3 Biggest Mistakes the Cubs Made Under Theo Epstein's Tenure

The Chicago Cubs achieved the ultimate MLB goal of winning a World Series back in 2016. That gave fans high expectations thanks to the actions and words of Theo Epstein, however, it's been far from smooth sailing since.

A few mistakes along the way have the Cubs in a state of transition heading into 2020. Here are three of the most glaring.

3. Letting Dexter Fowler Leave

Dexter Fowler headed to St. Louis on a five-year deal in 2017. / Michael B. Thomas/Getty Images

Dexter Fowler was on the 2016 World Series squad and was among the team's best players that season. Epstein, after not signing Fowler until Spring Training of that year, let his starting center fielder and leadoff man walk to the division-rival Cardinals. While $82.5 million is certainly a lot of money, it's hard to put a price tag on a guy who helped ignite the offense for a majority of the season. Ever since then? The Cubs have been searching for a consistent center fielder and leadoff hitter.

2. Not Trading Kyle Schwarber After 2016 World Series

Kyle Schwarber could have fetched a nice return in a trade. / Quinn Harris/Getty Images

Epstein could have moved Kyle Schwarber and received a nice return based on the years of team control remaining on his contract and his gutsy performance in the World Series after coming back from a torn ACL. It's been years, and Schwarber clearly has no place on this team. He's a liability in the field and has strayed FAR away from his primary catcher position. Schwarber is an AL player considering he best fits in most lineups as a DH. Keeping him this long and not supplementing other aspects of the roster was a mistake.

1. Never Properly Fixing the Bullpen

Craig Kimbrel got a lot of money without providing the best results in 2019. / Nuccio DiNuzzo/Getty Images

Epstein threw $43 million at Craig Kimbrel last year to become the face of the bullpen. The closer responded with a 6.53 ERA and only 13 saves. He didn't sign until June and dealt with injuries as well. Not only that, but this was pretty much the only momentous move the front office made to fix an inconsistent and largely ineffective bullpen -- and it was a bad one. Years of relying on guys like Pedro Strop and Carl Edwards in addition to patchwork signings like Brandon Morrow and Tyler Chatwood have doomed the team's relief corps. How they didn't upgrade better after their World Series win, we'll never know.