The Town (2010)
As he plans his next job, a longtime thief tries to balance his feelings for a bank manager connected to one of his earlier heists, as well as the F.B.I. Agent looking to bring him and his crew down.
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.
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, doesn't know who they are. He contrives to meet her and then finds her appealing. As the FBI zeroes in on the gang, Doug wants out, Claire doesn't know who he really is, and 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?
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.
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.
- This synopsis is based on the extended edition of the movie available on the BluRay release. It is still being edited.
Text appears on the screen, stating "One blue-collar Boston neighborhood has produced more bank robbers and armored car thieves than anywhere in the world."
Testimonials from people acquainted with Charlestown then show up:
"Bank robbery became like a trade in Charlestown, passed down from father to son." - Federal Agent, Boston Robbery Task force
"I'm proud to be from Charlestown. It ruined my life, literally, but I'm proud." - Charlestown man, Boston Globe
It is early morning in Boston. In Harvard Square, a Cummins armored truck waits at the curb, its driver, Arthur Shea, sitting in the cab waiting for his partner Marty Maguire to come back. The voice of Doug MacRay (Ben Affleck) is heard telling his gang, comprised of his best friends James "Jem" Coughlin (Jeremy Renner), Albert "Gloansy" Magloan (Slaine), and Desmond "Dez" Elden (Owen Burke), all from the dangerous streets of Charlestown, the itinerary of the driver and the routine of his partner, who picks up money from the Cambridge Merchants Bank every Wednesday and Friday morning at 8:12 AM. Before going to work, Doug reminds Dez and Gloansy that they'll be screwed if a police helicopter or SWAT team show up, and if they see a police cruiser, to just shoot up the car's engine block and keep driving, so as not to injure any innocent people. Coughlin warns that the guards might try to test them.
In real time, Maguire walks from the truck to the front door of the bank, wheeling a dolly. Doug and his gang are waiting in a stolen city work van parked in front of the front doors, to cover their entrance. The moment the courier opens the door, the gang climbs out of the van, armed with submachine guns and wearing full face skeleton masks to hide their identities. A second after the courier enters the bank, the four gang members burst through the front doors and overpower him. Coughlin and Gloansy leap over the teller's desks, and subdue the tellers and guards. Gloansy empties a fish bowl filled with peppermints, and orders everyone present to place their cell phones in it. Everyone complies, and Gloansy then proceeds to fill the bowl with water. Coughlin then begins searching the drawers for money, careful to not take any wads with dye packs. While this happens, Des runs upstairs and begins disabling the security tapes. Doug secures the doors with a cable tie, then grabs assistant branch manager Claire Keesey (Rebecca Hall) and leads her over to the vault at gunpoint.
Doug and Coughlin train their weapons on Claire, and Doug asks her what the time lock is set for. She tells him it is set for 9:00 AM. He assures her it's not her money it is after. When the clock hits 8:15, Doug tells her "go" and she pretends to start to unlock the vault. Seeing Claire stalling, Coughlin trains his weapon on another employee and threatens to shoot him if she doesn't cooperate. Doug puts his hand on top of Claire's trembling hand and tells her to take her time. She slowly spins the combination, and the vault is unlocked.
While Doug enters the vault and begins loading the money into duffel bags, Des ejects the security tapes and puts them in a wastebasket. He then hauls them down to the breakroom and puts the tapes in the microwave, destroying them.
Back in the lobby, there is a knock at the door from a customer trying to get in, distracting Doug, Coughlin, and Gloansy. Claire, lying on her stomach, takes advantage of the distraction to use her foot to trip the silent alarm. Realizing that they have less time than they planned, Coughlin now proceeds to douse everything with a large jug of bleach. They prepare to depart, but are stopped when Dez tells them the silent alarm has been tripped. Coughlin flies into a fit of rage, demanding to know who set the alarm off. The bank president (Victor Garber) insists he hasn't touched it. Coughlin doesn't believe him and proceeds to whip him across the head multiple times with his submachine gun, and continues to do so until Doug stops him. As Doug is restraining Coughlin, Claire looks up and notices a distinct Fighting Irish tattoo of a man with a thief bag and pistol on the back of Coughlin's neck. The crew finish dousing every surface they can find with bleach. Coughlin takes notice of Claire and realizes she will be useful to them.
