Born in Chicago, Illinois into a family of 16 children (11 boys), O\'Leary worked at age 16 for a clothing company and played on the company\'s semi-pro baseball team.[citation needed] 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.\n', '

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.\n', '

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 film They Learned About Women, featuring the noted vaudeville act Van and Schenck, and Busby Berkeley\'s last film, Take Me Out to the Ballgame (1949), with Gene Kelly and Frank Sinatra.[citation needed]\n', '

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