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.

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.

[1] 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.