Once Doug finishes bleaching the vault, he comes out and immediately notices that Claire is missing. He then finds Coughlin and the others have taken her hostage, to use as a shield if the police show up. They lead her out the back door to a side alleyway, where they climb into a stolen electricians' work van. Gloansy takes the driver's seat while Doug, Dez, and Coughlin climb in back with Claire, wrists bound with cable ties. Once she is blindfolded, the gang remove their masks and Doug tells Claire she will be all right. They drive her to a beach near Logan International Airport, and let her out. Doug tells her not to remove her blindfold until she walks forward far enough to feel the surf on her toes.
As she reaches the water, the screen goes black and the words, "The Town," appear on the screen.
Back in Harvard Square, the crime scene investigation into the bank robbery is underway. FBI Special Agent Adam Frawley (Jon Hamm) and his partner Dino Ciampa (Titus Welliver) arrive to look at the scene. Dino notes that the robbers stole a city work van, which hasn't yet been reported stolen. He notes that the van was used to screen the front doors, and the robbers bleached the entire place to destroy all clothing fibers and any trace evidence of themselves. Examining the vault, Frawley observes that the robbers were careful not to take any of the bands of money fitted with dye packs and tracers. They are called away when Frawley receives a text on his BlackBerry, telling him that the getaway van has been discovered, and, almost as if expected, torched.
Indeed, the robbers have dumped the van on Medford Street in Charlestown, near the Tobin Memorial Bridge, and lit it on fire to destroy any evidence of themselves. When Frawley and Dino arrive at the scene, the fire department is just finishing putting out the blaze. Since all the professional robbers they know of are dead or in prison, the detectives conclude that they are dealing with a band of new professionals. Frawley is quick to determine that there likely are no eyewitnesses who may have seen the robbers.
Doug meets with Coughlin, Dez and Gloansy at an abandoned hockey rink. Coughlin tells them that they've got a little problem. He produces Claire's driver's license and tells them that she lives in the neighborhood, meaning that there's a chance she'll see them and recognize them. Coughlin proposes that they kill her and offers to take care of it. Doug snatches the license from Coughlin and asserts that he will take care of Claire, since Coughlin is responsible for their predicament and he will face prison time if he tries to intimidate a witness.
Simultaneously, Frawley is interviewing Claire at his office in One Beacon Street about her actions after she was taken hostage. She confirms that the men threatened to rape and kill her if she talked to the police, and took her driver's license, and that she did not try to escape. When asked by Frawley if she remembers any distinguishing marks on the four robbers, she doesn't bother to tell him about Coughlin's tattoo. Frawley observes that Claire's hands are trembling, and tells her that she is still suffering the residual effects from the events of the robbery. He assures her they are not inept cops.
Frawley explains to Claire that there were over 370 bank robberies in the city in the past year, more per capita than anywhere else in the world, but 98% of them come from a one square mile neighborhood called Charlestown. In fact, it is standard Boston Police Department procedure to close the Charlestown Bridge when they get word of an armored car robbery in the city. Bank robbery is a predominant trade in Charlestown, just like old European villages specialized in certain crafts for trade. Claire is shocked, as this is the neighborhood she lives in. Before releasing her, Frawley tells Claire she is being set up with a protective detail and hands her his business card. Claire takes one look at a photograph of a police blockade at the Charlestown Bridge. Her gaze then sees a surveillance photo on a bulletin board of a masked Doug and Coughlin holding her at gunpoint.
Doug and Coughlin go to Mike, one of their fences. While they are waiting, they converse on the couch. It is clear that Doug is disenchanted with his criminal lifestyle and wants out of it. They exchange some of the money for 100 pounds of marijuana. After selling the marijuana to another dealer, they go to Town Flowers to deliver a cut of the loot to local crime boss Fergus "Fergie" Colm, Following this, the gang goes to Mohegan Sun to gamble the money away.
Returning to Boston, Doug and the others head to a local bar. It is established that Doug is in rehab for alcoholism, since he has to drink juice when everyone else can drink regular beer. As he is getting juice at the counter, he is approached by his girlfriend, Coughlin's sister Krista (Blake Lively). It is clear as they converse that Krista is xenophobic, as they are talking about a fight she had with a Somalian woman and had two friends to help her out.
Doug dismisses himself and goes back to his apartment. He is in the middle of watching the drive-in movie theater shootout from Heat (1995) when Krista stops by to have sex with him. Later that night, when he finds himself unable to sleep, he uses a hockey stick to toss a puck in the air a few times.
