Winter was born in Boston on St. Patricks Day 1929 to a German father and an Irish mother in the Somerville section of Massachusetts. Winter became one of the original members of the Winter Hill Gang and was the protégé of the Gang's first boss James "Buddy" McLean. Other originating gang members, along with Winter and McLean, were Salvatore Sperlinga, Americo Sacramone, Anthony "Tony Blue" D'Agostino, Thomas Ballou Jr., "Joe Mac" Joseph McDonald, Russel Nicholson, and James "Spike" O'Toole.