The film begins in South Boston and Charlestown during the Boston riots featuring a montage of documentary footage with voice-over narration by Irish mob boss Francis "Frank" Costello (Jack Nicholson). In the early 1990s, Costello is in a local store to collect his pay-off money from the owner. A young boy is there, Colin Sullivan, who Frank takes a liking to. Using his influence, he has the owner give Colin two bags of groceries and tells him to come look for him, if he ever wants to "earn" some extra money.
CUT TO: Many years later, an older Sullivan, now in his mid twenties, (Matt Damon) is finishing his training for the Massachusetts State Police with classmates, including fellow cadet Barrigan (James Badge Dale). In another class are cadet Brown (Anthony Anderson) and Billy Costigan (Leonardo DiCaprio). All four men graduate to become state troopers. Sullivan is a sergeant, and has just passed the state trooper detective test. He goes in to meet with the calm and collected Captain Queenan (Martin Sheen), and the aggressive and cynical Staff Sergeant Dignam (Mark Wahlberg) of the Special Investigations Unit. When Sullivan exits, Costigan goes in. The undercover division of the Special Investigations Unit wants to assign Costigan, whose family has long had ties with the Boston underworld, to infiltrate Costello's crew. For his service, he gets a "bonus", tax-free payment upon completion of his assignment. To make his assignment believable to everyone, especially Costello, they create a false conviction on Costigan for assault. He will get a four month jail sentence and afterwards probation with mandatory sessions with a psychiatrist. His police academy record and file are concealed from the public, and even the department itself, and the only ones who can access Costigan's file are Queenan and Dignam.
Sullivan, along with Barrigan and Brown, is now in an elite task force of the Special Investigations Unit (SIU) headed by the sardonically humorous Captain Ellerby (Alec Baldwin). They are after Costello and are coordinating with the FBI. Staff Sergeant Dignam introduces himself to the group but does not reveal whether or not they have a mole in Costello's gang. They briefly go over what it is that the department is targeting: Francis Costello and military micro-chips. They expect that Costello will sell them to China. A freelance thief had stolen the twenty micro-processors but somehow ended up deceased in a dumpster.
Costigan is out of jail and uses his drug-dealing cousin as a back-handed way of attracting Costello's attention and fights a man in a bar. He then becomes a member of his crew, pairing up with his right-hand man Mr. French (Ray Winstone). Costello tells Costigan that he knew, respected, and feared his father and Uncle Jackie, both of whom were heavily involved in the criminal underworld. It is therefore these two family connections which really motivate Costello more than anything else to try to assist Costigan in his own questionable way.
Meanwhile, Sullivan begins a romantic relationship with criminal psychiatrist Madolyn (Vera Farmiga), who also happens to be the assigned psychotherapist for Costigan as a part of his probation for the fabricated assault conviction. Although she wants to keep their relationship professional, a romance develops, but Costigan and Sullivan remain oblivious to each other's identity.
During one of his heists Costello, through Sullivan's information, discovers that there is a police informer in his organization. To catch the insider, he requires each member to fill in his particulars in a form, including social security numbers. Costigan knows that this envelope will end up in the hands of Costello's man at the police. He follows Costello (who has the envelope) into a pornography theater, where he witnesses Costello handing over the envelope to Sullivan, whose face is hidden in the darkened auditorium. Attempting to disclose the mole's identity, Costigan shadows Sullivan into the streets, only to eventually lose him in Boston's Chinatown neighborhood.
Meanwhile, Sullivan is assigned to uncover the mole in SIU (himself). This makes for some tension between Sullivan and Dignam, whose suspicion of Sullivan rises. Above suspicion, Sullivan focuses instead on finding the police snitch in Costello's crew. Sullivan orders the SIU to trail Queenan and eventually follows him to a meeting with Costigan on the rooftop of a run-down building on the harbor. Having become insomniac, dependent on Valium and suffering from panic attacks, Costigan explains he wants out, to which Queenan assures him that while it cannot be done overnight, he will get him out of it. Sullivan tells Costello's men that the snitch is most likely at the building. As the men approach, Costigan flees, but Queenan stays behind and is confronted by them and thrown off the building to his death. In the ensuing gunfire, between Costello's men and the police, the officer who tailed Queenan is wounded and Delahunt, one of Costello's men is critically wounded. Later on, when the men return to their hideout, Timothy Delahunt (reported later by the local media to be yet another undercover officer, possibly made public by the state police to throw suspicion off of Costigan) reveals to Costigan - just before he succumbs to his wounds - that he knows he's the mole.
