In 1930, Tommy Angelo (Michael Sorvino), a local taxi driver, is strong-armed into helping two mobsters working for crime boss, Don Salieri (George DiCenzo), escape from an ambush planned by members of the Morello family, and is compensated for his trouble with a promise of assistance if he requires it. The next day, two thugs attempt to kill Tommy, who manages to lure them to a bar owned by the Salieri family where they are promptly gunned down. As repayment, Tommy is recruited as an associate and assigned to work alongside made men Sam (Matt Servitto) and Paulie (William DeMeo). Two years after joining the Salieri family, the restaurant’s bartender, Luigi, informs Tommy that strange men have been harassing his daughter Sarah (Cara Buono), who passes on the information to Salieri. Outraged at the news, not because of the men’s inappropriate behavior, but because of their description matching those of the men that had been causing trouble in his territory, Tommy and Paulie are tasked with scaring the punks off, though while completing the job, the pair end up killing one of the leaders of the gang who turns out to be the son of a prominent city councilor. Following the job, Salieri’s consigliere, Frank (Dan Grimaldi), sends Tommy to plant a bomb in one of Morello’s brothels and then later tasks him with eliminating an informant within their ranks. Upon learning that the informant is Sarah’s close friend Michelle, Tommy spares her life and sends her out of the city. He subsequently marries Sarah, who a few months later gives birth to a daughter.
In 1933, the following year, while collecting a shipment of whiskey for bootlegging, Tommy, Paulie, and Sam are attacked by policemen on Morello’s payroll, barely escaping with their lives. The following day, Salieri orders a hit on his consigliere, after Frank provides evidence of his money laundering activities to the authorities, assigning Tommy to the job. Chased to the airport, Frank eventually explains his motive for betraying Salieri was due to his desire to protect his family. Revealing to Tommy where the evidence he took was hidden, Frank is allowed to live, faking his own death before fleeing to Europe. Two years later, Salieri survives an assassination attempt by his traitorous bodyguard Carlo, and in retaliation, travels to his apartment with Tommy to kill him, before eventually focusing his attention on weakening the Morello family, ordering hits on Morello’s underboss and brother Sergio, as well as a city councilor in his pocket, which Tommy successfully carries out. With his rival’s power greatly weakened, Salieri orders a hit on Morello (John Doman), with Tommy, Paulie and Sam chasing his armored limo off the edge of a bridge under construction. With Morello dead, Salieri seizes control of his territories throughout Lost Heaven.
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