Year: 2010 • Genre: Crime thriller, drama • Director: Ben Affleck • Cast: Ben Affleck, Rebecca Hall, Jeremy Renner, Jon Hamm, Blake Lively, Pete Postlethwaite • Setting: Charlestown and Boston, USA • Focus: Robbery crew, love, loyalty, and the cost of escape.
Plot and main characters
Doug MacRay (Ben Affleck) leads a small crew of bank robbers in Charlestown, Boston. His best friend, James “Jem” Coughlin (Jeremy Renner), is a fearless, hot-headed partner. During an early heist, the team takes a hostage—bank manager Claire Keesey (Rebecca Hall)—and later releases her unharmed. Worried she can identify them, Doug watches her, meets her “by chance,” and unexpectedly falls for her. Claire doesn’t know he was one of the robbers.
Meanwhile, FBI agent Adam Frawley (Jon Hamm) closes in. The crew keeps working: an armored truck job, close calls, and growing pressure. Charlestown’s crime boss, florist Fergie Colm (Pete Postlethwaite), controls the crew and pushes them into one huge final score: a robbery at Fenway Park. Doug wants out and dreams of leaving Boston with Claire, but Jem, Fergie, and Doug’s past pull him back.
- Doug MacRay — skilled planner who quietly wants a normal life.
- Jem Coughlin — loyal to Doug, but violent and impulsive.
- Claire Keesey — kind, smart bank manager trying to move on after the trauma.
- Agent Frawley — relentless FBI hunter who sees through lies.
- Krista Coughlin (Blake Lively) — Jem’s sister, Doug’s struggling ex, caught between love and survival.
- Fergie Colm — the local mobster who “owns” the town’s thieves and keeps them trapped.
Meaning
The film asks a simple question: can you escape the place that made you? Charlestown shapes Doug—crime is like a family business—but he still has a choice. Love with Claire gives him a glimpse of another life: honesty, sunlight, quiet. Loyalty to Jem and fear of Fergie pull the other way. The movie says environment is powerful, but it is not destiny. Every choice has a price. Doug’s path shows that redemption is real, but it rarely comes with a happy, easy ending. You may save someone else and still lose something of yourself.
Ending explained
The climax is the Fenway Park heist, the movie’s point of no return. The Fenway job forces everyone to show who they really are: Doug the planner, Jem the fighter, Frawley the hunter, and Claire the moral center.
- Fergie orders the job and threatens Claire, pushing Doug to comply.
- The crew robs the cash room at Fenway, dressed as cops. The police surround the stadium.
- During the escape, the crew is torn apart. Several are killed. Jem refuses to surrender and dies in a hail of bullets—his last act is defiance, not change.
- Doug slips away in disguise. He decides to end the cycle: he hunts down Fergie and kills him, cutting the strings that keep Charlestown tied to crime.
After that, Doug calls Claire. The FBI is with her and wants to trap him. But Claire warns Doug using a quiet code phrase they shared earlier: her “sunny days” line tells Doug not to come. He escapes the dragnet. This moment matters: Claire chooses compassion but not crime. She won’t turn him in, yet she won’t run away with him either.
Doug leaves a bag of money hidden in Claire’s community garden with a note. It’s not a romantic “let’s disappear” message. It’s a “make something good from this bad money” message. Later, we see the cash turned into something positive for Charlestown—often read as a community center or rink—something Claire can build without Doug. Then Doug disappears to a small house by the water in Florida 🌴, alive but alone.
| Character | Final state | What it means |
|---|---|---|
| Doug | Escapes, kills Fergie, lives in exile | He breaks the cycle but pays with isolation; redemption without reunion. |
| Jem | Killed in shootout at Fenway 🏟️ | Pure loyalty and rage lead to a dead end; he never wanted another life. |
| Claire | Uses the money for good, stays in Boston | She chooses healing over escape; love without crime, hope without Doug. |
| Agent Frawley | Misses Doug but cleans house | Law pushes crime back; not perfect justice, but pressure works. |
| Fergie | Killed by Doug | The old guard falls; the “town” loses its cruel gatekeeper. |
So what does the ending say? It’s not a fairy tale. Doug’s love for Claire is real, but his crimes are real too. He cannot give Claire a safe life if he stays with her. By walking away, he gives her freedom from his world. By leaving the money, he tries to repay the damage. And by killing Fergie, he cuts the root of the violence that trapped him and Jem. The final image—Doug alone by the water—tells us he saved others but could not save his own happiness 🧠. He chose to be better, and the cost was loneliness. That is the film’s hard truth: redemption can happen, but it rarely feels like victory.