Former Winter Hill Gang Leader Howie Winter Dies At 91

Somerville MA

14 November, 2020

2:16 PM

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SOMERVILLE, MA — Longtime Winter Hill gang leader Howie Winter died Thursday. He was 91 and had been living in Millbury. Winter was a looming figure in the Boston underworld in the 1960s and 70s as the leader of the notorious Irish gang. Winter served time in prison for race-fixing and drug trafficking, during which James "Whitey" Bulger emerged as the gang's leader. In his later years, Winter tried to help the Isabella Stewart Gardner Museum recover $500 million worth of artwork stolen in an infamous 1990 heist, telling The Boston Globe in 2018 he was "an art lover myself." Thomas Foley, a retired Massachusetts State Police colonel who investigated organized crime, told The Globe Winter was a "guy that actually got away with murder." Winter's cause of death was a heart attack, The Globe reported. "Howie loved his wife, politics, his service in the Marine Corps, and a good argument," his obituary states. A wake will be held Monday in Somerville, followed by a funeral mass and procession Tuesday.