Plot

A proficient group of thieves rob a bank and hold the manager hostage. Things begin to get complicated when one of the crew members falls in love with her.

The Charlestown neighborhood of Boston is renowned for churning out a high number of armed robbers, generation after generation. These robbers never leave their Charlestown life on their own volition, the neighborhood where there is an unwritten code to protect that lifestyle. Such robbers include friends Doug MacRay, James Coughlin, Albert 'Gloansy' Magloan and Desmond Elden. Doug and James in particular treat each other like family, as the Coughlins have realistically been as such to Doug since Doug's mother ran off and Doug's father, Stephen MacRay, was sent to prison. James' single mother sister, the drugged out Krista Coughlin, and Doug have a casual sexual relationship. The foursome carry out a mostly successful bank robbery, but due to circumstances take the bank manager, Claire Keesey, hostage for a short period before releasing her physically unharmed. They find out that Claire lives in Charlestown, so they want to ensure that she did not see anything that could incriminate them if they were to ever run into her. As such, Doug begins a personal relationship with her to find out what she knows and what she's told the police and the FBI, who have taken charge of the investigation. He learns that she has kept some information from the authorities for her own protection but information that could identify James in particular. But Doug slowly falls for her, as she does for him. Ultimately, Doug dreams about leaving his Charlestown life to be with Claire anywhere but there. But Doug has to try and keep his true identity from her, and keep the fact that he is seeing her from his colleagues. But leaving is not as easy as he would like as he and the gang are tasked with a big job by a local gangster named Fergie whether Doug likes it or not. And Adam Frawley, the FBI's lead investigator, comes into evidence that links the foursome to the bank robbery and a subsequent armored car heist, so is on their tail for evidence that will send them away dead or alive.—Huggo

In Boston's bleak Charlestown, criminals depend on a code of silence: those caught serve their time. Doug MacRay masterminds bank robberies with three friends: the hotheaded Jem; Des, an electrician; and Al, their driver. After a dicey bank job, Doug must make sure the female bank manager, Claire, who lives in Charlestown, hasn't recognized any of the crew. He contrives to meet her, finds out she doesn't know any of the crew and, in the process, finds her appealing. As the FBI zeroes in on the gang, Doug wants out of the crew, but Jem and their money launderer, an aging florist, insist that Doug do one more job. Are prison and death the only ways out of Charlestown?—<jhailey@hotmail.com>

After the heist of the Cambridge Merchants Bank, the four thieves blindfold and kidnap the manager Claire Keesey. They take her driver license; release her at an empty beach; and head to Charlestown, Boston. Later, the friends Doug MacRay, James Coughlin, Albert 'Gloansy' Magloan and Desmond Elden find that Claire also lives in Charlestown and they decide to monitor her steps. Doug MacRay gets close to Claire to know what she might have told to the FBI and they fall in love with each other. Meanwhile, the FBI Special Agent Adam Frawley is assigned to investigate the heists to armored trucks and banks in Charlestown and he concludes that the thieves are the four friends. He joins his team and keeps Doug and his friends under surveillance. Doug decides to move to Florida with Claire and begin a new life; however, the dwellers are trapped in Charlestown and they do not have any way out but dead.—Claudio Carvalho, Rio de Janeiro, Brazil

The son of a tough Charlestown, MA thief, Doug passed on his chance to walk the straight and narrow in favor of becoming a career bank robber. Not only is Doug's crew one of the most ruthless in Boston, but they're also one of the best; they never leave a trace of evidence, and always make a clean break. Over the years, Doug's fearless partners in crime have become something of a surrogate family to him; Jem (Jeremy Renner), the most dangerous of the bunch, is the closest thing Doug has ever had to a brother. But a divide begins to open between the two career criminals when Jem takes bank manager Claire Keesey (Rebecca Hall) hostage during a particularly tense heist, and the group subsequently discovers that she hails from their own tight-knit suburb. When Jem proposes that the gang make an effort to find out just how much Claire recalls about the crime, Doug fears that his volatile partner may do more harm than good and volunteers himself for the job. Later, Doug turns on the charm while pretending to bump into Claire by chance, and becomes convinced that she doesn't suspect him of being the same man who just robbed her bank. As the feds turn up the heat on the gang, Doug finds himself falling for Claire, and searching desperately for a means of cutting his ties to his criminal past. But with each passing day, Jem grows increasingly suspicious of Doug's true motivations. Now caught between two worlds with no chance of turning back, Doug realizes that his only hope for finding a happy future is to betray the only family he's ever known.