Sullivan orders Dignam to hand over the information regarding his undercover, which Dignam refuses. Ellerby, who has taken over the department for Queenan, orders Dignam off duty with pay for two weeks. Guilt-ridden over having indirectly caused his senior officer's death, Sullivan finds Queenan's cell phone in his homicide file and calls Costigan, pretending to be the new agent assigned to replace Queenan. After Costigan hangs up, Sullivan finds information in Queenan's file indicating that Costello is an informant for the Federal Bureau of Investigation and immediately begins to fear betrayal.
Costello and his crew are being tailed to an old warehouse where they are to pick up a shipment of cocaine. Sullivan disengages the tail at Costello's demand and sets up a police ambush at the scene instead. Costigan, wary that the police potentially know of the situation, manages to slip away unnoticed. Costello's entire crew is killed in the ensuing shoot-out, and a wounded Costello abandons the car in which Arnold French and he were driving and escapes to another part of the warehouse, only to end up in a tense confrontation with Sullivan. Costello admits to his informant status and denies telling anybody about Sullivan's connection to him as he feels Sullivan is like a son to him but Sullivan doesn't believe Costello and insults him before Costello attempts to shoot him. After an exchange of gunshots Costello is killed by Sullivan.
Later at the station Sullivan arrives to praise from his co-workers and meets Costigan, who asks to simply receive his payment and be allowed to leave. While Sullivan retrieves Costigan's information in another office, Costigan notices Costello's envelope on Sullivan's desk and quickly flees. Sullivan realizes that Costigan has discovered his true identity and erases Costigan's police file. Following his flight from the station, Costigan appears outside of Madolyn's office. He gives her an envelope, telling her to open it if anything should happen to him, or if he calls and tells her to open it. On a subsequent morning, Madolyn is at the apartment she shares with Sullivan, and finds an envelope from Costigan in his mail. It contains recordings of Sullivan and Costello's conversations, along with a phone number. Madolyn reveals the recordings to Sullivan and immediately ends her relationship with him. Sullivan calls the phone number and speaks to Costigan, who reveals to Sullivan that Costello kept the recordings as insurance to use as a possible legal immunity if he was arrested. He also reports to Sullivan that Costello's lawyer came to Bill with the recordings, meaning that Costello trusted Costigan the most of all of his men. They arrange to meet where Queenan died.
On the rooftop where Queenan was killed, Costigan confronts and handcuffs Sullivan, intending to arrest him regardless if the charges don't stick. Trooper Brown appears and tries to talk down Costigan, who, claiming that he has substantial proof that Sullivan is the rat, quickly flees into an elevator, holding his gun to Sullivan's head. The elevator reaches the bottom floor, and just as Costigan begins to exit, he is shot in the head by Barrigan. Barrigan starts to uncuff Sullivan but then Trooper Brown arrives and sees Costigan's body and is caught off guard, allowing Barrigan to shoot him in the head and remove the only witness to Sullivan's guilt. Barrigan reveals to Sullivan that he is also a mole in the police force and aware of Costello's informant status. Being that they are the only ones remaining, Barrigan says they need to look out for one another. As the two begin to manipulate the crime scene, Sullivan asks for the gun to clean the fingerprints, and as Barrigan looks away, Sullivan shoots him in the head. To save himself, he blames everything on Barrigan and recommends Costigan for a posthumous Medal of Merit in a later testimony. At Costigan's funeral, Madolyn, now pregnant with either Sullivan or Costigan's child, walks away from Sullivan in silence.
Following the funeral, Sullivan returns home to find Dignam waiting there, having been tipped off by Madolyn about his connection to Costello. Dignam shoots him in the head and quickly leaves. As Sullivan's corpse lies in the apartment doorway, the camera pans out and a lone rat crawls conspicuously across the balcony railing, silhouetted against the gold dome of the Massachusetts State House.
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