The next day, after sitting through a boring Alcoholics Anonymous meeting, Doug goes to work tailing Claire. He observes her as she leaves her apartment and heads to a local Laundromat to wash her laundry. He sits down in front of one of the washing machines and pretends to read a newspaper, while keeping an eye on Claire. Doug gets lucky when she approaches him and asks him if he has any change she can use. He apologizes and claims he doesn't have any quarters for her. He then watches as Claire folds her clothes and begins to put them in a basket to take back to her apartment. As Doug watches, she stops upon finding a shirt that has blood droplets on it. Claire has a flashback as she recalls Coughlin beating her boss up with his gun, and recalls walking slowly along the beach after she was released. Noticing her starting to cry, Doug sees this as an opportunity to move in, and asks her if she is all right. He flirts with her and offers to buy her a drink to make up for the bad week she has been having and to make up for not having any quarters for her. He asks, "What's the worst that could happen?"
The scene cuts to Frawley and Dino raiding a crackhouse owned by a man named Henry. Though he attempts to escape, Frawley is able to eventually subdue him after a struggle, and discovers a pistol and illegal drugs. He asks Henry if he knows anything about the bank robbery. He admits that he knows these professionals disable the alarm for the vault by breaking into the junction box.
Meanwhile, Doug takes Claire out to dinner at a local restaurant owned by one of his former hockey friends. Doug reveals that he works for a local gravel company. Claire is intrigued by Doug's hockey roots and mentions that she volunteers at a local boy's and girls' club that would like to reutilize the ice rink (the one we saw Doug meet with the others in earlier) but the city of Boston has refused to give them money. She also wonders why a few of the neighborhood kids have been calling her a 'Tunie', and Doug explains that it's a term used to describe people who are not from Charlestown, originating in the 1990s to describe the fancy car radios which the rich folks brought to the neighborhood and which are stolen by the "native" residents. In spite of being attracted to Claire, Doug is forced to make up some lies about himself, for instance claiming that his father lives out in the suburbs (and by the 'suburbs', he means the Cedar Junction Penitentiary in Walpole). He also admits that he thinks his mother left and now lives down in Florida. Claire admits that she comes from Marblehead, where she represented the underclass because her family didn't own a boat (which is the item that determines your status in Marblehead). Doug assures her he has a friend who owns a boat and Doug suggests that they should continue their date there (though it's heavily implied that it's probably actually stolen).
During their moonlight boat ride, Claire questions Doug about bank robbers since he is from Charlestown and she recalls her interview with Frawley at the station. Doug admits that many things that people say about bank robbers in Charlestown are just exaggerations. He also says that back in the days many juveniles admired the bank robbers just as if they were rockstars, and wanted to emulate their idols. Doug, however, admits that he always just wanted to play hockey but was just not good enough to join a professional team.
Doug meets with Coughlin at a small diner the next day. Coughlin asks Doug what his progress is with Claire. He lies and says he's got nothing, and she doesn't need to be killed.
Frawley and Dino look at the junction box outside the bank as a Vericom utility crew works to patch it up. The supervisor notes that the way the crew hacked the box is so unique that the only way one could know how to do it is to get a job at Vericom. This leads the two agents to decide that at least one of the robbers might be a Vericom employee and may have called in sick on the day of the robbery. Frawley then meets with Claire at another restaurant to ask her some more questions over lunch. Claire asks Frawley if he thinks she is a suspect. He tells her that if he did, he wouldn't be questioning her over lunch. There's a quick distraction when Frawley's BlackBerry rings, having received a surveillance picture of a man holding up a credit union with a pistol.
Doug and Claire go on another date. While they're sitting in his truck outside her apartment, she talks about Doug's attack on her bank. As she talks, Doug learns that she's talked to the police, but he breathes a sigh of relief knowing that the police haven't yet identified him and his gang as responsible for the job. He also learns that David, the branch manager that Coughlin beat up, is in the hospital nearby and Claire feels terrible that she hasn't been able to see him since the robbery.
Doug and Claire go to Beth Israel Deaconess Medical Center to meet David. Doug is a bit hesitant due to the presence of a police officer guarding the door, but Claire assures him he will be okay. When they enter David's hospital room, Doug is aghast to notice that his entire forehead and right eye are wrapped in bandages from where Coughlin whipped him, and the doctors give David a 50% chance of the eyesight in his right eye returning. He is more depressed when he steps outside and talks with the police officer on guard duty about it.
