In New York City's Little Italy, waiter Paulie (Eric Roberts) loses his job at Sal's Bar and Restaurant after being caught embezzling, and Paulie's older, more responsible cousin, maître-d Charlie Moran (Mickey Rourke), is also fired because he vouched for Paulie. Although Charlie is angry with the reckless Paulie, he maintains a sense of duty to his Italian family and tolerates the young hustler.Meanwhile, unemployment leaves Charlie further away from his dream of owning a restaurant, not to mention he owes alimony to his ex-wife, has a pile of debts and needs money to support his pregnant girlfriend Diane (Daryl Hannah). Paulie also needs a "get-rich-quick" scheme to pay back loan sharks who financed his stake in a racehorse. After learning that a large amount of cash is being stored over the weekend at the offices of a trucking company, Paulie plans to steal the money with an accomplice named Barney (Kenneth McMillan), a middle-aged ex-con and small-time safe cracker. Charlie agrees to join the two, and shows Diane a restaurant he wants to buy outside the city, in anticipation of the "surefire" heist.On the night of the robbery, crooked detective, Walter "Bunky" Ritter (Jack Kehoe), prepares to pick up police bribery money from the trucking office safe and deliver it to officers participating in the mafia payoff. As a precaution, Bunky wears a hidden recording device in case he ever needs shielding against bribery accusations. The detective interrupts the burglary, but as he draws his gun to confront the thieves, he accidentally falls into an elevator shaft and dies. While Barney continues to break into the safe, Charlie confiscates Bunky's wallet and the recording device. After the trio escapes with $150,000, Paulie reluctantly confesses to his accomplices that the trucking company is owned by feared mafia boss, "Bed Bug" Eddie Grant (Burt Young). Once again, Charlie is furious with his dimwitted cousin, but remains loyal when his girlfriend Diane yells at him for his continuing association with his "idiot" cousin.Later, Diane leaves Charlie a note announcing she has left him and taken $45,000 of the robbery money to raise their child. While Bed Bug Eddie searches for the identity of the thieves, two police officers on the mafia payroll are anxious to locate Bunky's incriminating audiotapes after finding evidence that the detective was wired. When Bed Bug Eddie discovers Paulie's involvement, he sends thugs to confront the thief at the racetrack.Fearing for his life, Paulie provides the name of his accomplice, Barney. However, the foolhardy hustler does not escape punishment entirely as Bed Bug Eddie's thugs cut off his thumb. The mafia notifies police about Barney, but the safe cracker eludes capture. Anticipating that Paulie might be caught and betray him, Barney made arrangements to protect his wife Nora and provide for his mentally handicapped son before leaving town.After Paulie receives treatment for his hand injury, he is forced to work as a coffee boy at Bed Bug Eddie's club and one day is pressured to reveal that Charlie also participated in the robbery. Paulie joins his cousin at the racetrack, where Charlie wins $20,000 betting across the board on Paulie's racehorse. While Charlie appears more optimistic, a nervous Paulie is anxious for them to take a midnight plane to Miami, Florida. He finally tells Charlie that Bed Bug Eddie knows about his involvement in the robbery. After yelling at his cousin for betraying him, Charlie confronts Bed Bug Eddie and calls himself "the Pope of Greenwich Village" because he possesses Bunky's audiotapes. Before Bed Bug Eddie can retaliate, Paulie poisons the mob boss's coffee with lye. In the final scene, the two cousins, Paulie and Charlie, quickly walk away from the club, arguing about their future prospects.