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SYNOPSIS
In 1975, James "Whitey" Bulger, leader of the Winter Hill Gang, controls most organized crime within South Boston, along with his right-hand man Stephen Flemmi, newcomer Kevin Weeks, and callous hitman Johnny Martorano. Bulger lives with his common-law wife Lindsey Cyr and their young son Douglas.
Bulger's supremacy is challenged by the North End Angiulo Brothers, a rival gang that is part of the New England Mafia family. FBI agent John Connolly returns to the area – he grew up in South Boston as a friend of Whitey and his brother William "Billy" Bulger, the Massachusetts Senate President. Connolly tries infiltrating the Angiulo Brothers, and attempts to get Whitey to work with the FBI. Although Whitey hates the idea of being a rat, he understands the protection he would have for himself, his gang, and his family. Douglas suffers from Reye syndrome, leading a devastated Lindsey to remove him from life support over Whitey's furious objections. When the Angiulo Brothers murder a Winter Hill member, Whitey becomes an informant.
Although Connolly is supported by his co-worker John Morris, their boss, Charles McGuire, is suspicious. Whitey increasingly exploits the FBI informant relationship, using Connolly's "protection" as a cover for his crimes. Connolly demands information on the Angiulos' racketeering locations. Finally, Whitey gets pictures of the rival gang's hideouts, allowing the FBI to wiretap the Angiulos. The FBI arrests them, thus eliminating underground opposition to Whitey's power. Connolly, blinded by his past, grows closer to Whitey and the gang, even inviting them to his house for a cookout. His wife, Marianne, sees negative changes in her husband as his agent-informant relationship with Whitey grows.
Cut out of an embezzlement scheme from World Jai Alai, Whitey orders Martorano to murder his rivals Roger Wheeler and John Callahan. An associate, Brian Halloran, goes to the FBI to report Whitey's involvement, much to Connolly's displeasure, who then tells Whitey of Halloran's accusation, thereby resulting in the murders of Halloran and an unnamed accomplice. Due to Whitey's increasingly violent and unpredictable behavior, his informant relationship deteriorates.
A "bulldog" prosecutor, Fred Wyshak, becomes an assistant U. S. Attorney in Boston. Connolly attempts to make friends and to perhaps divert his attention from Bulger, but Wyshak bluntly refuses, demanding that the FBI arrest Whitey. John McIntyre, an informant within the Winter Hill Gang, informs on an attempt by Whitey to smuggle weapons for the IRA. Connolly tells Whitey, who murders McIntyre. Wyshak and McGuire investigate Connolly's management of Whitey's informant role. They discover that most of what Connolly called Whitey's tips were already obtained from other sources. Morris tells the Boston Globe about Connolly's and Whitey's relationship and a front-page story exposes the FBI's links to organised crime.
In the final scenes, Connolly, Flemmi, Weeks, and Martorano are arrested. Whitey goes on the run, but not before giving Billy a final goodbye from a pay phone. Morris turns state's evidence and testifies against Connolly in return for immunity. Connolly's and the other characters' sentences are listed, and a concluding sequence shows a now-elderly Whitey being caught by the FBI in 2011.
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