Before he was nicknamed "The Old Roman," Charley Comiskey was just a kid who loved baseball. The third of eight children, Comiskey was discouraged from playing the game by his father, "Honest" John Comiskey, who was a politician in the Windy City’s Holy Family Parish. The young Comiskey persevered, however, and he made his professional debut with the St. Louis Brown Stockings of the American Association in 1882. Comiskey played eight seasons with St. Louis, mostly at first base, and by 1887, he had racked up 139 runs and 117 stolen bases, the third most steals in a season before the modern era (before 1900). From 1883 to 1889 he served as St. Louis’ player-manager, leading his team to the American Association pennant four consecutive seasons from 1885 to 1888. In 1890, he left St. Louis for the Chicago franchise of the short-lived Players League. Comiskey then ended his playing and managing career with the Cincinnati Reds of the National League, retiring after the 1894 season with a managerial record of 838-541. His .608 career winning percentage is the second best in baseball history behind Joe McCarthy.
Comiskey went west after retiring, and, with a group of investors, purchased the St. Paul Saints of the Western League. Comiskey and his partners then took the team to Chicago and joined up with the newly formed American League for the start of its inaugural 1901 season. The White Sox, as they would come to be known, won the first American League pennant, and led the league in runs and steals. In 1910, Comiskey oversaw the construction of 55,000-seat Comiskey Park, one of the first modern ballparks in the major leagues. During his tenure the White Sox won four American League pennants and the World Series in 1906 and 1917. In 1919, the team’s--and baseball’s--reputation was tarnished when eight White Sox players, allegedly fed up with the low salaries Comiskey paid them, conspired to throw the World Series in exchange for a payout from gambler Arnold Rothstein. After witnessing the strangely poor play of his players in the series, Comiskey reported his suspicions of corruption to Ban Johnson, the American League president. (Contrary to popular belief, the team’s "Black Sox" nickname came not from the black mark on their record for throwing the World Series, but from the fact that the frugal Comiskey made them pay for their own laundry.)
Comiskey was elected to the Baseball Hall of Fame in 1939. He died on October 26, 1931, at the age of 72.