Winsor graduated in 1938 from the University of California, Berkeley. During her school years, she married a fellow student, All-American college football player Robert Herwig. In 1937, she began writing a thrice-weekly sports column for the Oakland Tribune. Although that job only lasted a year, Winsor remained at the newspaper, working as a receptionist. She was fired in 1938 when the newspaper chose to trim its workforce.
