Since 1903, when the postseason was modernized similar to how it is today, only 11 of 60 managers have been able to lead the Chicago Cubs to a postseason berth. Joe Maddon and Frank Chance are the only two managers in the organization’s history to win a World Series.
This list before you is a ranking of the top five managers in the 144-year history of the Cubs. The list is compiled of post-1900 managers. Cap Anson was one of the team’s early managers, leading them from 1879 to 1897.