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  • How come no one besides Frawley recognize Doug and Coughlin? Wasn't the only reason they showed up there because his ex-girlfriend had told the police they'd be there? You'd think more than one person would know just who exactly they're trying to get. His entire escape hinges on no one recognizing him.
    • The FBI only found out while the robbery was already under way. Frawley didn't have time to hand out photos to all the cops and FBI agents on scene. And hell, when they first arrived he thought that they might even have been too early or too late.
    • I don't quite buy it. Not one person asked "who the hell are we trying to catch anyway?" They did not have literally a second to send a text picture message? On the way over? Come on.
      • What, a failure of communication between Federal and local authorities during the course of a rapid deployment? That's impossible! We all know that there is absolutely zero jurisdictional conflict between the Boston Police Department and the FBI. It's not like we don't see any arguments or hostility between the two groups when they run into each other while clearing the stadium or anything. This kind of communications failure has happened before between agencies and/or local police. It even happens between municipal and county police, and even inter-precinct communications within a police department.
      • The trick is that Doug, Coughlin, Gloansy, and Dez switch disguises to pose as police officers and/or paramedics, i.e. exactly the kinds of people who are expected to be there. That is the reason why when wearing their cop uniforms in the parking garage, the FBI SWAT officers think Doug is just another cop in the crowd, and with the chaos of the scene, and the size of the Boston Police Department, neither the FBI or the real police officers are going to pay close enough attention to realize that the very men they're looking for are hiding amongst them. Not only that, but the radio communications at the start of the gunfight and the fact that Gloansy and Dez died wearing their paramedic uniforms, would lead the police to assume that Doug and Coughlin were still in their paramedic disguises. The police don't realize that Doug and Coughlin also had police uniforms on hand until they're able to get to the cash room, interview security, and learn that the robbers were disguised as cops when they stole the cash. Once Frawley overhears the police captain telling Dino this, he begins conducting sweeps of the area looking for any cops who are acting abnormally. Coughlin ends up being a dead giveaway as he's walking away from the action with one of the money bags over his shoulder. While the police are moving in on Coughlin after shooting him, Doug uses it as a distraction to steal a marked cruiser parked nearby, and Frawley doesn't pay much attention beyond a short glimpse (likely assuming that the police car was driving off searching for any other suspects).

  • How come no one thinks it's a bit fishy that Claire suddenly is wealthy and donates money to a hockey rink out of nowhere? You'd think the FBI would keep close tabs on her being that they're suspicious of her and have said as much in the movie.
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    • Both Doug and Claire have a connection to the rink. One is a bank robber and one is suspected of being his accomplice. A bunch of money just randomly coming from nowhere is always suspicious.
    • Also, the money was donated in the name of Doug's mother, and there was a placard at the rink stating that the gift was given in her memory. And Doug in question was a former professional hockey player, whose name was now undoubtedly all over the news, due to his crimes. The connection between the donation and the thief wouldn't be difficult to make.
    • Who said they didn't find it suspicious? The movie doesn't say either way what happened after Claire got the money except that there was an anonymous donation to the ice rink. For all we know the FBI did look into it but couldn't find any evidence connecting the donation to Doug or Claire beyond the name.
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    • Coming from a Bostonian, in all honesty no one would likely think twice of it and would just go with it. Remember this is the same city where Whitey Bulger came from (once again, this is coming from a Bostonian, I'm not trying to be offensive, just stating the facts).
    • Plus, it would be bad publicity for the FBI to shut down the hockey rink over this.
    • Also, the money was probably laundered: early in the theatrical cut, Frawley explains how the gang runs its money through casinos and drug buys so that it can't be traced back to them. The money that Doug leaves behind is from a stash he had, meaning it's quite possible that if it was tied to any of his heists it would have been tied to ones he pulled before he even met Claire.
    • There's also the whole 'anonymous' donation through a charity bit. Generally, the idea of an anonymous donation is that no one knows you're the one who's given it. Hence, the FBI might suspect it but not be able to prove it. Given it was named after Doug's mother, they're more likely to suspect he donated it, not her.

