Howie Winter

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Howie Winter
Howie Winter - Undated mug shot
Born Howard Thomas Winter
(1929-03-17) March 17, 1929 (age 87)
West Roxbury, Massachusetts, U.S.
Occupation Mobster

Howard Thomas "Howie" Winter (born March 17, 1929) is an American mobster. He was the second boss of the infamous Winter Hill Gang.

Early life[edit]

Winter was born in 1929 of Irish and German ancestry, in West Roxbury, Massachusetts, but raised in nearby Somerville.

Irish Mob[edit]

Winter was the right-hand man to the originator of the gang 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. Bulger and Stephen "The Rifleman" Flemmi were on the original indictment, but FBI agents John Morris and the later disgraced John Connolly convinced federal prosecutor Jeremiah O'Sullivan to remove Bulger and Flemmi from the indictment because they were informants.[citation needed]

Winter was released from prison in 1987. 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 he was no "rat", despite facing another decade behind bars, which he would serve, being released from prison in July 2002.[1]

Later life[edit]

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.[2]

Further reading[edit]

  • Bloom, Robert M. Ratting: The Use and Abuse of Informants in the American Justice System. Westport, Connecticut: Greenwood Publishing Group, 2002. ISBN 0-275-96818-9
  • 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
  1. ^ "Locate a Federal Inmate: Howard Winter". Federal Bureau of Prisons. 2011. Retrieved 2011-06-27. 
  2. ^ "Howie Winter, former head of Winter Hill Gang, to be arraigned in Somerville District Court". Retrieved 2015-12-30. 

External links[edit]