
Four lifelong friends—Doug MacRay (Ben Affleck), James “Jem” Coughlin (Jeremy Renner), Albert “Gloansy” Magloan (Slaine), and Desmond “Dez” Elden (Owen Burke), from the dangerous streets of Charlestown, a neighborhood in Boston, Massachusetts—rob a Cambridge bank, taking bank manager Claire Keesey (Rebecca Hall) hostage. After Claire’s release, Doug follows her and they begin a relationship. He explains that his mother deserted him as a child and apparently moved to Tangerine, Florida. He also describes his father’s subsequent emotional reaction and depression, but omits mentioning that his father is currently an inmate in a state prison in Massachusetts, convicted of armed robbery and murder.
FBI agent Adam Frawley (Jon Hamm) surveils the crew of MacRay, Coughlin, Magloan and Elden and realizes they work for “Fergie” Colm (Pete Postlethwaite), a local florist. Doug is hesitant to undertake their next assignment, and his fears are confirmed during the robbery in the North End, where gunfire erupts. The police arrive quickly, a chase ensues, and the team barely escapes. Frawley then arrests the four of them and interrogates each of them, hoping to get a confession, but fails. Frawley learns of Doug and Claire’s relationship through a recorded phone conversation and confronts her about the suspects. Claire is shocked to learn that Doug is a suspect, but Frawley believes she is an accomplice because of her relationship with Doug.
During a visit to his father (Chris Cooper) at the local state prison, Doug reveals his plan to leave Charlestown. Jem approaches Doug with another job, but turns it down. Doug tells Fergie he will not do the job, but Fergie reveals that Doug’s mother never left the family; instead, she committed suicide after Fergie got her addicted to drugs in retaliation for Doug’s father attempting to also leave Fergie’s employ. Fergie tells Doug he will kill Claire if he doesn’t agree to the job, so Doug agrees, but threatens to kill him if he even suspects Fergie will harm Claire.
The job is at Fenway Park. Doug and Jem enter dressed as Boston police officers, trick the guards and counting room staff, steal millions of dollars, and prepare to leave in an ambulance dressed as paramedics. Krista (Blake Lively), Jem’s sister and Doug’s one-time lover, snitches to Frawley, so the FBI surrounds the building. Jem spots SWAT officers and begins to shoot. In the firefight, Dez is killed. Gloansy creates a diversion and is killed while Doug and Jem put their cop uniforms back on and slip out. Agent Frawley figures out the ruse, catches sight of Jem, and tries to arrest him. Jem fires at Frawley and tries to escape, but he is cornered by the police. He has a shootout with the police in the middle of the street, and manages to shoot a few of the officers before being wounded in the leg by a blast from Frawley’s shotgun. Knowing there is no way out, Jem chooses to let the police kill him in suicide by cop fashion, rather than go to prison.
Doug escapes in a police cruiser, heads to Town Flowers, killing both Fergie and his bodyguard. He calls Claire and asks her to come away with him, but he is watching from his uncle’s apartment across the street and can see the FBI are in the same room with her. Claire, at first tells him to come to the room to pick her up, but in the end gives him a coded message to warn him to stay away. Doug takes an MBTA uniform from his uncle’s closet and escapes from Boston. Later, Claire finds a bag buried in a community garden. The bag contains money, a tangerine, and a note that ends with “I’ll see you again, on this side or the other.” Claire uses the money to finance a renovation of a local hockey rink, and dedicates it to Doug’s mother.
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