Winter Hill Gang

The Winter Hill Gang was a loose confederation of American organized crime figures in the Boston, Massachusetts, area. The organization itself derives its name from the Winter Hill neighborhood of Somerville, Massachusetts, north of Boston. The Winter Hill Gang was given its name in the 1970s by journalists at the Boston Herald. The gang formed in Somerville under the leadership of Howard "Howie" Winter and James "Buddy" McLean. It was generally considered an Irish mob organization, with most gang members and the leadership consisting predominantly of Irish-Americans, although some notable members, such as Stephen Flemmi and Johnny Martorano, were of Italian-American descent.

After vanquishing the McLaughlin Gang of Charlestown, then absorbing the remnants of the Mullen and Killeen gangs of South Boston following a series of Irish gang wars, the Winter Hill Gang was most influential from 1965, under the rule of McLean and Winter, to the 1979 takeover led by James "Whitey" Bulger. Twenty-one members and associates were indicted by federal prosecutors in 1979. Subsequently, Bulger and Flemmi seized control of the gang, relocating its headquarters to South Boston. Several other infamous Boston gangsters, such as Joseph "Joe Mac" McDonald, Patrick "Pat" Nee, Vincent "Jimmy the Bear" Flemmi, and Kevin Weeks, were among its members.

The Winter Hill Gang was the second most powerful criminal organization in New England, behind only the Patriarca crime family of Providence, Rhode Island. The gang was involved with most typical organized crime-related activities, including drug trafficking, gambling, and loan sharking, as well as fixing horse races throughout the northeastern United States, and shipping weapons to the Provisional Irish Republican Army (IRA).