26. Charlie Comiskey
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Sure, Charlie Comiskey’s legacy has been tarnished over the 1919 Chicago Black Sox scandal, but he was a fine manager before that debacle. Comiskey won four pennants and the 1886 World Series with the St. Louis Browns between 1885-1888. Comiskey posted an impressive .608 winning percentage in less than 10 years as a manager. Overall, Comiskey’s team finished with a winning record in 11 of the 12 seasons he was in charge. After his Cincinnati Reds went 55-75 in 1894, Comiskey retired with a managerial record of 839-540.