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.
- Category Traitor: Doug views him as this, as they grew up in the same area, but he works for the police putting away criminals, including Doug's father.
- Mr. Exposition: Primarily exists to explain robbery tactics, or gather information on the gang.
- Southies: He grew up in Charlestown.
- The Stool Pigeon: His quick rise through the ranks was partly thanks to him tipping off the police to things he knew about Charlestown's criminals from growing up in the neighborhood.
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.