The film begins in 1976 in South Boston during the Boston busing riots featuring a montage of documentary footage with voice-over narration by Irish mob boss Francis "Frank" Costello (Jack Nicholson). The next scenes take place sometime in the late 1980s with Frank Costello taking young Colin Sullivan under his wing, preparing him to be a mole for his crew. Years later, Sullivan (Matt Damon) is training for the Massachusetts State Police with classmates, including Agent Barrigan (James Badge Dale). In another class are Trooper Brown (Anthony Anderson) and William Costigan (Leonardo Dicaprio). Meanwhile, the cool and collected Captain Oliver Queenan (Martin Sheen) and the aggressive and foul mouthed Staff Sergeant Sean Dignam (Mark Wahlberg) of the Undercover Division assign Costigan, whose family has long had ties with the Boston underworld, to infiltrate Costello's crew.
In the present day, Sullivan is soon promoted to the Special Investigation Unit (S.I.U.) headed by the humorous Captain George Ellerby (Alec Baldwin). Costigan, having recently instigated a fight in a bar owned by Costello as well as beaten up two Italian mobsters from Providence in a separate incident, eventually gains the notice of Costello and becomes a member of his crew, pairing up with his second-in-command Mr. French (Ray Winstone) on a number of ordeals. Meanwhile, Sullivan begins a romantic relationship with criminal psychiatrist Madolyn Madden (Vera Farmiga), who is also having sessions with Costigan as a part of his probation for assault. Unknown to Sullivan, Costigan begins a relationship with Madolyn.
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 S.I.U., that being 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 S.I.U. to trail Queenan and eventually follows him to a meeting with Costigan on the rooftop of a run-down building on the harbor. 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 is defenestrated. A gun battle quickly ensues between Costello's men and the police officers who followed Queenan. In the ensuing gunfire, the police 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, Delahunt just before dying reveals to Costigan that he knows he's the mole, given that he was the one who called Costigan on the cell phone and gave him the wrong address to where Queenan was killed, yet he was still at the right address.
At the police precinct, a fist fight breaks out between Dignam and Sullivan over the circumstances of Queenan's death. 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. Still trying to locate the police mole in Costello's crew, 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.
A few nights later, Costello and his crew are being tailed to an old warehouse where they are to pick up a shipment of drugs. Sullivan disengages the tail at Costello's demand, and, fearing that he may be given away to the F.B.I. as well, 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, all of whom a wounded Costello abandons and escapes to another part of the warehouse, only to be confronted by Sullivan. Costello confirms that he is an informant and fires his gun at Sullivan, to which Sullivan returns multiple shots, killing him.
Later at the station, Sullivan arrives to praises from his coworkers, 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. The next morning, Madolyn is at Sullivan's apartment, 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. They arrange to meet.
On the rooftop where Queenan was killed, a hysterical Costigan confronts and handcuffs Sullivan. 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, dropping dead to the floor. Trooper Brown arrives and is killed by Barrigan as well. Barrigan reveals to Sullivan that he is the second mole in the police force and, being that they are the only ones remaining, need to look out for one another. As the two begin to manipulate the crime scene, Sullivan shoots Barrigan in the head. Sullivan later blames everything on Barrigan and recommends Costigan for a posthumous Medal of Merit.
Sullivan, along with many generations of the Massachusetts State Police force, attends Costigan's funeral, where a tearful Madolyn shuns him. Some time later, Sullivan returns home to find Dignam waiting in his apartment. Dignam shoots Sullivan in the head and quickly leaves. As Sullivan's body 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.
Famous Quotations : Frank Costello: When you decide to be something, you can be it. That's what they don't tell you in the church. When I was your age they would say we can become cops, or criminals. Today, what I'm saying to you is this: when you're facing a loaded gun, what's the difference?source :
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