The Chicago Bears made a splash at head coach by bringing in former Detroit Lions offensive coordinator Ben Johnson, but with him coming to town, quarterback and former No. 1 overall pick Caleb Williams might be in for some tough coaching.
In fact, according to NFL Network’s Ian Rapoport, it could be “miserable” and the plugged-in analyst doesn’t think Williams truly understands “what it’s going to be like.”

Ian Rapoport’s Comments on Caleb Williams’ ‘Miserable’ First Year With Ben Johnson
On “Good Morning Football,” Rapoport started his comments by saying, “So, look, Caleb Williams said all the right things, and I think he has and will continue to do so—wants Ben Johnson to challenge him, wants this offensive coaching staff to challenge him—it’s going to be really hard.”
This makes sense. When the Bears drafted Williams, and Matt Eberflus was the head coach, it seemed a bit more accommodating, whereas Johnson has his plan and will stick with it.
We have seen many coaches come into new situations with big plans in the past only to see them fail because they are unable to work with their quarterback by bringing them into a system that’s simply not a fit. However, this is one of those situations where Johnson’s system will benefit Williams, and challenging him is good.
“I know he’s ready. I know he thinks he’s ready. But I don’t know if he truly understands what it’s going to be like,” Rapoport said on April 9. “Just, to go from good—and Caleb Williams was good last year, certainly had his moments—kept the ball out of the hands of the opponent… kinda kept some drives moving, probably took too many sacks, got a little too beat up.
“So, there was certainly some good there. But to be great, to be one of the actual greats, which his talent should allow him to do … it is going to be really miserable.”
In-studio on @GMFB: #Bears QB Caleb Williams may be miserable this year… and that’s a good thing. pic.twitter.com/36ZdaMMHPj
— Ian Rapoport (@RapSheet) April 9, 2025
Ben Johnson: Not ‘Most Pleasant Person’
It’s safe to say that Johnson could be the toughest coach Williams has worked with.
In college, the talented quarterback was with Lincoln Riley at Oklahoma then followed his head coach over to USC. Those two men shared a healthy relationship, with Riley delivering words of encouragement to Williams during his up-and-down 2024 rookie campaign.
“Keep going,” Riley told Williams, via ESPN’s Courtney Cronin.
That kind of positive reinforcement might be lacking with his new head coach in Chicago. According to Rapoport, Johnson’s demeanor isn’t always warm and fuzzy.
“Ben Johnson has been incredibly successful in Detroit. Is he the most pleasant person to be around during the season? I don’t think he is,” Rapoport said. “It’s going to be hard. And I don’t even know if right now Caleb Williams understands, but, like, on Monday night in November—it’s going to suck, and if you want to be great, it has to suck.
“And so, yeah, it’s all smiles now, he’s out there, he’s lookin’ cool, it’s a lot of positivity. To get where they need to go, he has to embrace being absolutely and utterly miserable.”
PFSN’s Latest Bears Draft Pick Projects
In PFSN’s latest three-round mock draft, draft analyst Reese Decker projects the Bears will draft these players:
- No. 10 overall: TreVeyon Henderson, RB, Ohio State
- No. 39 overall: Nic Scourton, EDGE, Texas A&M
- No. 41 overall: Aireontae Ersery, OT, Minnesota
- No. 72 overall: Kevin Winston Jr., SAF, Penn State