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 later returned to the newspaper to work as a receptionist. She was fired in 1938 when the newspaper chose to trim their workforce. Winsor became interested in the Restoration period through her husband. Herwig was writing a paper for school on Charles II, and, out of boredom, Winsor read one of his research books. Winsor found it unthinkable to return to the married life she had known with Herwig and, in 1946, they divorced