In a nursing home in his wheelchair, Frank Sheeran, an elderly World War II veteran, recounts his time as a hitman for a crime syndicate. In 1950s Philadelphia, Sheeran works as a delivery truck driver and starts to sell some of the contents of his shipments to local gangster Skinny Razor, a member of the Philadelphia crime family headed by Angelo Bruno. After the company Sheeran works for accuses him of theft, union lawyer Bill Bufalino gets the case thrown out after Sheeran refuses to name his customers to the judge. Bill introduces Sheeran to his cousin Russell Bufalino, head of the Northeastern Pennsylvania crime family. Sheeran begins to carry out jobs for Russell, as well as members of the South Philadelphia underworld, including "painting houses," a euphemism for murder, or contract killing. Soon, Russell introduces Sheeran to Jimmy Hoffa, head of the International Brotherhood of Teamsters, who has financial ties with the Northeastern Pennsylvania crime family and is struggling to deal with fellow rising Teamster Anthony "Tony Pro" Provenzano, as well as mounting pressure from the federal government. Hoffa becomes close with Sheeran and his family, especially his daughter Peggy, and Sheeran becomes Hoffa's chief bodyguard.
After the 1960 election of John F. Kennedy, Russell is thrilled while Hoffa is furious. Kennedy's brother, Robert Kennedy, who was named Attorney General, forms a "Get Hoffa" squad to bring down Hoffa, who is eventually arrested and convicted in 1964 for jury tampering. While Hoffa is in prison, his replacement atop the Teamsters, Frank "Fitz" Fitzsimmons, begins overspending the labor union's pension fund and making interest-free loans to the Mafia. Hoffa's relationship with Tony Pro, himself arrested for extortion, also deteriorates beyond repair. Hoffa has his sentence commuted by President Richard Nixon in 1971, although he is forbidden from partaking in any Teamsters activities until 1980.
Despite his parole terms, Hoffa undertakes a plan to reclaim his power atop the Teamsters. Hoffa's growing disrespect for other Teamster leaders and related crime family interests begins to worry Russell. During a dinner in Sheeran's honor in October 1973, Russell tells Sheeran to confront Hoffa and warn him that the heads of the crime families are displeased with his behavior. Hoffa then informs Sheeran that he "knows things" that Russell and the other dons are unaware that he knows and further claims that he is untouchable, for if anything ever happened to him, they would all end up in prison.
In 1975, while on their way to Bill's daughter's wedding, Russell tells Sheeran that the dons have become fed up with Hoffa and have sanctioned his murder. Reluctantly, Russell informs Sheeran that he has been chosen as the triggerman, knowing he might otherwise try to warn or save Hoffa. The two drive to an airport where Sheeran boards a plane to Detroit. Hoffa, who had scheduled a meeting at a local diner with Tony Pro and Anthony Giacalone, is surprised to see Sheeran arrive late with Hoffa's unsuspecting foster son Chuckie O'Brien and gangster Sally Bugs. They advise Hoffa that the meeting was moved to a house where Tony Pro and Russell are waiting for them, and he joins them in the car. Entering the house, Hoffa finds it empty and realizes that he has been set up. He turns around to leave, at which point Sheeran shoots him dead at point-blank range before leaving the gun atop his body near the entrance. After Sheeran departs, two younger gangsters have the body cremated to eliminate all traces of him.
After taking the Fifth in a grand jury investigation into Hoffa's disappearance, Sheeran, Russell, Tony Pro, and others are eventually convicted on various charges unrelated to Hoffa's murder. One by one, the now elderly gangsters begin to die in prison. Sheeran is eventually released and placed in a nursing home. He tries to reconcile with his alienated daughters, but Peggy, suspecting his involvement in Hoffa's disappearance, severs all contact with him. Sheeran begins seeing a Catholic priest assigned to the nursing home who gives Sheeran absolution for crimes committed over his lifetime. As the priest leaves, Sheeran asks him to leave the door slightly ajar, emulating one of Hoffa's habits.
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