|Jimmy the Grape (Games)|
Jackie Estacado (Friend)
|Real World information|
- "That fat fucking piece of shit Paulie thinks he can't be touched, right? *Wrong!* Wrong, wrong, wrong *wrong*. He's gonna be touched all right, oh boy is he gonna be touched!"
- – Jimmy "The Grape" to Jackie. [src]
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. Over the next two years, Jimmy helps Jackie to run the Franchetti family.
Two years later, Jackie is attacked by unknown assailants while he has dinner in a restaurant. After he returns home, Jimmy informs Jackie that somebody also torched their warehouses down at the docks and two of their guys got killed outside Gino's deli. Jimmy comes to a conclusion that someone is trying to takeover Jackie's business.
He also expresses his relieve, that Jackie is finally using the Darkness again and adds that a waiter recognized one of the guys who came into the restaurant tonight. That guy is Swifty, who Jackie remembers left just before he got attacked. Together with couple of their boys, Jimmy and Jackie travel to a pool hall, where Swifty runs an executive poker games. Before entering the pool hall, Jackie tells Jimmy and his men to stay behind, while he proceeds alone.
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.