In the 1960s, feuds between the Winter Hill Gang and their underworld rivals left dozens of mobsters dead across the Boston area — and that was just the beginning of the Irish mob’s bloody reign.
In the early 1960s, a group of Irish mobsters rose to prominence in the Boston area. They were known as the Winter Hill Gang — and they were ruthless.
Headed by Howie Winter and Buddy McLean, the group slowly eliminated all of its rivals through a series of Irish gang wars until it dominated Boston’s criminal underworld. From drug trafficking and fixing horse races to extortion and murder, the organization had a hand in a wide variety of illicit activities. It also allied with the Mafia — and this would lead to its downfall.
In the mid-1970s, gang member Whitey Bulger began working as an FBI informant, passing on intelligence about the mob’s Mafia allies in exchange for the agency’s protection. In 1979, the FBI arrested 21 mobsters, leaving leadership of the Winter Hill Gang up for grabs. Bulger swooped in to take control, but he made plenty of enemies in the process…