Howard Thomas Winter (March 17, 1929 – November 12, 2020) was an American mobster who was a boss of the Winter Hill Gang in Somerville, Massachusetts.

Early life

Winter was born in Boston, Massachusetts on March 17, 1929. He was of German and Irish descent.

Irish Mob

Winter was the right-hand man to the originator of the gang, James "Buddy" McLean and took over the rackets, along with Joe McDonald, when McLean was killed during the Irish Mob Wars in 1965. In 1979 Winter, McDonald and other 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 and relocated to St. Louis, where he was in contact with gang associate James "Gentleman Jim" Mulvey, who was a close friend of Raymond L. S. 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.

Later life and death

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 pled guilty and was placed on probation. Winter died in 2020, aged 91.