Chicago Bears: 5 Biggest Regrets from the Past Decade

Every franchise has that period in their history. That time where they repeat the same phrase, “Can we just do that over again?” The Chicago Bears understand.

They’ve been enduring that sort of relentless misery for the better part of 10 years. So many moments have come and gone where many in the organization must mumble a silent prayer for a do-over. The question is can these moments be narrowed down into a list? Which among them stand out as the worst of the bunch and why?

A few factors go into this. How bad the decision was from the start and both the short and long-term negative impact it had on the franchise. It should make for a fun debate as to whether fans agree with the rankings or if they’d go in another direction. What better way to start things off than with the most recent addition on the the list.

#5:  Signing Mike Glennon

The logic behind signing Glennon was relatively sound. It was obvious the Bears would still draft a quarterback but they wanted to hedge their bets. So they sought out a veteran to compete for the job. Glennon was the choice. That wasn’t the problem. In was the enormous contract they handed him at a whopping $18 million in guarantees. Even then people felt they overpaid.

If they wanted veteran competition with Mitch Trubisky, they easily could’ve gotten somebody like Case Keenum or Ryan Fitzpatrick. Both were available at the same time Glennon was and both ended up having better records in 2017 than he did. That money could’ve then been used at other positions of pressing need including offensive tackle with guys like Russell Okung and Rickey Wagner available.