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The film starts with a boy standing on the shore. This is Michael Sullivan Jr, who says many people call his father a monster, some call him a saint, but the 2 of them spent 6 weeks on the road together back in the 30's.

The film takes place in and around gangland Chicago. Michael Sullivan Sr. (Tom Hanks) is involved with the Rooney crime family. He's something of a hitman a lieutenant, an excellent marksman, very imposing. We see him taking his 2 sons, Michael and Peter, along with his wife, to a wake at Mr Rooney's (Paul Newman) house.

The house is huge, and once inside, Peter does not want to see the body, so the 2 Michaels sit and pray together. Soon Old Mr Rooney appears and says he wants to have a word with the 2 boys. They go off and play dice, and Michael comes out ahead. Rooney tells him to go up to the study and get it from his jacket. When Michael gets to the study, the young Connor Rooney is smoking in the study and tells him to come back later.

Later on, Rooney makes a speach about the deceased, a business partner of his. His brother Finn, shaken and possibly drunk, comes forward to read a small speech. It quickly turns negative about Rooney, and he is lead off stage by Sullivan and the young Rooney. John tells them to talk to him tomorrow, just talk.

Michael has seen his father when he comes home from work, and seen he has a gun, but he and his brother don't know what he does for a living, so the next day Michael stows away in the back of his father's car while he and mister Rooney go to see Finn. They arrive and go in, Sullivan with a tommy gun. Finn and Connor talk for awhile, and then as they start to leave, Finn gets mad about his brother, and 2 other men with shotguns enter the room. Connor shoots Finn and then Sullivan kills the other two men. Michael sees it all. Connor spots him, and Sullivan runs out and finds him. Sullivan tells him he can never speak of it again. Connor is nervous the boy will talk, but Sullivan tells him it's safe.

When they get home, Sullivan explains how they owe everything to the Rooneys, and that Michael can never speak of it, and Michael agrees, but he is still clearly shaken. Sullivan explains what happened to Annie, but says it'll be ok.

The next morning, John Rooney shows up after breakfast with the money from dice, but Michael barely sticks around. We then see a Rooney board meeting where Connor gets yelled at for killing Finn when it was just supposed to be talking. Sullivan is in the room. His job that night is to find people who are late repaying debts to Rooney. Connor gives him a letter from his father to give to tonight's debtor.

Sullivan arrives at a jazz club and at the mention of his name scares the bouncer. He meets with the wormy club owner and gives him the letter. The owner eyes him, then grabs for his gun. Sullivan gets it first and kills him and the bouncer. He looks at the letter and all it says is "Kill Sullivan and all debts are paid". He tries desperately to call home, but the phone is off the hook. Connor is there, and murders Annie and Peter in the bathroom. Michael was in detention for fighting. He is at the door when Connor starts to leave, and almost gets spotted.

When Sullivan gets home, Michael is sitting at the table, motionless. Sullivan goes upstairs and screams. Moments later they are leaving. Sullivan explains that it's not their home anymore, just an empty house, and he needs to go have a 'word' with Rooney.

He arrives at the house and gives Michael a gun, despite the fact he doesn't want it. Sullivan goes into Rooney's office and only finds a lawyer, who offers him a large sum of money if he'll just leave and go back to ireland. instead Sullivan asks him to give Rooney a message. He then shoots him in the head.

Sullivan comes back to the car and they start a drive to Chicago. Sullivan wants to see where Capone and Nitti stand on it. He sees Nitti and says he'll be willing to work exclusively for him if he looks the other way while he kills Rooney. Nitti says he can't, because the rooneys are too valuable, so Sullivan leaves. We then see that the Rooneys were hiding in a hidden room and heard the whole thing. Nitti convinces Rooney to hire a hitman, but Rooney doesn't want the boy hurt.

We see the hitman is a photographer named Harlen Maguire, played by Jude Law, who specializes in photographing the dead. He goes to the Sullivan funeral, and overhears when Sullivan calls his wife's sister and asks if he can go to her place in Perdition, Kansas after a while. Harlan tracks the call and eventually meets sullivan in a diner. Sullivan catches on, and slips out and slashes Harlan's tire. He comes out of the diner shooting, and Michael almost gets killed.

They pull over and Sullivan yells at Michael. He then explains that none of this is Michael's fault, regardless of what he thinks. He then explains he needs him for his new plan. The mob is guarding Connor because he's valuable to them, so what sullivan needs to do is make him less valuable, or even detrimental to them.

Sullivan knows that Capone keeps dirty money in banks throughout the tri-cities area, so he starts robbing them, taking only Capone's money from the bank manager, leaving some money for them. Michael is needed to be the getaway car driver, and eventually he gets pretty good at it.

After a bit, Capone withdraws all his money, but Sullivan tracks down an accountant for Rooney, and breaks into his hotel room to get something from him. It just so happens that Harlan was staying across the street, and saw him go in, so he throws on some clothes and follows him. Sullivan can't hear his son honking downstairs over the stock ticker in the accountant's room until right before Harlan bursts in shooting. Sullivan is able to duck behind a chest, and a firefight ensues, and eventually Sullivan shoots a lamp that sends glass flying into Harlan's face. Sullivan runs into the accountant's room where he lies dead, shot through the wall by Harlan, and Sullivan finds some folders, so he takes them all and runs out of the room. As he gets to the car, Harlan crawls to the window and shoots him in the shoulder. Sullivan tells michael to drive.

They finally stop at a farmhouse to fix his shoulder, and spend a few days there. The house is owned by an old couple who are very kind to them. Finally they leave, leaving a few bundles of money to thank them.

While at the farmhouse, Sullivan found some documents proving that Connor was stealing from his father, so he drives back home and finds old man Rooney at church, and they talk in the basement. Rooney says he knew his son was stealing from him, but would never just hand over his son to be killed. He again gives Sullivan a chance to walk away, but he refuses.

Sullivan decides it's time to end it. He guns down a group of John Rooney's bodyguards, finally leaving him and Rooney. John's final words are 'I'm glad it's you', and then Sullivan kills him. We then see Nitti on the phone with Sullivan. Capone has decided it's ok for Sullivan to kill Conner, as long as that's the end of it. Guards allow Sullivan up to Connor's room, and he shoots him in his bathroom.

The next morning he and michael leave for Perdition, for his aunt's beachhouse. While Michael runs on the beach playing with a dog, Sullivan goes up to the house and waves to him through a window. He is then shot twice by Harlan, who was sitting in the corner.

While Sullivan is lying on the floor dying, Harlin sets up his camera to take a picture, when Michael appears behind him with his gun.

Harlan advances on him telling him to drop the gun, and a shot is fired. Sullivan shot him, because Michael couldn't, and Harlan dies. Sullivan is glad that michael couldn't do it, and he dies. Michael drives back to the farmhouse where he narrates he grew up, though he lived a lifetime before that.

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