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The Winter Hill Gang is a structured confederation of Boston, Massachusetts-area organized crime figures, predominantly Irish-American and Italian-American. It derives its name from the Winter Hill neighborhood of Somerville, Massachusetts north of Boston. Its members have included notorious Boston gangsters Howie Winter, James "Buddy" McLean, James J. "Whitey" Bulger, and John Martorano and Stephen "The Rifleman" Flemmi. They were most influential from 1965 under the rule of McLean and Winter until the takeover led by Bulger in 1979. The Winter Hill Gang was given its name in the 1970s by journalists at The Boston Herald, although the name was hardly ever openly used as a reference to them. While Winter Hill Gang members are alleged to have been involved with most typical organized-crime-related activities, they are perhaps most known for fixing horse races in the northeastern United States. Twenty-one members and associates, including Winter, were indicted by federal prosecutors in 1979.

They were heavily involved in illegal activities including racketeering, armed robbery, horse-race fixing, illegal gambling, drug trafficking, murder, extortion, prostitution, weapons trafficking, loan-sharking, hijacking and, corruption. Their allies are the Mullen Gang and their rivals were the Charlestown Mob and the Patriarca Crime Family.

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