Chicago Cubs: Three awful mistakes Theo Epstein made since 2016
Drafting and Developing
In the 2013 MLB Draft, the Houston Astros took Mark Appel with the first overall pick. He is one of the biggest busts in the history of sports but that left Kris Bryant available to the Chicago Cubs at the second overall pick. That was a home run for Theo Epstein and his staff as they attempted to build a winner through a tough rebuild. Bryant ended up being one of those guys that they built around and it led to a World Series title.
Since, then, drafting and mostly developing has been a problem. They drafted Kyle Schwarber with the fourth overall pick one year after Bryant. He is a good player but many better players were drafted after him like Trea Turner, Aaron Nola, and Matt Chapman who all turned out to be so much better. Schwarber might have more to give or he might not but it wasn’t a perfect pick by any means
They also have drafted Ian Happ, Brendon Little, Alex Lange, and Albert Almora in the first round as well since Theo came along. Happ and Almora have had their chances but neither of them looks like particularly good picks right now. They are hoping that Nico Hoerner can become something as their 2018 first-rounder but that even remains to be seen.
They have also been lousy at developing pitching under Theo. Pretty much every pitcher they had during their runs was brought in via trade after they were developed or signed in free agency. They have basically developed zero pitching through all of this. That is something they are going to need to fix and fast. Theo has done a great job at times throughout his Cubs career, but things haven’t been perfect in recent years.