Chicago Cubs: Three huge mistakes that led to this rebuild

Of course, during their run, the Cubs had some good pitching. Guys like Jake Arrieta, Jon Lester, Kyle Hendricks, John Lackey, Jose Quintana, Tyler Chatwood, and Yu Darvish were all there for them from 2015-2020. The crazy thing is that the Cubs didn’t draft any of those guys (or find them as international prospects).

All of them were acquired in a trade or signed in free agency. Kyle Hendricks only ever played for the Cubs but they acquired him in the Ryan Dempster trade. You can give them credit for developing him if you want but even one guy out of all their prospects isn’t very good.

The Cubs have done a very lousy job of developing pitching throughout this era. That forced them to spend money on pitching more than they should have. They traded Dylan Cease for a pitcher who is older, has fewer years of cheap control, and is simply not as good of a pitcher in the long term. To be honest, we can’t even be sure that Cease would have developed well with the Cubs. The jury is still out on him right now but the White Sox are so much better at developing pitching.

If the Cubs were better at developing pitching, they probably wouldn’t have needed to sign Tyler Chatwood to a bad contract. They might have not needed to trade Jimenez for Quintana. They might have been able to keep Yu Darvish to try and win a World Series with him. It is clearly something that this franchise needs to fix if they ever want to become a winner again. They are rebuilding and these are three clear reasons why.