In 1926, Joe Coughlin, an Irish-American
World War I veteran and the prodigal son of
Boston police captain Thomas Coughlin, falls in love with Emma Gould, the mistress of notorious gangster Albert White, the boss of the
Irish Gang of Boston who Joe and his friends have been targeting in a series of robberies. Thomas objects to the relationship and advises Joe against his criminal activities, warning him that his wrongdoing will catch up with him eventually. White's rival,
Italian Mafia boss Maso Pescatore, finds out about their affair and blackmails Joe to kill White. Joe refuses, and instead he and Emma decide to flee to
California. To fund the trip, Joe commits a bank heist with his partner Dion Bartolo and another man, during which three police officers are killed in an ensuing chase. When Joe goes to meet Emma, he discovers that she betrayed him to White. Joe is brutally beaten by White's men and nearly killed before Thomas and the police arrive and arrest Joe for the policemen's murders. Thomas tells Joe that Emma drowned while being pursued by police. He also blackmails Chief Inspector Calvin Bondurant to ensure that Joe is indicted on a relatively minor charge rather than murder, and he is given only a three-year sentence. Two weeks before Joe's release, Thomas dies of a heart attack. Wanting revenge against White, Joe volunteers his services to Pescatore and is recruited as an enforcer for the latter's rum empire in
Ybor City in
Tampa, Florida, which is under attack by White. Joe brings Dion along and together they protect Pescatore's business in the area; the boss then sends orders for them to bring gambling and drugs into Tampa. Joe also develops a relationship with Graciela Corrales, the sister of a local
Cuban businessman who supplies most of the rum, and they are soon married. Joe befriends Sheriff Irving Figgis to get police protection for his bootlegging. Irving's daughter Loretta heads to Hollywood to become an actress but instead becomes a heroin-addicted prostitute. Irving's brother-in-law, R. D. Pruitt, a member of the local chapter of the
Ku Klux Klan who blames Joe for bringing more non-white immigrants into Tampa, starts bombing Joe's businesses and killing his men. Joe promises Irving to help get Loretta off drugs and back to Ybor City in exchange for betraying Pruitt. Joe kills Pruitt personally and has his men hunt down and kill all of Tampa's KKK members in a string of brutal assassinations. With
Prohibition coming to an end, Pescatore orders Joe to switch to selling narcotics, which he disagrees with, instead planning to build a mob casino near
Sarasota. He intends to persuade the state government to legalize gambling, but Loretta, who has become a devout Christian under her father's strict and punishing discipline, begins preaching that alcohol and gambling are against God's word. Her ministry is popular enough that the government decides not to legalize gambling. Joe recognizes that Pescatore will be enraged, particularly since Joe still refuses to invest in narcotics. During a private meeting in a restaurant to settle their differences, Loretta confides to Joe that she does not truly believe in God and her sins cannot be forgiven. The next day, Joe is despondent to learn that Loretta committed suicide. While visiting his brother-in-law, an amateur photographer, Joe finds a recent picture of Emma, whom he believed to be dead. He decides to pursue her, but only after informing Graciela first, much to Dion's dismay. Pescatore orders Joe to meet with him at a local hotel, where he reveals he has reconciled with White and given him the honor of killing Joe for his failures, planning to replace him with his son Digger. Anticipating Pescatore's betrayal, Joe distracts White by showing him Emma's picture, as White also believed her to be dead. Dion and his men ambush Pescatore's gang through a series of tunnels Joe had previously used to move rum into the hotel. In the ensuing gunfight, White, Pescatore and Digger are all killed, eliminating all of Joe's enemies in one stroke. He names Dion as his successor before locating Emma at the brothel she now works at. She relates how she faked her death to escape from White and enjoys her newfound freedom, and claims she never reciprocated Joe's love for her. Satisfied, Joe returns to Graciela. Joe and Graciela move to
Miami, where they have a son, Tommy, and devote their time to building houses for the impoverished. Driven insane by Loretta's death, Figgis tracks them down and shoots up their house, killing Graciela before being fatally shot by Joe. Joe arranges for Graciela to be buried in her homeland in Cuba and spends the rest of his days dedicated to charity and to raising Tommy, who soon voices his desire to become a police officer. ==Cast==