Douglas "Doug" MacRay
The leader of the crew.
- Affably Evil: Though he robs banks and takes hostages, he's surprisingly nice so long as his victims cooperate and everything goes fine.
- I Coulda Been a Contender!: He had a chance to become a professional hockey player, but threw it away to become a criminal like his father.
- The Leader: Of the gang.
- Missing Mom: His mother disappeared when he was young, leading him to believe she ran off to Florida. Fergie later reveals she committed suicide.
- Noble Demon: Although he's a bank robber, he at least tries to keep his jobs clean and avoid unnecessary violence.
- Sole Survivor: In the theatrical cut, he's the only member of the crew to survive the Fenway Park robbery and get away.
- Red Oni, Blue Oni: To Jem. Both of them have similar backgrounds, but Doug is significantly calmer, while Jem is quick to resort to violence
- Villain Protagonist: He's a bank robber, so this is a given.
James "Jem" Coughlin
Doug's childhood friend, and second-in-command.
- Ax-Crazy: He's quick to resort to violence, as seen when he beats up the branch manager in the opening robbery.
- Best Friends-in-Law: Doug has been in an on-off relationship with Jem's sister, Krista. Jem is supportive of it, though Doug is only in it for casual sex.
- Dark and Troubled Past: His father died in prison, and his mother, from HIV, and at the time of the film, he recently got out of nine years in prison for manslaughter.
- The Lancer: To Doug.
- Never Going Back to Prison: Part of his reason for his Suicide by Cop at the end of the film.
- Pet the Dog: It's revealed that the shot the kid nine years ago in order to protect Doug, as the kid planned on killing him.
- Suicide by Cop: Surrounded by cops and determined not to go back to prison, he chooses to charge them with empty guns, getting himself killed.
Desmond "Dez" Elden
The gang's technician.
- Boom, Headshot!: How he goes out in the final fight.
- Demoted to Extra: He has an actual backstory in the original novel, but doesn't have any major role in the film beyond providing a link Frawley needs to identify the gang.
- The Smart Guy: He works for Vericom as a systems tech operator, explaining how he understands the banks' security systems.
Albert "Gloansy" MacGloan
The gang's getaway driver.
- Badass Driver: He handles himself really well in Boston's narrow streets.
- The Driver: He's responsible for securing rides and driving the gang away once their jobs are done.
- Drives Like Crazy: He ends up causing a lot of accidents during the botched North End robbery.
- Heroic Sacrifice: Offers to distract the police by driving out, allowing Doug and Jem to get away. He gets killed in the process.
- Anti-Hero: He's ruthless in his pursuit of the gang.
- Cowboy Cop: Subverted. Frawley may seem like a very dark take on this, but nothing he does violates the law or standard police protocol. He's simply ruthlessly efficient and willing to do whatever's allowed to do his job.
- Good Is Not Nice: He has no problem pulling dirty tricks (though still legal) to bring the gang down.
- Hero Antagonist: He's an FBI agent tasked with taking the gang down.
- Inspector Javert: He's really determined to take down Doug's gang.
- Shotguns Are Just Better: He's primarily seen toting a shotgun as his main weapon.
A Boston Police Department detective tasked as Frawley's assistant.
The manager of a bank the gang robs, who ends up getting pulled into Doug's life.
- Break the Cutie: She winds up traumatized by the events at the start of the film, and then getting dragged into the investigation that follows.
- Stockholm Syndrome: She ends up starting a relationship with Doug, not realizing until later that he was the one who took her hostage.
- What the Hell, Hero?: Calls out Doug after Frawley tells her Doug's not only a bank robber, but the one who kidnapped her and gave her PTSD.