3 Theo Epstein mistakes that ruined Cubs’ chance at a dynasty

3. Waited too long to make change

The Chicago Cubs waited too long to make a change to their offensive lineup.

It was so obvious that the Chicago Cubs were gasping for offense after the 2018 season was over. Theo Epstein literally admitted that it was a broken offense and he did nothing to correct it in the long term. He let it ride out because of what guys did when they were in their early 20s.

The Cubs probably should have shaken things up with one of Kyle Schwarber, Javier Baez, Anthony Rizzo, or Kris Bryant after that season. If it is broken, you are allowed to try and fix it. It was ridden out too long and the CUbs are suffering for it now.

After 2020, they let Kyle Schwaber walk for nothing. In 2021, they traded Anthony Rizzo, Kris Bryant, and Javier Baez because none of them were worth resigning. None of those trades were made by Theo either because he left town with one year left on his contract.

If the Cubs would have done something to spark their offense by making a trade after 2018, they probably wouldn’t be on pace for 100 losses right now and most of their core might still be locked in. Chalk that up as a huge mistake.

It is unclear how much these mistakes hurt them in the long term but if Theo was a lot smarter after winning in 2016, things would be different for the organization right now. He left them in a hard spot and it will be a while before they are good again.