  • Finally, why, fucking why, does Claire love him? Stockholm Syndrome? The guy is not just a bank robber et cetera, but he gave her extreme trauma and made her emotionally needy... then went and had sex with her. It seems that she logically realizes this at one point. First, she says that her friends call him a rebound guy from the stress of the bank robbery. OK, then when she learns the truth she tells him "is this some weird sick thing you did" and asks why he would do something so terrible. He eventually apologizes and... she helps him escape and fools the FBI. HUH? So an "I'm sorry" covers what's some crazy mindfuck PTSD terror rape? That's a bit insane. Her help is what totally validates everything he did as ultimately correct... unless there's some alternate explanation where it just shows how emotionally damaged she was, but I doubt that given how the entire world of this movie is in love with Doug...

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    • People have fallen in love for even crazier reasons. And if it was Stockholm Syndrome then that still holds up in the context of the film and Claire's actions.
    • It's also worth remembering that for much of the movie, when Claire is actually falling in love with Doug, she doesn't actually know any of this, and falls for him because, from her point of view, he's a nice guy who's helping her get over a very traumatic situation. Even after learning the truth, her feelings towards him had to have been conflicted due to that; yeah, he did something very reprehensible, but then she saw something genuinely decent in him and perhaps thought that was worth redeeming him. 'A bit insane', maybe, but then again she's heavily traumatized, so we could technically argue that she is a 'bit insane'.
    • I can understand the love as a tragic product of sick, sick abuse of Stockholm Syndrome. But correct me if I'm wrong-it is intended to be a legitimate romance. We're supposed to want them to succeed. THAT is what REALLY bugs me.
      • No. It was never intended to be a conventional romance. The fact that it is between a bank robber and a former hostage, and ends badly between them once they find out, with Claire accusing Doug of abusing Stockholm Syndrome says as much. Also, it was completely consensual sex.

  • It just bugs me that Frawley instantly told Claire when she asked that only the guilty need lawyers. Is that the exact opposite of the truth?
    • It is the exact opposite of the truth. Everyone has a right to an attorney. However, it's almost always an interrogator's job to get people to waive Miranda, and in Frawley's case, he wanted to make sure he got every bit of information he could. What's more, considering the fact that she's a hostage who survived, the idea that she was an insider was not out of the question. So yeah, he relied on her lack of knowledge of the Constitution to get more information out of her. Immoral? Depends on how much you like cops. Illegal? Not by a longshot.
    • Also, Frawley says only the guilty need lawyers. In theory, innocence can be proven without one. In addition, as previously mentioned, he was trying to psych Claire out, should she have been a co-conspirator. Remember that when he discovered she was dating Doug, he said she did need a lawyer. So he's not immoral, he's just really good at his job. He never breaks or even bends laws or regulations. He's just ruthless.
    • Yeah, Frawley's just stating his own observations and opinions, not the truth. In his opinion, if you ask for a lawyer, you're guilty. That doesn't make it the truth.
    • Police officers have done and said much shadier things to get information out of suspects or reluctant witnesses. It is quite possible that, had they tried to use this conversation against her in a court of law, it would have been thrown out as she was being detained (although not arrested) and had not been read her Miranda rights.

  • During the final robbery, two of the robbers are dressed as cops, and are more or less staking their lives on their disguises, yet neither of them bother to shave? Their three day stubble-beards make the cop outfits look really suspicious.
    • ...Why?
    • Not really. It depends on the jurisdiction. Some enforce the dress code more than others.
    • They may have been figuring that you can shave after the heist to more rapidly change your appearance than to wait for a beard to grow. I dunno.
    • For most people, in a rather rushed and tense situation like that, you just see the uniform; you don't necessarily look closer unless you're given reason to, like Frawley got.
    • For what it's worth, the real Boston PD doesn't have a clean-shaven policy. Case-in-point, the famous Boston Bullpen cop
  • Where exactly did the movie pull that "300 bank robberies in Boston" statistic? That's ridiculously high even for the most crime ridden cities in the world.

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