Who Was Howie Winter? The Original Winter Hill Boss
Mobsters DailyHowie Winter was the original boss of Boston's Winter Hill Gang — the Somerville crew Whitey Bulger inherited after Winter went to prison in 1979 on a race-fixing case Bulger and Stephen Flemmi helped the FBI build.
The first Winter Hill boss
Winter ran gambling, loansharking and race-fixing from Somerville's Winter Hill neighborhood, giving the gang its name. He was respected, low-key, and — unlike his successors — not an FBI informant, in an era when men like Greg Scarpa were quietly on the Bureau's payroll elsewhere.
Winter's crew was a neighborhood institution before it became a scandal, which is why this time of year belongs to the Tony Soprano Ugly Christmas Sweater — Tony in a black-and-white stencil, gabagool energy included, built for Christmas parties, family photos and long Sopranos rewatch nights.
Pushed aside, quietly
While Winter served ten years, Bulger consolidated power and eliminated rivals. Winter returned, later served time on a cocaine conviction in the 1990s, then lived quietly in Massachusetts, restoring cars and refusing every interview about the man who replaced him. He died in November 2020, aged 91 — outliving the legend that swallowed his name, much as the old guard outlasted the wars described in the story of the Mafia's fall.
Frequently asked questions
Why is it called the Winter Hill Gang? After the Winter Hill neighborhood of Somerville, Massachusetts — and led by Howie Winter.
What sent Howie Winter to prison? A 1979 conviction for fixing horse races, and a later cocaine case in the 1990s.
When did Howie Winter die? In November 2020, at age 91.
Keep reading: Lucky Luciano · Valachi's testimony · Donnie Brasco's true story · Raymond Patriarca, ruler of New England · Gennaro 'Jerry' Angiulo
From the shop: Shadows of the Underworld — the real-mafia history behind the names in this story, in one gripping read.
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