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The Winter Hill Gang was a loose confederation of organized crime figures in the Boston, Massachusetts, US, area.It was generally considered an Irish Mob organization, with most gang members and the leadership consisting predominantly of Irish-Americans, though 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.
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.
Bulger ruled over Boston’s infamous Winter Hill gang during the 1970s and ’80s, committing what a judge would later describe as “unfathomable” acts that terrorized the city.
Born in South Boston in 1929, Bulger ran the notorious Winter Hill Gang throughout the 1970s and 1980s, which became the top Irish mob organisation in the city after beating its rivals in a gang war.
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").
Patrick Joseph Nee (born December 22, 1944) is an Irish-American former mobster and Irish republican sympathizer. A former member of the Mullen Gang and the Winter Hill Gang, he is a Vietnam War veteran, and author of A Criminal and an Irishman; The Inside Story of the Boston Mob-IRA Connection.
Stephen Joseph Flemmi (born June 9, 1934) is an American gangster and convicted murderer and was a close associate of Winter Hill Gang boss Whitey Bulger.Beginning in 1975, Flemmi was a top echelon informant for the Federal Bureau of Investigation (FBI).