The Joe Maddon Cubs era was one for the ages, but how should we remember his time in Chicago and that core's legacy? David Kaplan, Tim Stebbins, and Tony Gill discuss Maddon's importance to the Cubs and why he ultimately left if he wanted to stay. The crew also discusses the players on those teams the Cubs parted ways with after Maddon.

(2:40) - Joe Maddon returns to Chicago and says he didn't want to leave the Cubs

(10:00) - How should the Joe Maddon Cubs era be remembered?

(19:00) - Is it disappointing the Cubs didn't win more World Series after 2016?

(27:00) - Should players test free agency or should they take whatever extension the team gives them?