Later, Doug and Claire are at a Dunkin' Donuts consuming drinks. Claire admits that she hasn't told the police about Coughlin's "Fighting Irish" tattoo, and she's afraid to tell Frawley this out of the possibility that she might be called to testify and her risk of getting killed will increase.
Later, while dropping Claire off, Doug asks about the Toyota Prius he saw her grab clothes from when he was surveying her, and Claire reveals it got vandalized by some neighborhood kids. She then reveals that there have been some other people who have been harassing her as she walks to work, throwing bottles and taunting her. Doug asks Claire if she recalls what they looked like.
Armed with a description of the men harassing Claire, Doug solicits help from Coughlin, though he doesn't tell Coughlin what the job is for. They approach another dealer and get an address for the two men. Doug and Coughlin pull up across the street from the residence in question, don hockey masks, then grab a baseball bat and make their way to the apartment. When they knock on the door, the tenant, Alex Colazzo, walks over to answer. As he opens the door, Doug and Coughlin barge in and begin beating him and his friend up. While Doug controls himself, Coughlin is more vicious, striking his hand with a hammer and smashing a beer bottle over his head. Lastly, Coughlin shoots Colazzo once in each leg. Doug scatters some packs of cocaine dust around to make it look like a drug deal gone wrong, and he and Coughlin depart, unnoticed by the responding cops, who are rolling dark as they respond to what they think is a domestic disturbance.
The police begin to narrow in on the gang when they identify Desmond Elden, who works for Vericom as a systems tech operator. Even though he does not have a criminal record, Dino explains to Frawley that most bank robbers in Charlestown have no-show jobs. They will carry out a job, and when the police question the foreman, he will tell them the guy was present and show them a forged timecard. Fortunately for the cops, Vericom does not do such a practice because they are a public company, meaning that failure to show up at work is recorded as a sick day, and Des has recorded several sick days that "coincidentally" fell on the same days as a number of recent armed robberies of either banks or armored cars. Frawley and Dino tail Des and take several surveillance photographs of him with Doug, Gloansy and Coughlin at a barbecue. They produce their photos and brief their colleagues on their other three suspects:
-Gloansy is a notorious car thief, who has never met a car he couldn't boost. He's the kind of man who can start your Cherokee for you while you're still looking for your keys (overlaid with footage of Gloansy breaking into a Jeep Grand Cherokee in a parking lot).
-Coughlin has a troubled life. His father was murdered in prison, and his mother died of HIV. When he was 18, he shot a boy dead in a cemetery. When asked by the judge why he did it, he said he didn't like the kid, and ultimately served nine years for manslaughter.
-Doug is the suspected architect. He used to date Coughlin's sister Krista, who most likely mules to "the Florist" (Fergie), who formerly employed Doug's father Stephen MacRay. He also did a year and a half in prison for robbing a BayBank with a nail gun after he washed out from pro hockey. He apparently had been the real deal, and got drafted, but got kicked out when he started fighting with the guys on his own team. It is here that we learn more about what Doug's father is in prison for: in 1995, he hijacked a bread truck (armored truck) up to Nashwood, New Hampshire. When one guard saw his face, he executed both of them with their own weapons. Frawley notes that this consequentially led to new rules saying that an armored car driver is not allowed to leave the cab even if his partner is being held at gunpoint.
Doug is next seen having lunch with Claire at an outdoor café not far from the bank. He's stunned her friends are not jealous of her for dating him. He notices an odd look on Claire's face and learns that she had a brother of died of lymphoma on a sunny day like this, and she finds it wrong to think about death whenever it is sunny outside. When Claire excuses herself to use the bathroom, Coughlin shows up to confront Doug. He is still there when Claire gets back, forcing Doug to use his hand to cover Coughlin's neck tattoo and improvise a story. After some tense conversation, Coughlin leaves.
Doug confronts Coughlin later for stalking him and Claire. Coughlin defends himself by arguing that Doug is endangering them by sleeping with the one person who could give them to the police. Doug also doesn't like the next planned assignment - an armored car robbery in the North End. Doug doesn't like the fact that there is a guard assigned to the vehicle that acts like he's G.I. Joe. Doug finally agrees to do it, on the condition that this be their last job for a while.
Doug next pays a visit to his father at the Cedar Junction Penitentiary. Doug talks about how he wants to leave his criminal life, to which his father advises him "Either you got heat or you don't."
