Road to Perdition

In the winter of 1931, Michael Sullivan Sr, is an orphaned enforcer of Irish Mob boss John Rooney in Rock Island, Illinois. His wife Annie knows of his work, but his two sons Michael Jr. and Peter do not. Rooney's associate Finn McGovern speaks at his brother's wake, insinuating that Rooney is responsible for his brother's death. Rooney sends his son Connor and Sullivan to talk with McGovern; Michael follows them and watches the interaction from hiding. Rooney sends Sullivan to collect a debt from speakeasy owner Tony Calvino. Jealous and paranoid, Connor sends a letter with Sullivan for Calvino. Calvino reads the letter and reaches for his revolver, but Sullivan kills him and his bodyguard. The letter reads, "Kill Sullivan and all debts are paid". Sullivan rushes home and discovers that Connor, suspecting Michael has told others of the murders, has already murdered Annie and Peter. Sullivan and Michael flee Rock Island and head to Chicago to meet mobster Frank Nitti. Sullivan offers to work for the Chicago Outfit in exchange for permission to kill Connor. Nitti rejects his offer and advises Sullivan against seeking revenge. Rooney, listening next door with Connor, reluctantly allows Nitti to dispatch contract killer Harlen Maguire, whom Nitti orders to kill Sullivan. Sullivan plans to take Michael to his aunt's beach house in Perdition as a haven. Maguire tracks them to a roadside diner, where he and Sullivan converse casually while Michael sleeps in the car. Sensing danger, Sullivan escapes from Maguire with Michael, and Maguire kills a police officer in the process. Sullivan realises Maguire knows their destination, and begins robbing the banks that hold the Outfit's money, hoping to pressure the Outfit into withdrawing their protection from Connor. Sullivan teaches Michael to drive so that he can act as a getaway driver. When the mob withdraws its money from its banks, Sullivan interrogates Rooney's accountant, Alexander Rance. Rance stalls Sullivan until Maguire appears with a shotgun. During the shootout and escape, Maguire and Sullivan wound each other and Rance is killed in the crossfire. The ledgers reveal that Connor has been embezzling from his father using dead men's names, including McGovern's. Believing that Rooney will give up Connor once he knows the truth, Sullivan returns to Rock Island and confronts Rooney, who is already aware of Connor's treachery. Sullivan states that Connor will be dead anyway once Rooney dies; Rooney still refuses to give up his son, urging Sullivan to flee with Michael and raise him to be a better man than either of them. Sullivan later ambushes and kills Rooney's bodyguards before reluctantly killing Rooney. Nitti reveals Connor's location after Sullivan promises to end the feud with Connor's death. Sullivan goes to the hotel room where Connor is hiding and kills him. The Sullivans finally reach the beach house in Perdition. While Michael is outside, Sullivan enters the house, where Maguire shoots him in the back. Michael appears and points a gun at Maguire, and Sullivan fatally shoots Maguire while he is distracted. Sullivan is happy that his son did not shoot, and then dies in Michael's arms. Michael drives the car back to the elderly couple's farm and stays with them. In his narration, Michael states he has not held a gun since his father's death, and when asked if his father was a good man, he simply answers, "He was my father".