Howard Thomas "Howie" Winter (born March 17, 1929) is an American mobster. He was the second leader of the infamous Winter Hill Gang.
Winter was born in 1929 of Irish and German ancestry, in West Roxbury, Massachusetts, but raised in nearby Somerville.
Winter was the right-hand man to the originator of the gang Buddy McLean and took over the rackets when Buddy 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 leader of the gang. Bulger and 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.
Winter was released from prison in 1987. In 1993, he was caught dealing cocaine. When the FBI informed him that Whitey had been a snitch 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.
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