That night, Doug has sex with Claire. The next morning, he leads the gang as they carry out a blitz attack on an armored car in the North End. Before leaving their base, they grab some shaved hair from a barbershop. The four shower and scrub themselves vigorously, to get rid of any loose skin that could get on their clothes and leave DNA for the police to track them. As they load their weapons, they not only wipe down and polish the weapons themselves, but they also wipe down every single bullet that they load into each clip.
Once they are ready, Doug, Coughlin and Gloansy pile into a Dodge Grand Caravan, throw some filled gasoline jugs in the back, and drive to the North End, with Gloansy driving.
As Doug, Coughlin and Gloansy arrive at the ambush location, outside a bank at the corner of Parmenter and Salem Streets, they find that the armored truck is running late. They are forced to circle once around the block while they wait, to avoid suspicion. As they complete their first go-around, they see the armored truck pull up to the curb. Gloansy tells Doug and Coughlin, "Say your prayers. Here we go." All three men proceed to don rubber masks, complete with wrinkled faces and nun's veils. Doug looks out the window, and a young boy on the sidewalk locks eyes with Doug, horrified at the appearance of a submachine gun wielding "nun".
In real time, Gloansy speeds up, blows through a crosswalk, rounds the corner, and screeches to a halt alongside the armored truck. Even before he has brought the van to a stop, the left passenger door flies open and Doug and Coughlin jump out. The guard on the sidewalk instinctively grabs for his pistol, but Doug disarms him with the barrel of his submachine gun. Meanwhile, Coughlin rushes up and overpowers the guard in the back of the truck, then proceeds to break open the cabinets protecting the money. Doug shoves the bags on the dolly over to the van and begins watching the street for police, while Coughlin loads the money he can grab into a satchel.
There is a pause when Gloansy hears the distress call about the robbery going out on his police scanner. He yells this to Doug and Coughlin, indicating that they need to finish up. Coughlin looks up and notices that the truck driver has left his seat. He turns around and sees that the driver has taken Doug hostage and is holding a pistol to his back. Doug urges the driver to calm down and let him go. The driver doesn't move until Coughlin appears with his carbine and fires a burst, hitting the driver in the chest. He survives, though, thanks to his bulletproof vest. Doug and Coughlin hurriedly jump into the back of the van with their money and they speed off.
As they drive off, Doug tells Gloansy to drive slow and act normal. However, just as they are going around a corner a few blocks away from the scene, Doug looks behind them and sees a police car. Just as he recognizes it, the police car immediately turns on its siren and gives chase. Gloansy punches the gas pedal all the way to the floor, and makes several quick turns, trying to shake off their pursuers, and inadvertently causing a couple of small pileups as other vehicles try to get out of the way. As they are making another right turn at a three-way intersection, a second police car driving on another street notices them, stops, then backs up and turns onto the street they are on right behind the first police car.
Gloansy continues to gain speed, trying to outrun the cops. The first police car gains on them, and as they enter a three way intersection, it proceeds to carry out a PIT maneuver. It pulls up alongside the van, and then it forcibly swerves into the side of the van's rear bumper. Gloansy is unable to maintain control, and the van spins around and screeches to a stop.
The two police cars come to a halt in front of the van. The officer in the first cruiser gets on his microphone and orders them out of the car. When they don't act right away, he repeats his command. Suddenly, Coughlin raises his carbine and fires a burst through the front windshield. Bullets pound the forward unit and the officer driving the car jumps out, crawling away under heavy gunfire. While Coughlin is firing, they hear more sirens and another police car screeches a stop, cutting them off from the other direction. Doug opens his door, leans across the roof, and opens fire on the police car, riddling its engine block with bullets. The officer in the third police car jumps out, draws his pistol and fires two rounds at Doug, before he is forced to take cover. Coughlin and Doug fire further suppressive bursts on the police as Gloansy backs the minivan up past the third police car to another cross street, then makes a hard left turn and speeds off. The second police car to arrive quickly speeds off in hot pursuit.
Gloansy continues to barrel through the streets at high speed, rounding the corners as the three men struggle to shake off the pursuing police car. With a long and straight stretch of open road in front of them, Gloansy accelerates to full speed, as they speed towards the switch point. Reaching another cross street, the gang almost loses control when another police car pulls off a side street at high speed and rams them from the left side around their front headlight, trying to force them off the road. The two cars trade paint for a few hundred feet, during which the van's left front hubcap breaks off, until the next intersection, where Gloansy is able to make a right hand turn while this police car brakes to avoid a collision with a guardrail, then gets t-boned by another motorist.
