In 1938, mobster Thomas "Tommy" Angelo meets police detective John Norman and seeks his help to secure his family's protection from his former associates, the Salieri
crime family. To prove that his story is true, Tommy offers to tell Norman what led to his current predicament. In 1930, Tommy is a taxi driver struggling through the
Great Depression. One night, he is strong-armed by two Salieri gangsters—Paulie Lombardo and Sam Trapani—into helping them escape an ambush by the rival Morello family. Tommy is compensated for his help and offered a position in
Don Ennio Salieri's organization, which he initially declines. However, after two Morello gangsters track him down and destroy his cab in an act of revenge, Tommy seeks Salieri's protection and exacts retribution upon his attackers with Paulie's help. Tommy subsequently joins the Salieri family, assisting with running their
rackets across Lost Heaven, overseen by Salieri's
consigliere Frank Colletti, and befriending Paulie and Sam as they carry out various jobs together. In 1932, Tommy, now a
made man in the Salieri family, enters a relationship with Sarah Marino, the daughter of Salieri's bartender Luigi, after protecting her from a gang of street hoodlums that were sexually harassing her. On Salieri's orders, Tommy and Paulie retaliate against the gang, with Paulie killing their leader, Billy. They later learn that Billy was the son of corrupt city councillor Roberto Ghillotti, who vows revenge. Worse, Billy’s friend Johnny survived the attack. In order to prevent Paulie and Tommy from being incarcerated, Sam is tasked with killing Johnny at Billy’s funeral. Tommy is ordered to destroy a brothel and kill the manager for switching its loyalties to Morello as a distraction for the authorities. Salieri also has Tommy kill a prostitute named Michelle, who was giving information to Morello’s associates. Tommy ends up sparing Michelle at Sam's request, and later assists him in killing Johnny. In 1933, Don Marcu Morello ramps up his efforts to dismantle Salieri's organization, gaining support from the corrupt police force and Ghillotti by having Border Patrol ambush Salieri’s bootlegging operation. Salieri later finds that Frank has disappeared with the family's account books, and reluctantly orders Tommy to kill him. Discovering Frank has become disillusioned with the criminal lifestyle and made a deal with the
FBI after Morello threatened his family, Tommy allows him to flee the country with his family in exchange for the books, and covers up his actions. Later, Tommy, Paulie, Sam, and another foot soldier, Carlo, help Salieri secure a deal with southern whiskey magnate William Gates, only to be attacked by more of Morello’s men. Gates survives the attack, and Salieri gets possession of the whiskey, saving their fortunes. By 1935, Salieri and Morello begin moving out into new rackets following the end of
prohibition, while Tommy starts a family and is promoted to
caporegime for his successes. Learning that Salieri is making moves to gain control over law enforcement, Morello attempts to have him publicly killed. After Tommy saves him, Salieri realizes Carlo was the one who betrayed them to Morello. Salieri kills Carlo and declares open war on his rival. To weaken Morello’s political connections, Tommy assassinates Ghillotti during the latter’s birthday celebration. Salieri also targets Morello’s young brother Sergio, who has managed to escape every attempted hit on him. Tommy manages to finish off Sergio, allowing Salieri to take control of the dock union. The war eventually comes to an end after Tommy, Paulie, and Sam kill Morello himself as he attempts to flee Lost Heaven on a private plane. By 1938, the Salieri family is in full control of Lost Heaven's rackets and ruthlessly eliminating anyone who opposes them. Salieri tasks Tommy to assassinate Congressman Hank Turnbull, who intends to remove anyone associated with organized crime. Tommy is successful, but later feels remorseful after finding out from Sarah that Turnbull voted favorably for the
Nineteenth Amendment. When Tommy, Paulie, and Sam agree to recover a stash of diamonds hidden amongst a shipment of impounded cigars, they are shocked to discover heroin instead. Enraged by Salieri's deception and involvement in the drug trade, which he explicitly forbade them to ever engage in, Tommy and Paulie decide to carry out a bank heist that will allow them to retire, without cutting Salieri in. Although the job is a success, Tommy gets concerned for his family’s safety and tells Sarah to take their child and find a place to hide. Tommy later finds Paulie dead in his apartment the following day, and the stolen money is missing. When he meets with Sam to discuss the matter, he learns that Salieri ordered him to kill Tommy and Paulie for going behind his back, and that Frank and Michelle were murdered by Salieri's men after Tommy's past cover-ups were exposed. Tommy survives Sam's ambush and mortally wounds him. Though Sam tries to appeal to Tommy's humanity and offers to help him fake his death in exchange for sparing him, Tommy finishes Sam off to avenge Paulie. Back in the present, as Tommy finishes relaying his story to Norman, he offers to testify against the Salieri family in exchange for a reduced prison sentence and protection for his family. Norman agrees, being a father himself, and the resulting investigation and mob trials lead to the Salieri family, including the Don, being convicted and sentenced. After serving eight years in prison, Tommy is reunited with his family as they are all placed under witness protection and relocated to
Empire Bay. Tommy lives a peaceful life with his family until 1951, when two hitmen approach him. Accepting his fate, Tommy is shot and left to die on his front lawn. He succumbs to his wounds, surrounded by his family, happy that they are now safe. The game ends with a speech Tommy gave at his daughter's wedding about the importance of family, concluding that while everything else comes and goes, family is forever. == Development ==