Plot

Follows two robbers who must go on the run with the help of one of their therapists after a theft doesn't go as planned.

Rory (Matt Damon) and Cobby (Casey Affleck), who team up to rob a corrupt politician but end up in a chaotic escape after the heist goes wrong. Pursued by police and crime bosses, they enlist Rory's therapist (Hong Chau) to help them survive.—Oscar Serpa

In the upcoming night of Boston's mayoral election, corrupt incumbent Joseph Miccelli will organize a celebration at the Wharf, expecting massive amounts of cash bribes. Mobsters Besegai and Dechico plan to steal the money before it is picked up by armored car. They enlist their underling Scalvo, divorced Marine veteran Rory, and alcoholic ex-con Cobby Murphy. Rory is adamant that he receive a share of exactly $32,480. Rory struggles to explain his plans to his therapist, Dr. Rivera, while Cobby's bartender Mr. Kelly warns him not to return to his criminal ways.

The three sneak in through the kitchen, only to find the event full of people; challenger Mark Choi has won the election, but Miccelli refuses to concede. The Wharf's safe has already been emptied, so Scalvo robs Miccelli and his inner circle instead, taking Miccelli's bracelet. When the chief of police intervenes, he and Scalvo shoot each other dead and Cobby is wounded in the shoulder. He and Rory escape in the armored car, which they abandon. Laying low at Kelly's house, Rory and Cobby ask Dechico for help, but he sends Booch and Colani to kill them instead.

With a manhunt for the thieves underway, Miccelli tasks Frank Toomey of the Special Operations Unit to recover the bracelet, engraved with the combination to his office safe. Toomey questions Dechico, while Rory confides to Cobby that his share of the money is meant to make amends with his estranged son. Booch and Colani arrive to murder the two thieves, who have cut the house's gas line. Rory and Cobby escape with the bracelet as the house explodes.

Rory brings Cobby to Dr. Rivera, taking her as a willing hostage. They treat Cobby's gunshot wound, but are forced to flee in Rivera's car after she calls the police. Still determined to help Rory, Rivera joins them and they narrowly survive a high-speed police chase. Breaking into Mr. Kelly's empty bar, the three are confronted by Toomey, who leaves with Rivera and the bracelet. Surrounded by police, Cobby cuts the gas line again and escapes with Rory as the bar explodes.

Having memorized the combination, Cobby and Rory go to the mayor's office. Disguising as firefighters, they set off the fire alarms in the City Hall and sneak inside. They lock themselves in the mayor's office with his counsel, Alan Flynn. Unlocking Miccelli's safe, they discover millions of dollars in illicit cash, while Flynn offers to testify against Miccelli, giving them two hard drives with evidence of the mayor's misdeeds.

The police surround city hall and open fire, wounding Cobby in the same shoulder. Sent in to negotiate with the thieves, Rivera exits the building with Flynn, while Rory and Cobby push the safe out of the window, leading the crowd outside to scramble for the cash. In the chaos, Rory and Cobby escape in a fire truck, but are soon confronted by Toomey. They offer him the drives in exchange for letting them go free, but he takes them into custody.

Meanwhile, Besegai and Dechico escape to a cabin and attempt to reach the Canadian border on foot, while Miccelli is arrested. Choi takes office and is given the drives, which hold account information worth $100 million in untraceable funds. Realizing that he can keep the money for themselves as long as they don't indict Cobby and Rory, Choi lets them go. Rory reconnects with his son, while Cobby visits Rivera at home. In a mid-credits scene, Besegai and Dechico are found frozen to death in the wilderness.