Chicago Cubs: Five reasons the Cubs never became a dynasty

Chicago Cubs: The perfect guy for the job… until he wasn’t

Joe Maddon was the best manager the Cubs could have hired in 2015 and he was the best man for the job as he guided the team to the 2016 World Series. I don’t want to say that no one else would have been able to do it, but his ability to coax the most out of his players, especially soon-to-be stars like Willson Contreras and Baez, was second to none.

His ability to keep his players loose was unmatched. His ability to let the players do their own policing was all for the best with veterans like David Ross, Jon Lester, Miguel Montero, Jake Arrieta and John Lackey around the clubhouse.

He connected with the youngsters and let everyone be the best version of themselves. He impressed upon the team a few simple rules, but didn’t constrain or tyrannically oppress anyone. As noted, he was the perfect man for the job when the Cubs window of contention began.

Unfortunately something happened along the way and impediments sprung up. Whether those obstacles were with ownership, the front office, or talented young players not progressing as expected, we’ll probably never know for sure, but things weren’t working by the time 2018 and 2019 rolled around.

There’s also the matter of so many hitting and pitching coaches to go along with really successful teams, so that’s also a bit of a mystery. That being said, while I wasn’t a fan of letting Maddon go, it seems in hindsight that maybe the Cubs hung onto him too long.