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Plot
Four lifelong friends from Charlestown, Boston, Douglas "Doug" MacRay, James "Jem" Coughlin, Albert "Gloansy" MacGloan, and Desmond "Dez" Elden, rob a bank wearing masks. Against Doug's wishes, Jem takes a bank manager, Claire Keesey, hostage but later releases her unharmed. After finding out that Claire lives in their neighborhood, Doug follows her to find out how much she has told the police and to ensure that Jem does not eliminate Claire as a witness. Soon, a relationship grows between them, and Doug hides it from the gang. Claire, however, does not realize Doug is one of the robbers.
Doug tells Claire of his search for his long-lost mother, who he believes went to live with his aunt in Tangerine, Florida. He also talks about how he almost became a professional ice hockey player. Claire tells Doug that she saw a tattoo on one of the robbers' necks but did not inform the FBI; Doug realizes that she can identify Jem and send them all to prison. Doug knows that Jem will kill Claire if he knows, so to dissuade her from talking, Doug tells Claire that if she informs the police, they will put her in witness protection, thus sending Claire to live in another state. His plan works, and she remains silent.
FBI Special Agent Adam Frawley recognizes the gang's ties to local Irish mobster Fergus "Fergie" Colm, who moonlights as a florist. During a visit to his father, Stephen, in prison, Doug shares his plan to leave Boston for Florida. The gang's next job, an armored car robbery in the North End in which they disguise themselves as nuns, goes awry, and they barely escape. Frawley interrogates Doug and his associates but is forced to release them due to a lack of evidence and failing to get them to confess. Doug asks Claire to go away with him to Florida, and she accepts. Claire quits her job, unaware that Frawley has tapped her phone. He then shows his file on Doug to Claire, and threatens to prosecute her as an accomplice. Shocked and distraught that he was one of her assailants, Claire cooperates with the FBI and ends her relationship with Doug.
Doug tries to back his way out of an upcoming heist at Fenway Park, angering Jem who gets into a fight with him. Fergie then threatens to kill Claire if Doug does not cooperate, and he reveals to him how he controlled his father into doing his bidding by turning Doug's mother into an addict, which ultimately led to her committing suicide. Doug reluctantly agrees to do the job but swears that he will kill Fergie if anything happens to Claire. At Fenway Park, Doug and Jem enter disguised as Boston police officers, steal $3,500,000 in gate cash, and prepare to escape in an ambulance while disguised as paramedics.
The FBI, having been tipped off by Doug's ex-girlfriend and Jem's sister Krista, surround the perimeter alongside police and state troopers. Caught in a shootout with FBI SWAT agents, Dez and Gloansy are killed. Frawley spots Jem and they exchange gunfire in which Jem is wounded and forced to take cover. Determined to not go back to prison, Jem commits suicide by cop.
Knowing that Claire is in danger and that he will never escape as long as Fergie is alive, Doug kills both him and his bodyguard Rusty. After contacting Claire and watching from across the street, Doug spots the FBI with her; she is able to verbally warn him away. Doug then flees by donning an MBTA uniform from his uncle whom he leaves some money and later escapes by train. Meanwhile, Frawley deduces that Claire tipped Doug off, but is too cryptic to provide grounds for an arrest.
Later, while Claire is gardening, she finds a buried bag containing money, a tangerine, and a note from Doug that suggests that she can make better use of it and that they might see each other again one day. Claire donates the money, in memory of Doug's mother, to refurbish the local ice hockey arena where Doug once played. From the deck of a small house, Doug looks out over the water, forlorn, but seemingly safe in Florida.
Alternate ending
[edit]In the Alternative Cut, during his escape from Boston, Doug is confronted by the man he and Jem assaulted in defense of Claire. With two friends backing him up, he asks Doug where Jem is and where the money is (implying he knew about the heist, likely from Fergie). He and Doug argue with his partners encouraging him to kill Doug. The man is reluctant until Doug asks him, “How’s the leg?” at which point he shoots Doug several times in the street, leaving him to die. A later scene shows Claire, still with the money, seeing a news report of Doug’s death on TV.
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