One Boston Neighborhood Charlestown has produced more bank robbers and armored car thieves than anywhere else in the world. Four lifelong friends from the Boston neighborhood of Charlestown, Douglas "Doug" MacRay (Ben Affleck), James "Jem" Coughlin (Jeremy Renner), Albert "Gloansy" MacGloan (Slaine), and Desmond "Dez" Elden (Owen Burke), rob a bank. They take the manager, Claire Keesey (Rebecca Hall), hostage, but release her unharmed. When they find out Claire lives in their neighborhood, Doug begins to follow her to find out how much she has told the police, and to make sure that Jem does not eliminate her as a witness. Soon a romance grows between them, which Doug hides from the gang.

As they grow closer, 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 recounts his chance to be a professional hockey player which he threw away for a life of crime, following in his father's footsteps. She in turn tells Doug that she saw a tattoo on one of the robbers, and he realizes that she can identify Jem and send them all to jail. He knows that Jem will kill her if he discovers the truth, so he persuades her that the authorities cannot protect her, and she decides not to tell the police.

After Claire tells Doug about being harassed and her car vandalized by Alex (Isaac Bordoy), a local Dominican thug, Doug enlists Jem for a favor, which they can never talk about. Doug and Jem don hockey masks and violently assault the offenders without Jem knowing the true reason for the favor is to protect Claire.

FBI Agent Adam Frawley (Jon Hamm) surveys the gang (he figures out that one of the gang members had innate knowledge of Telecom equipment, so when he looks at the list of all Telecom employees in Charlestown, he finds the profile of Desmond, who had taken 4 sick leaves which matched perfectly with the dates of major bank robberies in the Boston area) and recognizes their ties to local crime lord Fergus "Fergie" Colm (Pete Postlethwaite), who has another robbery planned for them. Fergie finds out that Doug is dating Claire.

During a visit to his father Stephen (Chris Cooper) in prison, Doug reveals his plans to leave Boston and go to Florida. The gang's next robbery in the North End goes awry, and the gang barely escapes. The gang is interrogated by Frawley, but he fails to get any confessions and is forced to release them. Doug asks Claire if she will go away with him, and she agrees. When Frawley learns that Claire quit her job, he wiretaps her phone and threatens to prosecute her as an accomplice after realizing that she is seeing Doug. Shocked to discover that her lover was one of her assailants, she is forced to cooperate with the FBI and breaks up with Doug. Meanwhile, Fergie and Jem are pressuring Doug about the next heist, but Doug is determined to get out. Fergie threatens to kill Claire if Doug does not go through with the job, and reveals to Doug how he controlled his father by making his mother an addict, which led to her suicide (Till Fergie told Doug, Doug believed that his mother walked out the door and left him, but in reality, she committed a drug induced suicide). Doug gives in 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, disguised as paramedics. Krista (Blake Lively), Doug's ex-girlfriend and Jem's sister, threatened by Frawley and heartbroken by Doug's going away without her, reveals enough for the FBI to surround Fenway before the gang can get out (Krista is especially angry when Frawley tells her all the gifts Doug got Claire, while he never got Krista anything even after being with her for years). The gang is caught in a firefight with FBI SWAT operators, and Dez and Gloansy are killed.

Frawley spots Jem and they exchange gunfire. Jem, determined not to go back to prison and out of ammunition, commits suicide by cop by running out of cover with his guns unloaded and is killed. Knowing that Claire is in danger and that he will never escape as long as Fergie is alive, Doug murders Fergie and his bodyguard and calls Claire. Watching from across the street via binoculars, Doug sees that the FBI are with her as she tells him to come over. He at first thinks she means to betray him, but eventually she gives him a clue to warn him away, which he picks up on.

Doug flees instead, donning an MBTA uniform and escaping on a train. He leaves a note on Frawley's car, reading "GO F**K YOURSELF". Later, while gardening, Claire finds a buried bag containing the stolen money, a tangerine, and a note from Doug, suggesting that she can make better use of the money than he can, and that they might see each other again. 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.