About Charley O'Leary
Lived 1875 – 1941 (aged 65). Charley O'Leary was an American baseball player.
Charles Timothy O'Leary (October 15, 1875 – January 6, 1941) was an American professional baseball shortstop who played eleven seasons with the Detroit Tigers (1904–1912), St. Louis Cardinals, and St. Louis Browns (1934) of Major League Baseball (MLB).
Early life Born in Chicago, Illinois to Irish immigrants Timothy and Ellen O’Leary, who had 16 children (11 boys). O'Leary worked at age 16 for a clothing company and played on the company's semi-pro baseball team. In 1900, while working as a messenger boy, he was sent to the ballpark of the Chicago White Stockings; when their shortstop, Frank Shugart, was injured, O'Leary was recruited on the spot, based on the recommendation of someone who knew him. His talent as a middle infielder and scrappy hitter came to the attention of Charles Comiskey, owner of the White Stockings (later the Chicago White Sox). Though there is no independent verification, O'Leary reportedly signed briefly with the team, only to have his arm broken from a pitched ball thrown by 'fireballer' and Hall of Famer Rube Waddell. 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 During his career, O'Leary claimed to have been born in 1882. However, in 2010, a researcher for the Society for American Baseball Research found him in the 1880 census. His draft record for World War I, which showed that he was born in 1875, was subsequently located. This made him the second-oldest Major League Baseball player to appear in a game, after Satchel Paige.
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Important facts
People in Charley O'Leary's life
Named in this biography and alive at the same time
Contemporaries
People whose lives overlapped Charley O'Leary's
Frequently asked questions
Who was Charley O'Leary?
American baseball player and coach (1875–1941)
When was Charley O'Leary born?
Charley O'Leary was born on 15 October 1875 in Chicago.
When did Charley O'Leary die?
Charley O'Leary died on 6 January 1941 in Chicago.
What was Charley O'Leary's occupation?
Charley O'Leary was a baseball player.
What nationality was Charley O'Leary?
Charley O'Leary was American.
Sources & further reading
Cite this page
APA: Biography.guide. (2026). Charley O'Leary. https://biography.guide/charley-o-leary/
MLA: "Charley O'Leary." Biography.guide, https://biography.guide/charley-o-leary/.
Chicago: "Charley O'Leary." Biography.guide. https://biography.guide/charley-o-leary/.
Data last updated: 2026-09-20 · Spot an error? Report a correction.
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