Mike Matheny (275-211 career record, 1 pennant, 1 World Series appearance)
Joe Maddon (781-729 career record, 1 pennant, 1 World Series appearance, both with Rays)
Analysis: Joe Maddon is known for his funky road trip themes, and his prowess at the helm. Maddon has experience bringing young players along (see Evan Longoria, David Price, Chris Archer, Wil Myers), which is good news for a youthful Cubs team. Matheny is no scrub though, having been to the NLCS in each of his three seasons as manager, and to the World Series in 2013. Matheny has also done a nice job bringing his prospects along (Michael Wacha and Kolten Wong). Both are great managers, and both will undoubtedly be in manager of the year conversations.
Matheny’s short tenure has been impressive, but Maddon is practically a genius. He has a track record of success, and although he hasn’t had much success the last few seasons down in Tampa, many, myself included, think he can get the Cubs on the path to relevance.