Charles Comiskey was born in Chicago on August 15, 1859. He attended public and parochial schools in Chicago. He attended Saint Mary’s College where he played in the baseball team.
He played on many Chicago area baseball teams. He first was a pitcher but later moved to the first base position.
He worked as a player and a manager with Saint Louis Brown Stockings, the Chicago Pirates and the Cincinnati Reds.
He left Cincinnati in 1894 to purchase the Western League Baseball Club in Sioux City, Iowa. He moved the club to Minneapolis.