25. Charlie Comiskey
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Sure, 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 a “world championship” (1886) with the St. Louis Browns during the mid-late 1880s. Comiskey posted an impressive .608 winning percentage in less than 10 years as a manager.