Though Boston gets most of the limelight when it comes to mafia dealings, one place outside the city has its own sordid past. The Winter Hill Gang operated out of Somerville in the 1960s and 1970s. Also known as the Winter Hill Mafia, it was one of Massachusetts’ most notorious organized crime groups.

The Winter Hill Gang was considered the top Irish Mob syndicate on the East Coast. Many considered them to be more threatening than the Boston faction of the mafia.
Flickr/Tim Sackton
The Winter Hill Gang takes its name from the Winter Hill neighborhood of Somerville. The group was founded by James "Buddy" McLean in 1950, but was most powerful between 1965 and 1979. A Boston Herald journalist in the 1970s dubbed them the Winter Hill Mafia, though the group was actually rivals with the famed Italian-America Patriarca crime family.
Along with fixing horse races and shipping weapons to the IRA, the group was responsible for crimes that ranges from loan sharking and illegal gambling to truck hijacking and contract killing.
Wikimedia Commons/FBI
The gang included notorious gangsters such as Whitey Bulger, Joe McDonald, Johnny Martorano, Howie Winter and Stephen Flemmi.

At least 21 members of the gang have been indicted in federal cases, including Howie Winter. After many of the original founding members of the gang were sent to prison in the 1970s, James "Whitey" Bulger and Stephen Flemmi remained as the leaders of the gang until 1991.

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Whitey Bulger fled Boston in 1994 due to an impending federal indictment.
Flickr/Tim Sackton
With a $2 million bounty on his head, he was finally captured in Santa Monica, California in 2011. Interestingly, he is the brother of William M. Bulger, former President of the Massachusetts Senate.

In 2013, Bulger was sentenced to two life terms in prison, plus five years. He was found guilty on 31 criminal charges including 19 murders, weapons charges, money laundering, extortion and racketeering.
Today, Somerville is a vibrant community of students, young professionals and families.
Flickr/Steven Isaacson

Today, Somerville is a vibrant community of students, young professionals and families. It’s hard to believe that the up-and-coming city was once the central node of a national crime group, but the Winter Hill Gang’s legacy has yet to fade from the memory of longtime Somerville locals.

For more hidden Massachusetts history, check out this list of horrifying Bay State stories you didn’t learn in history class.

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