Fact1: James Whitey Bulger controls most organized crime within South Boston along with right-hand man Stephen Flemmi and callous hitman Johnny Martorano, Fact2: Bulger 's supremacy is challenged by North End Angiulo Brothers, Fact3: Connolly grew up in South Boston as friend of Whitey and brother William Billy Bulger, Fact4: Whitey understands protection for himself gang and family, Fact5: Douglas suffers from Reye syndrome leading devastated Lindsey to remove him from life support over Whitey 's furious objections
Output: In 1975, James Whitey Bulger, leader of the Winter Hill Gang, controls most organized crime within South Boston, along with his righthand man Stephen Flemmi, newcomer Kevin Weeks, and callous hitman Johnny Martorano. Bulger lives with his commonlaw wife Lindsey Cyr and their young son Douglas. Bulgers 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 Whiteys furious objections. When the Angiulo Brothers murder a Winter Hill member, Whitey becomes an informant. Although Connolly is supported by his coworker John Morris, their boss, Charles McGuire, is suspicious. Whitey increasingly exploits the FBI informant relationship, using Connollys protection as a cover for his crimes. Connolly demands information on the Angiulos racketeering locations. Finally, Whitey gets pictures of the rival gangs hideouts, allowing the FBI to wiretap the Angiulos. The FBI arrests them, thus eliminating underground opposition to Whiteys 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 agentinformant 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 Whiteys involvement, much to Connollys displeasure, who then tells Whitey of Hallorans accusation, thereby resulting in the murders of Halloran and an unnamed accomplice. Following the passing of his mother, Whiteys behavior becomes increasingly violent and unpredictable, deteriorating his informant relationship. A bulldog prosecutor, Fred Wyshak, is appointed the new 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 Connollys management of Whiteys informant role. They discover that most of what Connolly called Whiteys tips were already obtained from other sources. Morris, disillusioned and fearing prosecution for his association with Connollys activities, anonymously divulges Connollys and Whiteys relationship to the Boston Globe and a frontpage story exposes the FBIs 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 states evidence and testifies against Connolly in return for immunity. Connollys and the other characters sentences are listed, and a concluding sequence shows a nowelderly Whitey being caught by the FBI in 2011.