 Constance Crawley died in 1919, after which Sayre in 1922 married his second wife, Mary Ward Holton (1888–1966), who had performed on Broadway under the stage name of Mary Ward.Although he continued in Broadway productions during the 1920s and 1930s, sometimes sharing the stage with Mary Ward, Sayre also did Shakespeare plays at the Garden Theatre, starring opposite Sybil Thorndike, Sydney Greenstreet and others.He was also a charter member with Eva Le Gallienne's Civic Repertory Theatre.