Charles Comiskey began his professional career in the minor leagues at the age of 17-18 in 1877. Comiskey reached the major leagues in 1882 with the St. Louis Brown Stockings (later Browns, then Cardinals) of the American Association (A.A.), where he remained through 1891. His best season was probably 1887, when Comiskey batted .335 with 103 RBI, 139 Runs, 180 Hits, and 117 SB's in 538 AB's. He was a major contributor to the Brown's 4 straight pennants between 1885-1888, including a World Series Championship over the N.L. Chicago White Stockings (Cubs) in 1886. In 1892, Comiskey went to play for the N.L. Cincinnati Reds for 3 years through the 1894 season before finishing out his playing career in the minors in 1898
Comiskey began managing professionally as a player for the Browns in 1883, and remained a player-manager throughout the rest of his career. He managed for an additional two years after his playing career, ending with the A.L. Chicago White Stockings at the age of 40-41 in 1900.