Chargers vs. Raiders gets a weird prediction from Jon Gruden

Doug Engle/Florida Times-Union / USA TODAY NETWORK via Imagn Images

Most experts and oddsmakers seem to like the Los Angeles Chargers over the Las Vegas Raiders on the Week 2 edition of Monday Night Football. 

But not Jon Gruden. 

Gruden, who might be a tad biased as the former head coach of those Raiders, is now with Barstool Sports and put out a lengthy matchups and prediction piece. 

Appearing on a podcast alongside those predictions, Gruden stressed that he really likes what Pete Caroll does for football programs, never mind the fact that it happens to be his 74th birthday. 

“I like what the Chargers are. They are formidable. They are physical. They can run the football. But…it’s Pete Carroll’s birthday,” Gruden said. “You gotta get the attitude right in the locker room. Whatever you say about Pete Carroll, he gets the building feeling good. There’s a good vibe there right now. And I’m telling you, Geno Smith…is a lot better than people give him credit for.”

Back when I was coaching, the Chargers used to give me nightmares! Today, these Chargers are a physical bunch that will grind you down...

But don't forget about these RAAAAAIDERS on Pete Carroll's birthday! Should be a great game!@watchfoxone pic.twitter.com/CAi3pXWAKF

— Jon Gruden (@BarstoolGruden) September 14, 2025

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In his full prediction video, Gruden says the Raiders will escape with a win on a last-second field goal. 

Luckily for the Chargers, a guy by the name of Jim Harbaugh happens to be pretty good at turning around programs, too. And fans have seen that in action after the playoff appearance during last year’s “rebuilding” campaign. Now this year, too, with the win over the Kansas City Chiefs in Brazil. 

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Right now, the Chargers and Harbaugh are a step ahead of the Raiders in the rebuilding process, which figures to show on the field Monday night, hence Gruden’s prediction being rather unique this week.

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