In the early 2000s, in a nursing home in his wheelchair, Frank Sheeran (Robert De Niro) is an elderly World War II veteran. He reflects on his life leading up to where he is now, starting with his profession as a "house painter" - in other words, a hit-man. In the 1950's, Frank lives in Philadelphia, Pennsylvania working as a truck driver for a meat-packing company. He's married to Mary (Aleksa Palladino) and has a daughter, Peggy (Lucy Gallina). Sheeran starts to sell some of the contents of his shipments to a local Philadelphia Italian-American gangster known as "Skinny Razor", a member of the Philadelphia crime family headed by Angelo Bruno. After his company accuses him of theft, union lawyer Bill Bufalino (Ray Romano) gets him off, and helps Frank avoid legal repercussions by telling him to not give up the names of anybody that he was selling to. Bill introduces Sheeran to his cousin Russell Bufalino (Joe Pesci), the head of the Northeastern Pennsylvania crime family. Frank discusses his time in the war, and how he was skilled at taking out enemy soldiers. Sheeran begins to carry out jobs for him, as well as members of the South Philadelphia underworld, including "painting houses", a euphemism for contract killing. Frank is asked by a gangster called Whispers (Paul Herman) to take out Russell and his buddy Angelo Bruno (Harvey Keitel). Frank doesn't go through with it and instead brings this information to Russell and Angelo. One afternoon, Frank goes home to see that Peggy is looking upset. Mary tells him that she knocked something over at the supermarket, and the store owner shoved her. Frank takes Peggy back to the store where he violently confronts the store owner, beating him and throwing him through the glass door before assaulting him in the street, in full view of Peggy and others walking by. This leads Peggy to become terrified of her father. During this time, Frank leaves Mary for a woman named Irene (Stephanie Kurtzuba), and they later have 3 other daughters. Frank's 1st daughter Peggy (Anna Paquin), 2nd daughter is Dolores (Marin Ireland), 3rd one is Maryanne (Jennifer Mudge) and 4th is Connie (Kate Arrington). At the time Russell's boss is Angelo Bruno (Harvey Keitel). One time Frank accepts a mark to burn down a laundry competitor in Philly, without knowing it was owned by Bruno. Russell saves Frank that time. Soon, Russell introduces Sheeran to Jimmy Hoffa (Al Pacino), the head of the International Brotherhood of Teamsters (The most powerful man in the country after the President himself), who has financial ties with the Bufalino crime family and is struggling to deal with fellow rising Teamster President Anthony "Tony Pro" Provenzano (Stephen Graham), as well as mounting pressure from the federal government to reduce the influence of the Unions. Frank hits the ground running in Chicago, by destroying all cabs of the drivers who joined the opposing Union and helping strengthen Jimmy's position in the city. Jimmy's right-hand man is "Crazy" Joe Gallo (Sebastian Maniscalco). Russell's wife is Carrie (Kathrine Narducci). Jimmy's wife is Josephine "Jo" Hoffa (Welker White). Hoffa becomes close with Sheeran and his family, especially his daughter Peggy (Anna Paquin), and Sheeran becomes Hoffa's chief bodyguard while on the road. The Teamsters Union had 1 million members, and its pension account had $8 Bn in it, which Jimmy had complete control over. As kickback for investments from the pension funds, Jimmy regularly took shares in the companies and often in his wife's name. Jimmy had a client Momo Chancana (who was from the Italian Mob), who was friends with JFK's dad, back when he was a bootlegger in Chicago. So, this was the mob's connection with the Kennedys, and they helped him win in 1960. In exchange the US President was supposed to help the mob access the casinos and properties in Cuba, which never really worked out. Jimmy and his Teamsters are staunchly against the Kennedys. After the 1960 election of John F. Kennedy, Russell is thrilled while Hoffa is livid. In November 1963, after JFK is assassinated, Jimmy makes an insensitive comment to the press that Bobby Kennedy (Jack Huston), the former General Attorney, is now "just another lawyer." Kennedy's brother, Robert F. Kennedy (Jack