Still being tailed by the other police car, Gloansy makes several tight turns through the narrow streets until he makes a right hand turn onto Foster Street. Halfway down the block, a stolen Jeep Grand Cherokee driven by Des pulls out of the lot and stops in front of them. Gloansy brakes to a stop, and the police cars chasing them come to a stop behind them. The three men in the minivan promptly climb out. The officers simultaneously climb out of their cars, pistols in hand. Before they can shoot, Coughlin raises his rifle and opens fire, riddling their cars with bullets and sending them diving for cover. While Coughlin keeps the police officers pinned down, Doug grabs the money bags and douses the interior of the car with the gasoline jugs. He then tosses a lit cigarette lighter into the car. The police officers instinctively run, just as the gasoline ignites, causing the interior of the minivan to explode in a ball of flames. Doug and the gang jump into the Jeep and peel away, tires screeching.
The Jeep bursts out onto Commercial Street. Gloansy drives recklessly through traffic as he turns left and begins driving in the direction of the Charlestown Bridge. Just then, the other crew members overhear a dispatcher sending several police units to the north end of the bridge to block it. Gloansy immediately presses his pedal to the floor and is soon hitting in excess of 80 mph as he weaves through traffic, even driving against the flow trying to get there in time. They reach the bridge, and after a few maneuvers to navigate around traffic moving through the intersection, they turn right on Washington Street and roar across the bridge. They are already halfway cross the bridge and long gone by the time the police arrive.
Gloansy drives the car back to Charlestown, untouched, and parks it on Tufts Street at O'Reilly Way. Doug and the gang jump out, Coughlin planting the hair we saw being acquired from the barbershop earlier in the backseat. They have only just started preparing to transfer everything to their second switch car when they see something that stops them dead in their tracks: a police officer is sitting in his car parked directly across the street from them, and staring at them. The four armed robbers stare tensely at the officer, who stares back at them as both parties wonder what to do. After a few tense moments, the standoff is broken when officer turns his head away from them as if to look at some utility workers working nearby. Doug, Gloansy, Dez, and Coughlin finish transferring everything to a Ford Taurus stationwagon and drive off, the officer deciding it wiser not to chase them. In the stationwagon, Coughlin quips the officer didn't want his name on the VFW memorial wall.
Frawley and Dino are next seen looking at the burned out remains of the minivan. Frawley is agitated, as there isn't enough evidence at any of the scenes to secure a conviction, so he orders the police to round up the suspects for questioning.
The next day, the police round up the four men and take them to the police station to be photographed and interrogated. Unfortunately for Frawley, his suspects are much smarter than he thinks they are. Frawley attempts to question Coughlin, who merely says "Lawyer!" Frawley leaves without saying another word. Doug and Gloansy each are told to read some lines from a transcript of a witness statement, to mixed results: Doug mumbles his way through the lines, while Gloansy reads the first few lines before acting like he can't read them.
Doug is brought to an interrogation room. He recognizes Dino, having apparently had run ins with him in Charlestown before. When Frawley enters to interrogate Doug, he makes it absolutely clear there is little chance of him getting a reduced sentence by testifying against his accomplices. But Doug proves too smart for Frawley, and he is forced to release the four. Frawley leaves Doug with a warning that he will do whatever it takes to make a charge stick, and will then tell Doug to 'go fuck himself.'
Jem approaches Doug with another job, but he turns it down. He tells Fergie he will not do the job, but Fergie reveals that Doug's mother never left the family. She committed suicide after Fergie got her addicted to drugs in retaliation for Doug's father attempting to also leave and warns that he will kill Claire if Doug does not do the job. Doug finally agrees.
The job starts Doug and Jem enter Fenway Park dressed as Boston police officers, wearing sunglasses to hide their identitites, while Dez deactivates the security system. Doug and Jem approach the guards near the cash room and pretend to be responding to a 911 call, then draw pistols on the guards and force them to the ground, zip-tying their hands behind their backs. They then threaten the men in the cash room to get him to let them in. After securing these men, they load $3 million into their duffel bags and head over to their getaway vehicle, an ambulance parked in the garage, where they meet Gloansy and Dez and change into paramedic uniforms. Unfortunately, they sense that it is too quiet, look outside, and see that the police are taking up positions outside. When Jem spots an FBI SWAT team in the garage, he opens fire on them. A shootout erupts, and in the process, several SWAT officers in the garage are wounded, and Dez is killed when he is deafened by a flash grenade (Doug, Jem and Gloansy cover their ears) and then shot by a SWAT officer. Gloansy offers to sacrifice himself to protect Doug and Jem, gets into the ambulance, and bursts out of the parking garage. The police fire on the van, hitting Gloansy at least twice, and the ambulance crashes into a mobile command center. As the cops move in on the ambulance, Doug and Jem in the garage put on their cop uniforms, blending in with the BPD officers moving in, and they go separate ways.
