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Jon Gruden's embarrassing Bears take couldn't have aged any worse

ByChris Pownall
Aug 6, 2026; Tampa, FL, USA; former Tampa Bay Buccaneers coach John Gruden talks to media before training camp at AdventHealth Training Center. Mandatory Credit: Nathan Ray Seebeck-Imagn Images
Aug 6, 2026; Tampa, FL, USA; former Tampa Bay Buccaneers coach John Gruden talks to media before training camp at AdventHealth Training Center. Mandatory Credit: Nathan Ray Seebeck-Imagn Images | IMAGN IMAGES via Reuters Connect

Jon Gruden probably wishes his latest Chicago Bears breakdown had been released a little sooner.

The former NFL head coach appeared on the Gruden Family Football Show to preview Chicago's Monday night matchup against the Seattle Seahawks. While he had some encouraging things to say about Caleb Williams and Ben Johnson, his assessment of the Bears' defense was considerably less flattering.

Unfortunately for Gruden, the timing couldn't have been worse.

Chicago's acquisition of Jeffery Simmons suddenly made one of his biggest criticisms look rather foolish.

Jon Gruden's Bears take overlooks a rapidly improving defense

Gruden spent much of the discussion praising Seattle's defense, particularly its ability to frustrate opposing quarterbacks. He pointed to the Seahawks' recent performances against Denver and Kansas City as evidence that Williams could be in for a difficult evening.

Then the conversation shifted to Chicago's defense.

"The Dennis Allen, no pass rushers. I mean, Sweat hasn't played," Gruden said.

He continued by acknowledging something that seemingly contradicted his own criticism.

"I say they don't have any pass rushers, but they've had two or more sacks in every game."

That's an interesting way to dismiss a defense that keeps finding ways to pressure quarterbacks.

Gruden even praised Allen's creativity, pointing to his blitz packages and disguised coverages. He mentioned Kyler Gordon's remarkable sack production and acknowledged how effectively Chicago has manufactured pressure.

So which is it? Does Chicago lack the personnel to get after quarterbacks, or has Allen developed a defense capable of producing consistent pressure regardless of who's available?

Apparently, both.

Of course, there's another problem with Gruden's assessment.

The Bears acquired Simmons from Tennessee, giving Allen an established interior defensive lineman who can create pressure without requiring additional blitzers.

To be fair, Gruden's segment appears to have been recorded before the trade. That's an important distinction. Still, releasing the breakdown after Chicago addressed the very weakness he identified makes the criticism look spectacularly outdated.

Gruden also questions Bears rookie Colston Loveland

Gruden wasn't finished identifying potential problems for Chicago.

He also questioned whether the Bears could establish their physical running game without Cole Kmet, suggesting that Loveland wasn't particularly effective as a blocker.

"Loveland's not a great blocker, so they're going to have to find an answer," Gruden said.

That's another assessment Bears fans might reasonably challenge.

Loveland's development has been an important part of Johnson's offensive plans, and reducing his contributions to a perceived blocking deficiency ignores the versatility Chicago wants from its tight ends.

Gruden ultimately picked Seattle, predicting a difficult night for Williams against Mike Macdonald's defense.

There's nothing particularly outrageous about choosing the Seahawks at home. They're a formidable opponent, and Chicago will face a legitimate challenge.

But Gruden's defensive assessment is another story.

The Bears were already generating sacks before Simmons arrived. Allen was finding ways to create pressure despite personnel limitations. Now Chicago has added another significant weapon to that equation.

Gruden might ultimately get his prediction right. Seattle could very well win Monday night.

But if the Seahawks struggle to protect Sam Darnold against Chicago's revamped defensive front, his comments about the Bears having no pass rushers are going to sound even worse.

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