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Reading: Bear Witness: Caleb Williams Must Ascend for Chicago to Reach Promised Land
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BigPaulSports > Blog > Game Analysis > Bear Witness: Caleb Williams Must Ascend for Chicago to Reach Promised Land
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Bear Witness: Caleb Williams Must Ascend for Chicago to Reach Promised Land

BigP
Last updated: 2026/05/29 at 7:21 PM
BigP Published May 29, 2026
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Bear Witness: Caleb Williams Must Ascend for Chicago to Reach Promised Land
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It’s natural to expect regression in the NFL.

When a team like the Chicago Bears ascends from last place all the way to 11 victories and an NFC North title with a second-year quarterback and first-year head coach, there tends to be skepticism about repeatability.  

If Caleb Williams and Ben Johnson are the real deal, though, the Bears’ orange and blue rocket ship could keep climbing.

“People see the win total at 9.5, and it might seem high,” Westgate SuperBook Vice President of Race and Sports John Murray told me. 

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“Chicago was a play or two away from the NFC Championship. Caleb looks like the real deal. We really like the coach. The division makes it difficult to get too carried away, but there’s no reason to think they won’t be good again.”

To Murray’s point about division strength, the Bears have the third-best odds (+370) to win the North at the SuperBook. Their NFL bookmakers have Detroit (+155) a smidge ahead of Green Bay (+180) with Minnesota (+700) a distant fourth. 

Chicago is essentially a coin flip to make the playoffs.  

Most optimism centers around Williams.

“If everything goes right, he’ll finish the season a top-10 quarterback,” “The Athletic” Bears writer Kevin Fishbain said. “Which means he’ll still be a playmaker but also a guy who improves his accuracy dramatically while continuing to avoid sacks and turnovers like we saw last year.”

Fishbain expects big things for receiver Luther Burden III, too.

My old WGN Radio teammate Mark Carman yaks about the Bears for CHGO these days, and he tends to keep level-headed thoughts.

“They should play [Tyson] Bagent,” Carman cracked.    

I told him I would print that if he was serious.

“Year 2 for Ben Johnson will come down to Year 3 for Caleb Williams,” Carman continued. “For the Bears to be more than a team that gets into the playoffs, Williams will need to be in the MVP conversation.

“The defensive line is highly unlikely to get enough pressure on the opposing quarterback, so the Bears’ quarterback is going to need to make another big jump and cement himself as one of the best in the game.”

Williams is 16/1 to win MVP — $1,600 on a $100 bet.

Most of Chicago’s playmakers are back, sans receiver D.J. Moore, who was traded to Buffalo. D’Andre Swift, Kyle Monangai, Rome Odunze, Burden, Jahdae Walker, Colston Loveland and Cole Kmet provide Johnson with ample chess pieces. Newcomers Kalif Raymond and Zavion Thomas will help.

Replacing retired center Drew Dalman won’t be easy, but the Bears clearly prioritized and addressed the O-line over the last two offseasons.

“Give them credit,” former NFL offensive lineman and current FOX Sports analyst Geoff Schwartz told me. “They had to find a replacement [for Dalman] and were proactive about bringing in Garrett Bradbury.”

Schwartz likes the stylistics the Bears’ big boys bring.  

“I love how they work in the run game,” he admitted. “With [Joe] Thuney as their anchor, they should continue to work together at a high level. They understand the purpose of the run, and they finish their blocks.”

Last year, I was all over the Bears to make the playoffs at +165.

This year, I like Over 9.5 wins (+110 at SuperBook). There’s lots to like with Williams having more seasoning and a better understanding of Johnson’s offense. Sure, the division and schedule are tough, but so are the Bears.  

Certainly, somebody in the sports betting streets must see the other side. Because all the positivity is exhausting. It can’t be all glass half full.  

“I lean Under on Chicago,” professional bettor Rob Pizzola said.

“But I’m scared to death of Ben Johnson.”

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TAGGED: nfl
BigP May 29, 2026
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