O'Leary made his major league debut on April 14, 1904, with the Tigers. He was Detroit's starting shortstop from 1904 to 1907 and became a backup shortstop and utility infielder from 1908–1912. The O'Leary-Schaefer vaudeville act is said to have inspired two
Metro-Goldwyn-Mayer musicals: the forgotten 1930 film
They Learned About Women and
Busby Berkeley's last film,
Take Me Out to the Ballgame (1949), with
Gene Kelly and
Frank Sinatra. After a 17–0 victory over the
Washington Senators on July 6, 1920, O'Leary was returning to New York in a car driven by
Babe Ruth, along with Ruth's wife Helen, rookie outfielder
Frank Gleich, and second-string catcher
Fred Hofmann. Ruth lost control of the car, and O'Leary was ejected from the vehicle, although he suffered only minor injuries. He then coached with the Yankees for 10 years, during which period they won six pennants and two
World Series, including the great
1927 Yankees team. ==Date of birth==