5 big mistakes the Chicago Cubs have made in recent years

5. The Contreras deadline situation

This is obviously the most recent Cubs mistake, and it was awkward for pretty much everybody. I think it's safe to say that almost everyone remotely close to the Cubs' orbit predicted he would be traded at the 2022 deadline. For weeks, Contreras had to answer questions about what it would be like to not play for the Cubs and how it feels to be traded by the only team he ever knew. His on-field production even dipped, and the Cubs did little to stop the bleeding because they knew Contreras was a hot commodity.

But when the deadline came and went, Contreras was still on the Cubs roster which was likely more surprising to him than anyone else. After being hung out to dry by the front office with little explanation, it's not surprising that Contreras accepted a 5-year deal with the Cardinals. Although reports later came out that a deal that would have sent Contreras to the Astros was shut down by Houston's ownership, perhaps this would not have even been an issue had the Cubs extended Contreras at some point.