There was a time in 2009 when Jay Cutler strolled into Chicago like the guy who just found the aux cord—full control, full season, not a single start missed. Chicago thought they’d finally locked in their franchise guy. And let’s be real—they kinda did. Years after, Cutler is still the franchise’s leader in passing yards, passing touchdowns, attempts, and completions. But then came the never-ending QB carousel: new faces, false hopes.

From Mitch Trubisky’s rollercoaster tenure to Justin Fields‘ flashes of brilliance, the Bears have been on a wild ride. And now? Caleb Williams has taken the reins, and let’s just say his first season was a mixed bag. For starters, the second-year QB became the first quarterback in the franchise’s history to start every game and inked his name for numerous franchise records. But let’s not sugarcoat this.

Because his numbers tell a different tale. 17 starts, and by the time his rookie season wrapped up, the track record showed 5-12 against his name. And oh, along the way, he did rack up some pretty numbers—over 3,500 yards, 20 TD, and he even notched up nearly 500 rushing yards. But the highlight of his rookie season?

Yeah, you guessed that right. Those league-high 68 sacks. So, the big question is: What’s that one thing he could change in his second year? That’s where the Bears‘ legend Devin Hester comes in, who recently stopped by at Up & Adams Show. When Adams asked, ” Is there anything you’d like to see from him (Caleb) in the second-year?” Hester gave a pretty great solution. “I would say, just get rid of the [foot]ball a little quicker,” he said.

“I know he makes plays with his legs, but I would say, like you say, holding the [foot]ball a little bit, sometimes you got to let it go. I would say, make a decision a little faster this year.” Maybe that’s where the whole “legs first, think later” approach bit him. Like yeah, 489 rushing yards are cool and all—but sometimes it felt like Caleb thought he was in a Madden scramble challenge. The guy would take off, skip the check-down, and next thing you know—bam, sack city. That hesitation? Yeah, it cost him.

But let’s call it what it is. The guy was in his first year in the pros. You can’t expect him to pull out some TB12 stuff. The guy’s coming after a learning rookie season, and Devin Hester believes that the Williams will grow with experience. “I think that comes with the experience from last year of the speed of the game,” he continued. “This year, if he can get rid of the [foot]ball a little quicker, making the decision a little quicker is my answer. Get rid of the [foot]ball a little quicker. Make the decision quicker… And Sky’s the limit for him.”

To make it more interesting, the Bears just hired the offensive guru—Ben Johnson as their head coach. You can just say Caleb Williams just got the right guy to develop under. And it looks like the head coach has started preparing his quarterback for what lies ahead.

A challenging start for Caleb Williams under Ben Johnson

Here’s the deal: Caleb Williams had a notable season when it comes to the numbers. But that fairy-tale ending for the Bears? That’s the tricky part. During his first six weeks in Chicago, Williams led his team to a train-wreaked 4-2 start. Enter week 7, and the QB and the team surely thought to flip the scripts. But Jayden Daniels and the Commanders said no, and that week 7 loss kick-started the Bears’ 10 game losing streak.

No wonder amidst this chaos, the HC Matt Eberflus and OC Shane Waldron were fired. Fast forward to now, and there’s a new regime in Chicago. The one led by offensive guru, Ben Johnson, who landed in Chicago after a tremendous three-year stint with the Detroit Lions. And now Williams made it clear that he wants his HC to challenge him. “Us growing together is key. Starting now. Him pushing me [is] key,” Williams said of Johnson. “I know that, and he knows that.”

And looks like Ben Johnson fulfilled his demands, but not in the way he’d expected. We aren’t talking about the on-field grind. Oh no. In fact, the HC rolled into the QB room on Day 2 of OTAs, firing off questions like a kid who just found out there’s a pop quiz. “Today we had our first quiz in the QB room,” Williams said.

“We went over a few things yesterday, talked about a few things and Ben walked in this morning, flung open the door, made a grand entrance and then we got to work, him testing us about what we talked about yesterday. Already first day in and challenging us. Everybody loves a challenge in this sport. It’s one of the great things about this sport. Every day is a challenge and today we got our first one.” See, Ben Johnson surely knows a thing or two about coaching a QB, considering the man led the Lions to three consecutive top-five finishes in points and yards per game.

Now that he joined the Bears, he was asked for just one thing: to change the Bears’ offense that ranked 26th in offensive EPA last season. The vibe is good. The odds are favoring Ben. Now it’s up to Williams and his crew to turn the table in the 2025 season.