Winter Hill Gang

About Winter Hill Gang

The Winter Hill Gang is a loose confederation of Boston, Massachusetts-area organized crime figures, predominately Irish-American with a small Italian-American faction. 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 McLean ("Buddy"), James J. Bulger ("Whitey"), and hitman Stephen Flemmi ("The Rifleman"). They were most influential from 1965 under the rule of James "Buddy" McLean and Howard "Howie" Winters until the takeover led by James J. Bulger in 1979. The Winter Hill Gang did not receive its title until the 1970s from 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 north-eastern United States. Twenty-one members and associates, including Bulger's predecessor Howie Winter, were indicted by federal prosecutors in 1979.

The Boston Irish Gang War started in 1961 and lasted until 1966. It was fought between the McLaughlin Gang of Charlestown, led by Bernie McLaughlin and the Winter Hill Gang of Somerville, led by James "Buddy" McLean.

The two gangs had co-existed in relative peace for a number of years until an incident on Labor Day weekend 1961. While at a party, Georgie McLaughlin made an advance on the girlfriend of Winter Hill Gang member Alex Rocco He was subsequently beaten unconscious by members of the Winter Hill Gang and was dumped outside of the local hospital.