Frawley figures out the ruse when he overhears a police captain talking to Dino about how the robbery was committed by two cops. He scans the officers on the scene, then he and Dino drive slowly through the area near Fenway Park, spotting one cop walking away from the action carrying a duffel bag. They realize it is "Officer" Coughlin. Frawley immediately gets out of his car and follows Coughlin into a parking lot, just as Doug emerges out a door nearby. Frawley tries to get Coughlin's attention, but Coughlin does not respond until Frawley addresses him by name. On cue, Coughlin turns around, a TEC-9 automatic in his hand, and opens fire on Frawley. Frawley dives for cover as Coughlin chases him around a parked car, riddling the car with bullets. After pinning Frawley down, Coughlin runs off. Frawley gets to his feet and fires a single blast with his shotgun, before running after Coughlin.
As Coughlin reaches Boylston Street, multiple police cars screech to a halt from both directions. Doug reaches the sidewalk and can only watch what happens next. The moment the responding BPD cruisers come to a stop, Coughlin immediately opens fire on them. Several officers jump out and begin shooting back with their pistols. In the vicious exchange of gunfire, at least two officers get shot (although whether they survived or not is never mentioned). There is a brief delay when Frawley's aim is obstructed by a passing motorist trying to get past the police cars blocking the road. Once the car clears, one police officer breaks cover, aims his pistol, and shoots Coughlin in the chest. Coughlin falls, unharmed due to his bulletproof vest, and fires several more bursts in both directions. He then tries to run, but Frawley takes aim with his shotgun and fires twice. The first blast shatters the glass on a newspaper vending machine, while the second blast hits Coughlin in the back of his leg and knocks him down. He crawls back behind a mailbox to ponder his options.
More police, backed up by the FBI SWAT team, arrive and train their weapons on the mailbox Coughlin is hiding behind. Frawley yells for Coughlin to surrender. Coughlin then empties his Glock pistols at a police car, raking it with bullets. Frawley gives Coughlin 30 seconds to comply. Coughlin takes the opportunity to enjoy a discarded soda left on the sidewalk. He then yells that he surrenders, and stands up, raising his now emptied TEC-9s. A SWAT officer almost immediately shoots him through the head. As Coughlin's body is blown backwards against a telephone pole, multiple cops proceed to empty their pistols into him, and he falls to the ground, dead. While Frawley and a few uniformed cops approach the fallen Coughlin with their weapons drawn, Doug quietly climbs into a police car and drives off, unnoticed amidst the chaos.
Doug drives the BPD unit over to Fergie's shop. Upon entering, he tells Rusty, Fergie's bodyguard, that something's gone wrong, then puts his pistol to the side of Rusty's head and blows his head off. He then seeks out Fergie, who begins shooting at him with a pistol. After an exchange of fire, Fergie falls, badly wounded. Doug walks up to Fergie, puts his pistol to Fergie's testicles, and asks him, "Remember, who clipped your nuts for ya?" The screen cuts to black with the sound of a gunshot.
He calls Claire and asks her to come away with him, but he is watching from a house nearby 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 then Doug says he will come to the back door in an hour, Claire says she wants to meet him as it will be just like one of her sunny days, a reference to an earlier conversation when she said her brother died on a sunny day, meaning it's a coded message to warn him that the FBI are there. Doug puts on an MBTA bus driver's uniform, makes his way to an Amtrak station, and boards a train heading south. Frawley waits with his men, but knows Doug isn't going to show up. As Frawley is leaving, he figures out the code phrase that Claire used to warn Doug away, and tells her that he has jurisdiction all around the country to pursue Doug wherever he flees. Frawley returns to his car to find a note from Doug tucked under the windshield: "Go fuck yourself."
Later, Claire finds a bag buried in a community garden which she tends. 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 the renovation of a local hockey rink, and dedicates it to Doug's mother.