Charles Comiskey
Charlie Comiskey is almost entirely recalled today as the pinch-penny owner of the 1919 Chicago White Sox of “Eight Men Out” fame. Subsequent research has established that motif to be largely fiction – Comiskey was actually relatively generous with his players by the standards of that era – but hey, it holds the movie’s plot together and Comiskey’s been dead since 1931 so who really cares?
As with Mack, Comiskey’s visibility as an owner obscures the fact that in his he was a superb player, arguably good enough to have been elected to the MLB Hall of Fame for his on-field accomplishments alone.
Comiskey got his professional start as a 22-year-old first baseman with the St. Louis Browns of the fledgling American Association, a circuit created in 1882 as a rival to the National League. Quickly demonstrating his leadership skills, he was appointed player-manager just one season later, leading the Browns to their first of four consecutive pennants starting in 1885. In 1886 his Browns beat the White Stockings in the third World Series.
Comiskey played through 1894, his best season being 1887 when he batted .335. A close friend of Johnson, Comiskey got the Chicago franchise when the American League was created in 1901, and his team won the inaugural AL pennant.
The Sox repeated as AL champs in 1906, and went on to win the World Series. They won a second World Series in 1917 before their date with infamy in October of 1919.
Comiskey continued to own the team until his death when control passed to his son and other members of the Comiskey family.