Huston), who was named Attorney General, forms a "Get Hoffa" squad in an effort to bring down Hoffa as he wanted to "deal" with the growing power of the Unions & the Mob and in way betraying their trust as they helped put JFK in the white house. Meanwhile Russell asks Frank to deliver a shipment of weapons that JFK used for the Bay of Pigs invasion, made up army regulars and mobsters. The invasion fails and Robert goes after Hoffa with renewed rigor. Hoffa is eventually arrested and convicted in 1964 for jury tampering. While in prison, his replacement atop the Teamsters, Frank Fitzsimmons (Gary Basaraba), begins overspending the groups' pension funds and making interest-free loans out to the Mafia. Hoffa's relationship with Tony Pro, himself arrested for extortion, also deteriorates beyond repair when Hoffa refuses to help restore his forfeited pension. It just leads to them getting into a brawl, which is broken up by guards and other inmates. Hoffa is eventually released via a Presidential pardon from Richard Nixon in 1971. Jimmy contributed $0.5 million for Nixon's re-election and thus bought the pardon, although he is forbidden from taking part in any Teamsters activities until 1980. Despite his parole terms, Hoffa undertakes a plan to retake his power atop the organized unions. But Hoffa needs the votes from Tony Provenzano to get re-elected against Fitzsimmons, whom the Unions and the Mobs like. The meeting with Tony goes badly and Hoffa and Tony come to blows as neither would back down from their hatred of each other. Hoffa wants Sheeran to talk to Russell about killing Tony. Hoffa's growing disrespect for other Teamster leaders and related crime family interests begins to worry Russell. To get re-elected Hoffa goes about saying that Fitzsimmons gave 0 interest loans adding up-to a billion dollars to his mob friends and in the process sold his own union out. During a testimonial 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 not pleased 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 because if anything ever happened to him, they would all end up in prison. In 1975, while on their way to the wedding of Bill's daughter, Russell tells Sheeran that things have reached their breaking point with Hoffa, and his death has been sanctioned. To his chagrin, Russell tells Sheeran that he has been chosen as the person to do it, on fears that he otherwise might try to warn or save him. The two drive to an airport, where Sheeran gets on a flight to Detroit. Sheeran tells Hoffa he will be in town early in the day but arrives late that afternoon. Hoffa, who had scheduled a meeting at a local diner with Provenzano and Anthony Giacalone, is surprised to see Sheeran arriving there in a car with Hoffa's unsuspecting foster son Chuckie O'Brien (Jesse Plemons) and Sal Briguglio (Louis Cancelmi), another gangster. They advise Hoffa that the meeting was moved to a house where Provenzano and Russell are waiting for them. Sheeran reassures Hoffa that everything is fine, and he joins them in the car. Upon entering the house, Hoffa finds that no one else is there and believes that he has been set up. He turns around to leave the house, at which point Sheeran shoots him twice at point-blank range before leaving the gun and the body at the entrance. After Sheeran leaves, two younger gangsters take Hoffa's body to a crematorium to eliminate all traces of him. Peggy figures out that Sheeran had something to do with Hoffa's death. Hoffa and Peggy were close, so Peggy stopped talking to Sheeran from that point on. Invoking their Fifth Amendment rights in a grand jury investigation into Hoffa's disappearance, Sheeran, Russell, Tony, and others are eventually convicted and incarcerated on various charges unrelated to Hoffa's murder and die one by one in prison. Sheeran is eventually released and placed in a nursing home. He tries to make peace with his alienated daughters, but Peggy severs all contact with him. Sheeran begins to see a Catholic priest assigned to the nursing home. The priest gives Sheeran absolution in his room. As the priest leaves Sheeran alone in his room for the Christmas holidays, Sheeran asks him to leave the door open a little, emulating Hoffa's habit.
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