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The Winter Hill Gang was a loose confederation of American organized crime figures in the Boston, Massachusetts area. 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, are of Italian-American descent.
James Joseph "Whitey" Bulger Jr. (/ ˈ b ʌ l dʒ ər / ⓘ; September 3, 1929 – October 30, 2018) was an American organized crime boss who led the Winter Hill Gang, an Irish Mob group based in the Winter Hill neighborhood of Somerville, Massachusetts, northwest of Boston.
John "Red" Shea (born August 12, 1965) is an American former mobster from Boston involved in narcotics and an associate of crime kingpin Whitey Bulger and the Winter Hill Gang during the 1980s and 1990s. He was indicted on cocaine trafficking charges in 1990 and served 12 years in prison.
Timothy A. Connolly III (May 27, 1958 - July 21, 2020), aka "Timmy Connolly" and "TC", was an American former South Boston bar owner and mortgage broker, who wore a wire inside the infamous Winter Hill Gang and helped the federal government indict their two leaders, James "Whitey" Bulger and Stephen Flemmi ("The Rifleman").
Kevin Weeks (born March 21, 1956) is an American former mobster and longtime friend and mob lieutenant to Whitey Bulger, the infamous boss of the Winter Hill Gang, a crime family based in the Winter Hill neighborhood of Somerville, Massachusetts. After his arrest and imprisonment in 1999, he became a cooperating witness.
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Martorano rapidly became one of the Winter Hill Gang's most prolific enforcers under the tenures of Howie Winter and Whitey Bulger. In January 1968, after Hubert "Smitty" Smith, an African-American man, helped mobsters Rocco Lammattina and John Cincotti beat up Flemmi in an after-hours saloon, Martorano confronted Smith at the saloon the night ...
Younger brother of Johnny Martorano; Winter Hill Gang associate and member of the Patriarca crime family: Johnny Martorano 1: No image available: 1940– 1964–1995 Hitman for the Winter Hill Gang and older brother of James Martorano Joseph McDonald: No image available: 1917–1997 One of the charter members of the Winter Hill Gang: Michael ...