Howard Thomas Winter
March 17, 1929
Winter was the right-hand man to the originator of the gang, James "Buddy" McLean and took over the rackets when McLean was killed during the Irish Mob Wars in 1966. In 1979 Winter and members of the Winter Hill Gang were arrested and indicted on federal "horse race fixing" charges. James "Whitey" Bulger then replaced Winter as boss of the gang.
Winter was released from prison in 1987 he relocated to St. Louis where he was in contact with gang associate James "Gentleman Jim" Mulvey and close friend of Raymond Patriarca. In 1993, he was caught dealing cocaine. When the FBI informed him that Bulger had been an informant all those years and offered Winter a deal if he would inform on Bulger, Winter refused the deal telling the FBI that Mulvey has already informed him of that and he was no "rat", despite facing another decade behind bars, which he would serve, being released from prison in July 2002.
Following his release from prison, Winter worked out of his home in Millbury as a property manager. In 2012, Winter was arrested on charges of extorting money from two people. He was released on bail and the trial is still pending.
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- Martini, Bobby and Keratsis, Elayne. "Citizen Somerville: Growing Up With The Winter Hill Gang." Boston, Massachusetts: Powderhouse Press, 2010. Template:ISBN 9780982991503
- Matera, Dary. FBI's Ten Most Wanted. New York: HarperCollins, 2003. ISBN 0-06-052435-9
- Willis, Clint (ed.) Wise Guys: Stories of Mobsters from Jersey to Vegas. New York: Thunder's Mouth Press, 2003. ISBN 1-56025-498-X
- English, T.J. Paddy Whacked: The Untold Story of the Irish American Gangster. New York: HarperCollins, 2005. ISBN 0-06-059002-5
- "Locate a Federal Inmate: Howard Winter". Federal Bureau of Prisons. 2011. Retrieved 2011-06-27.
- "Howie Winter, former head of Winter Hill Gang, to be arraigned in Somerville District Court". Boston.com. Retrieved 2015-12-30.