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The Departed
In 1980s Boston, Irish mob boss Frank Costello introduces himself to a young Colin Sullivan. Years later, Sullivan has been groomed as Costello's spy inside the Massachusetts State Police (MSP) and joins the Special Investigation Unit. Another police academy recruit, Billy Costigan, is selected by Captain Queenan and Sergeant Dignam to infiltrate Costello's organization.
Serving a prison term as his cover, Costigan draws Costello's attention by committing several crimes, and is recruited into the gang. His mental state declines as he becomes increasingly involved in Costello's violent criminal enterprise, but Queenan and Dignam convince him to remain undercover. Sullivan begins dating police psychiatrist Madolyn Madden, who becomes Costigan's court-ordered therapist.
Costigan notifies the MSP that Costello will be selling stolen microprocessors to Chinese mobsters, but Sullivan helps thwart the attempted sting operation. Costello and the MSP both realize they have been compromised, and both Costigan and Sullivan are tasked to find the opposing mole. Costigan learns Costello is a protected FBI informant, sharing his discovery with Queenan. He and Madden begin an affair.
Following Costello, Costigan sees him give Sullivan an envelope of information on his crew. Costigan is unable to identify Sullivan, who realizes he is being followed and mistakenly stabs a passerby before fleeing. Lying to his fellow officers to have Queenan followed, Sullivan realizes Queenan is meeting with his mole, and informs Costello's gang.
Costigan, fearing he will be discovered and killed for being the mole, meets with Queenan to abort the operation. However, Queenan helps Costigan escape as Costello's men arrive, and is thrown from the building to his death. Fatally wounded in the ensuing firefight with police, Costello's henchman Timothy Delahunt tells Costigan he knows that he is the mole before dying.
In the wake of Queenan's murder, Dignam is suspended after an altercation with Sullivan, who learns from Queenan's files that Costello is cooperating with the FBI. A news report identifies Delahunt as a Boston Police Department undercover officer, but Costello suspects this is a ruse to protect the real mole. Sullivan directs the MSP to tail Costello, resulting in a gunfight that kills most of Costello's crew. Sullivan confronts a wounded Costello, who admits to being an informant. They exchange gunfire, and Sullivan kills him.
His assignment finished, Costigan reveals himself to Sullivan but recognizes Costello's envelope on his desk, deducing Sullivan is Costello's mole. Costigan flees, and Sullivan realizes he has discovered the truth, deleting Costigan's police records. Costigan leaves an envelope of evidence with Madden, who finds a recording he mailed to Sullivan of Sullivan's incriminating conversations with Costello.
Meeting Sullivan on the rooftop where Queenan was killed, Costigan arrests him. Trooper Brown, Costigan's police academy classmate, arrives as Costigan holds Sullivan at gunpoint, declaring he has evidence tying Sullivan to Costello. Taking the elevator to the lobby, Costigan is shot and killed by Trooper Barrigan, who reveals he is another of Costello's spies in the MSP. Brown is shot by Barrigan, who, in turn, is shot by Sullivan, framing Barrigan as Costello's only mole.
Sullivan recommends Costigan be posthumously commended, but after Costigan's funeral, a pregnant Madden leaves him. He arrives home to find Dignam, who shoots him and departs.