Tommy Angelo meets detective Norman at a restaurant and offers to tell him everything he knows about his boss, Don Salieri, and his criminal activities, in exchange for a shortened sentence and protection for him and his family. He recounts his time back in 1930 as a taxi driver and a chance encounter with two of Salieri's henchmen, Paulie and Sam, who he rescues from hitmen working for Salieri's arch-enemy, Don Morello. The next day, he is attacked by the same two hitmen, but manages to run to Salieri's bar, where the two attackers are killed. Indebted, Tommy agrees to work for Salieri and the organization and starts a relationship with bartender Luigi's daughter, Sarah, whom he protects from a group of men that try to attack her. In revenge, Tommy and Paulie attack two of the men, killing one, who is later revealed to be the son of a city councilor, who is a friend of the mayor and Morello. Salieri's consigliere, Frank, orders Tommy to blow up a brothel who's owner has begun working for Morello and assassinate a target who has been providing information on Salieri. When Tommy confronts the informant and realizes it is Sarah's friend, Michelle, he is unable to kill her and instead orders her to leave the city and never return. Tommy later marries Sarah, and she gives birth to his daughter.
In 1933, during an assignment to buy a large amount of Canadian whiskey at a farm, Tommy and Paulie are ambushed by a group of corrupt police, resulting in the loss of the shipment and the near death of Sam. The same day, Frank hands over the account books to the police, providing enough incriminating evidence to put Salieri in prison; Salieri orders Tommy to find out where the books are and eliminate Frank. After Frank reveals that he betrayed Salieri because the police took his wife and daughter hostage, and tells him the location of the books, Tommy allows Frank and his family to flee to Europe, while Tommy fools Salieri into believing Frank is dead. In 1935, Tommy saves his boss from being assassinated at a restaurant, that was set up by Salieri's bodyguard-turned-traitor, Carlo, who is later killed. Declaring war with Morello, Salieri has Tommy and Paulie assassinate the city councilor and Morello's brother, Sergio, which stops much of Morello's income. These actions shatter the Morello crime family, allowing Tommy, Paulie, and Sam to finally kill Morello under Salieri's orders.
During a mission to steal a batch of Cuban cigars for Salieri, Paulie suggests a plot to rob a low-security bank, but both Tommy and Sam refuse, out of fear and loyalty to the family. After they complete the job, Tommy and Paulie discover that the boxes contain a considerable amount of hidden diamonds, some of which Paulie is tempted to steal, but Tommy convinces him otherwise. Deciding that Salieri was well-aware of the diamonds and intended to cheat him out of his fair share, Tommy joins Paulie in his bank robbery plan, which they successfully pull off. The following day, Tommy arrives at Paulie's apartment to find him murdered and the money gone. Sam rings the apartment, and tells Tommy that Salieri knows of the bank job and that they should meet at the city art gallery. It is revealed to be an ambush set up by Sam, who informs him that Salieri ordered their deaths because of the unauthorised bank job, and because he spared Michelle and Frank's lives, both of whom were eventually found and murdered by the mob. After a lengthy gun battle, Tommy is finally able to kill Sam, who delivers one final warning about Salieri's power.
Tommy then tells Norman that he and his family fled to Europe before he decided to return in order to testify against Salieri and ensure the safety of Sarah and his daughter. Norman agrees to put Tommy and his family under the protection of the police, leading to the arrest of Salieri, who is sentenced to life in prison, and 80 other gangsters, some of whom are executed. After the trial, Tommy is relocated to the other side of the country where he starts a whole new life and changes his name. In 1951, an aged Tommy waters the grass outside his house, when two men pull up in a car behind him. They address Tommy by his real name (which was changed beforehand by the FBI) and tell him that 'Mr. Salieri sends his regards', before shooting him with a double-barreled shotgun.
As the two men flee in their car, a mortally wounded Tommy lies on the grass, lamenting what has happened to him, Paulie, and Sam simply because they wanted better lives but in the end got nothing at all.
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