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Blinded by his past, Connolly grows closer to Whitey and the gang and even invites them to his house for a cookout. The FBI arrests the Angiulos, thus eliminating the remaining opposition to Whitey's power. When Connolly demands information on the Angiulos' racketeering locations, Whitey gets pictures of the rival gang's hideouts, allowing the FBI to plant wiretaps.
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Whitey increasingly exploits his status as an informant, using Connolly's "protection" as a cover for his crimes. Douglas suffers from Reye syndrome, leading the devastated Lindsey to remove him from life support over Whitey's furious objections.Īlthough Connolly is supported by his co-worker John Morris, their boss, Charles McGuire, is suspicious. Although Whitey hates the idea of being a rat, he understands the protection doing so would afford him, his gang, and his family. Connolly believes he can infiltrate the Angiulo Brothers' organization with Whitey's help. FBI agent John Connolly returns to the area, having grown up in South Boston as a friend of Whitey and his brother, Massachusetts Senate President William "Billy" Bulger.Īfter the Angiulo Brothers send a motorcycle-riding assassin who murders a Winter Hill soldier, Whitey becomes an informant for Connolly. Bulger lives with his longtime partner Lindsey Cyr and their young son Douglas.īulger's supremacy is challenged by the North End-based Angiulo Brothers, a rival gang that is part of the New England Mafia family. 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.