Born in Chicago, Illinois into a family of 16 children, O'Leary worked at age 16 for a clothing company and played on the company's semi-pro baseball team. His talent as a middle infielder and scrappy hitter came to the attention of Charles Comiskey, owner of the Chicago White Sox. Though there is no independent verification, O'Leary reportedly signed briefly with the White Sox, only to have his arm broken from a pitched ball thrown by 'fireballer' and Hall of Famer, Rube Waddell.
Major Leagues
O'Leary major league debut was on April 14, 1904 with the Tigers. He was Detroit's starting shortstop from 1904–1907 and became a backup shortstop and utility infielder from 1908–1912. In the off-season, O'Leary and teammate Germany Schaefer, known as one of baseball's zaniest characters, worked as a comic vaudeville act. The O'Leary-Schaefer vaudeville act is said to have inspired two Metro-Goldwyn-Mayer musicals: the forgotten 1930 filmThey Learned About Women, featuring the noted vaudeville act Van and Schenck, and Busby Berkeley's last film, Take Me Out to the Ballgame, with Gene Kelly and Frank Sinatra. Not known for his hitting, O'Leary had a career batting average of.226. After finishing his playing career in 1913 with the St. Louis Cardinals, O'Leary was a player-manager in the minor and semi-pro leagues for several years, including in San Francisco, St. Paul, San Antonio, and Chicago, until he was offered a coaching job in 1920 by his close friend, Miller Huggins, manager of the New York Yankees. 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 coached for the Yankees for 10 years, during which they won six pennants and two World Series, including the great 1927 Yankees team. O'Leary then coached with the Chicago Cubs under Rogers Hornsby, and with the St. Louis Browns. On September 30, 1934, several weeks shy of his 59th birthday, O'Leary was called out of retirement by the Browns. In a pinch-hitting appearance, he singled and scored, becoming both the oldest Major LeagueBaseball player to collect a hit and to score a run.
