Plot:

Four lifelong friends from the Boston neighborhood of Charlestown—Doug MacRay, James “Jem” Coughlin, Albert “Gloansy” Magloan, and Desmond “Dez” Elden —rob a bank. They take the manager, Claire Keesey, hostage but release her without harm. Doug follows Claire to prevent Jem from eliminating her as a witness, but a romance grows between them which he hides from the gang. As they grow closer, Doug tells Claire of his search for his long-lost mother, and how he imagined she went to live with his aunt in Florida. He also blew a chance to be a professional hockey player for a life of crime. She tells Doug about seeing a tattoo on one of the robbers, and he realizes she can identify Jem and send them all to jail. He knows that Jem will kill her if he realizes the truth, and he persuades her that the authorities cannot protect her either so she decides not to tell the police. But Doug is increasingly disenchanted with his criminal lifestyle and the lies he has to tell.
FBI Special Agent Adam Frawley surveils the gang and recognizes their ties to local crime lord Fergus “Fergie” Colm, who has another robbery planned for them. During a visit to his father Stephen in prison, Doug reveals his plans to leave Charlestown and go to Florida. Stephen ends the visit by telling his son, “I’ll see you again, this side or the other.” The gang’s next robbery in the North End of Boston goes awry, and the gang barely escapes. Frawley interrogates the gang, but fails to get any confessions and is forced to release them. Doug asks Claire if she will go away with him, and she agrees. Grasping at straws, Frawley wiretaps Claire’s phone when he learns she quit her job and threatens to prosecute her as an accomplice after he realizes she is seeing Doug. Shocked to discover her lover was one of her assailants, she decides to help Frawley.
Meanwhile Fergie and Jem are pressuring Doug about the next job, but Doug is determined to get out despite all his old loyalties. Fergie finally threatens to kill Claire, and reveals to Doug how he controlled his father by making his mother an addict, which led to her suicide. Doug gives in, but swears he will kill Fergie if anything happens to Claire.
At Fenway Park, Doug and Jem enter disguised as Boston police officers, nab $3 million in cash, and prepare to escape in an ambulance disguised as paramedics. But Doug’s ex-girlfriend, Krista (who is also Jem’s sister), threatened by Frawley, reveals enough for the FBI to surround Fenway before the gang gets out. Caught in a firefight with S.W.A.T, Dez and Gloansy are killed, while Doug and Jem slip out in their police uniforms. Frawley spots Jem, and they exchange fire, but Jem is wounded and determined not to go back to prison (having served 9 years for a murder conviction), so he rushes the police and is gunned down. Doug sees it all but knows he cannot save Jem and walks away.
Knowing he’ll never escape as long as Fergie is alive, Doug kills Fergie and his bodyguard and calls Claire to ask her to come away with him to Florida. Watching from across the street, Doug sees the FBI is there as Claire tells him to come over, but eventually she gives him a cue to warn him away. Doug flees, donning an MBTA uniform and escaping from Boston by driving a bus. Later, Claire finds a bag buried by Doug in her community garden containing money, a tangerine and a note from him suggesting she can make better use of the money than he can, ending with, “I’ll see you again, this side or the other.” Claire donates the money, in memory of Doug’s mother, to refurbish the local ice hockey arena that Doug once played in. And from the deck of a small house, Doug looks out over the water, alone, seemingly safe in Florida.

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