The Chicago Bears are one of the most storied franchises in NFL history, but in recent decades, they’ve become a textbook example of organizational failure. From poor front-office decisions to failed quarterback selections, the Bears’ issues have compounded year after year, creating a franchise that’s not just struggling on the field but is trapped in a never-ending cycle of dysfunction. What’s even more concerning is that despite all the setbacks, it seems like the Bears haven’t learned from their mistakes. The reality is that the Chicago Bears are a bigger disaster than most fans—and even the league—are willing to admit.

A Quarterback Graveyard

For a team that prides itself on defense, the Bears have managed to completely bungle one of the most important positions in football: quarterback. The search for a franchise quarterback has been a never-ending saga, and it’s a search that’s been fraught with mistakes, bad luck, and desperation.

It all started with Jay Cutler, who was brought in with high hopes but never lived up to the billing. While Cutler had the arm talent to be a top-tier quarterback, his attitude and inconsistency kept him from being the Bears’ savior. His tenure was marked by missed opportunities, and despite setting franchise records for passing yards and touchdowns, Cutler never led Chicago to sustained success. The infamous 2010 NFC Championship Game, where Cutler was injured and left the game with a sprained MCL, only fueled doubts about his toughness and leadership. It was a sign of things to come.

After Cutler, the Bears made another blunder by drafting Mitch Trubisky with the second overall pick in the 2017 NFL Draft—passing on Patrick Mahomes and Deshaun Watson, who have since become two of the most accomplished quarterbacks of the era. Trubisky’s time in Chicago was a disaster, and the Bears’ inability to develop him as a franchise quarterback set the team back even further.

The Bears thought they could solve their quarterback woes by drafting Justin Fields in 2021. But three years into Fields’ career, it’s becoming painfully clear that the Bears are not setting him up for success. A porous offensive line, a lack of consistent coaching, and a failure to build a competent offense have all contributed to Fields’ struggles. Despite flashes of brilliance, Fields has been unable to develop into the player Chicago hoped for, and it’s hard to say whether it’s his fault or the result of poor organizational support.

Coaching Carousel: No Stability in Sight

Chicago’s coaching situation is another major issue. The team has cycled through three general managers and four head coaches in the past decade alone. Each time they seem to make progress, they find a way to derail it, often starting over with a new regime before the previous one can be given a fair chance to build something long-term.

After the departure of Marc Trestman in 2014—one of the worst coaching hires in recent history—the Bears brought in John Fox in 2015, hoping his experience would stabilize the team. But Fox’s tenure was a disaster, marked by a lack of offensive innovation and a failure to develop young talent. After Fox, the Bears brought in Matt Nagy, another failed experiment. Nagy, a former Andy Reid disciple, was supposed to bring offensive creativity to Chicago, but his offense was stagnant, and Trubisky never developed into a top-tier quarterback under his watch.

Now, with Matt Eberflus at the helm, the Bears are back at square one. Eberflus, a defensive-minded head coach, has shown little ability to improve the offense or develop young players. His tenure has been defined by bad decision-making, questionable personnel choices, and a lack of accountability. His staff has seen mass exoduses, with 13 assistant coaches leaving during his tenure, a sign that something is deeply wrong in the locker room. To make matters worse, the Bears have also failed to surround Eberflus with the right coaching staff, with many of the assistants who were let go quickly finding success elsewhere.

Front Office Blunders: The Curse of George McCaskey

At the heart of the Bears’ dysfunction is owner George McCaskey, who has presided over a decade of failure. Under his leadership, the team has failed to develop a clear and consistent vision for the future. The Bears have gone through multiple general managers, coaches, and coordinators, but none of them have been able to turn the franchise around.

McCaskey’s inability to make decisive, long-term decisions has left the Bears in a constant state of flux. His hiring of questionable general managers and coaches has been part of the problem. For example, in 2017, under then-GM Ryan Pace, the Bears traded up to the second overall pick to draft Trubisky, giving up valuable draft capital in the process. At the time, they bypassed Mahomes and Watson—two players who would go on to reshape the NFL. To make matters worse, McCaskey and Pace compounded their mistakes by hiring the wrong head coaches and failing to address key roster holes, especially along the offensive line.

While current GM Ryan Poles has made some positive moves, such as trading down to acquire DJ Moore and more draft capital in 2023, the Bears’ front office is still plagued by the same mistakes. Poles, much like his predecessors, will be judged by his ability to fix the quarterback position, and that responsibility will fall squarely on his shoulders in 2024. The Bears need a leader who understands how to build a team from the inside out and who can identify the right talent, not just rely on flashy moves that fail to address the core issues.

The Caleb Williams Dilemma: Another Mistake Looming?

Looking ahead to the 2024 NFL Draft, the Bears once again find themselves with a high pick—likely in the top five. The question is: who will they draft? If they decide to select Caleb Williams, the consensus “generational talent” at quarterback, they might find themselves falling into the same trap that they did with Trubisky and Fields.

Despite Williams’ accolades in college, he hasn’t exactly been a transcendent talent in his final season at USC. Some observers believe that Jaden Daniels, another quarterback in the 2024 draft class, is actually the better prospect right now, yet the Bears are likely to be swayed by Williams’ “generational” label. If they make this mistake, it will be just another chapter in the Bears’ long history of taking the safe, but ultimately wrong, choice.

The Bears also need to recognize that it’s not just about the quarterback. They’ve spent far too long ignoring the importance of building a solid offensive line, which is essential for any quarterback to succeed. They need a balanced approach to the draft, focusing not just on a shiny new quarterback but on surrounding him with the necessary pieces to succeed.

The Cycle of Mismanagement Must End

The Chicago Bears’ situation is a perfect storm of poor leadership, mismanagement, and bad decision-making. Every time they seem to make progress, they find a way to undo it. From the revolving door of quarterbacks to the constant turnover in the coaching staff and front office, the Bears have become a franchise defined by dysfunction.

As much as Bears fans want to believe that the team is on the verge of a turnaround, the reality is that until the Bears make smarter decisions at the top, they’ll continue to be stuck in the same cycle of failure. The Bears need leadership that can break this cycle—someone who can bring stability, make the right draft picks, and finally build a team that can compete for championships. Until that happens, Chicago will remain a bigger disaster than anyone wants to admit.