after they brutally beat him. Later, after Paulie's assault on Aunt Sarah's house, Jimmy was the one who offered Jackie temporary donship of the Franchetti family.
He returns in the game, and gives some missions to Jackie. His mental hospital reality counterpart (Dr. James) is shown as a strict elderly man who tells Jackie (during the mental hospital realities) that his "delusions" are inspired by mafia fiction. Dr. James tells Jackie that while mafia fiction is entertaining, it is unacceptable for real life.
Jimmy wears a purple hat, jacket and pants. He has an New York accent, and usually speaks with some eloquence, as befitting his status as an old-school mobster.
- In The Darkness II, when talking to Jimmy in Jackie's office, he says "I knew this guy, Vito Somethin'-or-other. Me an' him did some time in the fifties. Boy, could that kid jack a car." This is a reference to the video game Mafia II, another title made by 2K Games, and its protagonist Vito Scaletta.