The Chicago Bears May be Bad, but They’re Historically Good at This
Will Caleb Williams Suffer The Same Fate As His Predecessors? History Says Yes.
The Chicago Bears suck, yet I will always be a fan. Why? It’s beyond me, but I can’t imagine ever rooting and being a die-hard for another team. The McCaskey’s wouldn’t have it any other way. Imagine being a business owner and not caring about the product you sell, yet customers still buy that product. You bring in millions! It’s the perfect business model and the McCaskey’s will NEVER sell the team.
Anyways…let’s talk about what The Bears don’t suck at, that is, ruining 1st round QBs.
Jay Cutler
Drafted: Rd 1, #11 - 2006 NFL Draft
Traded to Bears: 04/02/2009
Cutler was a pro-bowler in 2008 and seen as the franchise savior for The Chicago Bears in 2009.
Then the Bears did what they do best, they completely wasted him.
How They Ruined Him:
Cutler came in with a rocket arm, confidence, and just enough swagger to survive in Chicago. The problem? The Bears gave him zero protection. NONE.
He was sacked 252 times in 8 seasons. That’s an average of 31.5 sacks per year. By the time the Bears finally tried to fix the offensive line, Cutler’s internal clock was shot.
The coaching carousel didn’t help either. Cutler had to endure Lovie Smith, Marc Trestman, and John Fox—three entirely different offensive systems in eight years. Zero consistency. Zero stability.
Weapons? Early in his career, Cutler had to throw to guys like Devin Hester, who was a great returner but not an actual receiver. It wasn’t until Brandon Marshall showed up that Cutler finally had a real target.
The Fallout: Cutler’s career in Chicago was defined by glimpses of greatness overshadowed by dysfunction. He’s still the franchise leader in most passing categories, which is more of an indictment on the Bears than an achievement. He never lived up to his potential—not because of talent, but because the Bears set him up to fail.
Final Goodbye: Cutler was released in 2017 after eight exhausting seasons. He left Chicago broken, criticized, and labeled as apathetic. But can you blame him? The Bears broke him down and then acted surprised when he stopped caring.
Now let’s talk about the next victim…
Mitch Trubisky
Drafted: Rd 1, #2 - 2017 NFL Draft
Picked by Bears: 04/27/2017
Trubisky was supposed to be “the guy.” The quarterback to end all quarterback problems. Instead, he’s another chapter in the Bears’ long history of letdowns.
How They Ruined Him:
Let’s start with the obvious—the Bears drafted Trubisky over Patrick Mahomes and Deshaun Watson. That decision alone haunted him before he even took a snap.
Matt Nagy was billed as a quarterback guru, but his offense was anything but innovative. Nagy refused to adapt to Mitch’s strengths—quick throws and mobility—and forced him into a system he didn’t fit.
The offensive line was a disaster, forcing Mitch to play scared and run for his life more often than not.
Lack of weapons? Check. Outside of Allen Robinson, Trubisky had no consistent playmakers. His supporting cast was about as reliable as a Bears lead in the 4th quarter.
Confidence killer? Absolutely. Nagy benched him for Nick Foles in 2020, sending the message that the franchise had given up on him.
The Fallout: Trubisky’s tenure ended with a whimper. After four up-and-down seasons, the Bears declined his fifth-year option. He walked away in 2021, labeled a bust, even though the Bears never gave him a chance to succeed.
Final Goodbye: Trubisky left Chicago broken, just like Cutler. Drafted too high, coached too poorly, and given too little help. Now he’s a backup elsewhere, while Bears fans are stuck wondering what could’ve been if the team actually knew how to develop quarterbacks.
And speaking of quarterbacks who deserved better, let’s move on to Justin Fields…
Justin Fields
Drafted: Rd 1, #11 - 2021 NFL Draft
Picked by Bears: 04/29/2021
Justin Fields was supposed to be different. He was supposed to break the curse. Instead, the Bears did what they always do—they ruined him.
How They Ruined Him:
Fields came in as a dual-threat quarterback with elite athleticism and arm talent, but the Bears refused to build around his strengths.
He was thrown behind one of the worst offensive lines in the league, where he’s already been sacked 130+ times in just three seasons. Sound familiar?
Matt Nagy failed him in his rookie year with no development plan. Then Luke Getsy showed up and made it worse—constantly trying to turn Fields into something he’s not.
The Bears surrounded him with practice squad-level receivers until DJ Moore arrived in 2023—too little, too late.
The offensive scheme? Vanilla. Predictable. Outdated. Fields was never given the tools or freedom to maximize his abilities.
The Fallout: Fields has flashed brilliance. He ran for 1,000 yards, made jaw-dropping throws, and carried this offense at times. But it didn’t matter. The Bears failed him so badly and the whole world knew they would draft Caleb Williams.
Final Goodbye? In the 2024 offseason, the Bears traded Fields to the Pittsburgh Steelers and drafted Caleb Williams as their new hope. Fields left Chicago as another talented quarterback chewed up and spit out by this franchise.
And that brings us to the next question: Is Caleb Williams next?
Caleb Williams
Drafted: Rd 1, #1 - 2024 NFL Draft
Picked by Bears: 04/25/2024
Caleb Williams is the latest quarterback savior brought in to fix what decades of mismanagement have broken. He’s got the arm talent, mobility, and swagger to be a star. But does he have a franchise that can actually support him?
The Question Marks:
Will the Bears finally build an offensive line that can protect their QB?
Will they get the GM right?
Will they get the coaching staff right?
Will they get the "culture" right?
The Reality Check: Williams has all the tools to succeed, but this isn’t about him, it’s about the Bears. Can they finally get it right? Or will Caleb join Cutler, Trubisky, and Fields on the list of quarterbacks Chicago wasted?
Only time will tell, but history isn’t on their side.
Will History Keep Repeating?
The cynic in me says yes. The Bears fan in me says yes.
That said, Caleb Williams appears to be built differently and is making plays I’ve never seen a Bears QB make. He’s the only superstar this team has and I hope the organization recognizes that.
I hope they build around him. Not with players, but with new coaching and a new front office. They simply don’t have the foundation in the place, and this dates back to the Cutler era and likely before that. The Chicago Bears need to get the foundation right.
If not by strategic moves, If not by intent, then by sheer luck.