Jon Gruden still has his fastball, should the powers that be ever determine he’s employable again

Credit: WFLA

Jon Gruden will always be associated with Monday Night Football .

He spent nine years in that booth, most of them alongside Mike Tirico, before leaving to coach the Raiders in 2018. His last broadcast came that January, a Chiefs Wild Card loss to the Titans. On Saturday, the Chiefs were back, this time in a Buccaneers preseason game, and so was Gruden, calling a game for the first time in nearly eight years.

For the first time since 2018, Jon Gruden is calling an NFL game. pic.twitter.com/Tl5Y2oFAcg

— Awful Announcing (@awfulannouncing) August 23, 2026

Chris Myers usually handles the Buccaneers’ preseason play-by-play, and he still will for two of their three exhibition games this summer, against the Jets on Aug. 14 and the Jaguars on Aug. 28. But a scheduling conflict opened up the Chiefs game, and the Bucs gave the seat to Gruden — a play-by-play novice — pairing him with Ronde Barber in the WFLA booth.

Earlier this summer, Gruden revealed he has play-by-play ambitions , citing Frank Gifford as an example of a broadcaster who transitioned from analyst to play-by-play announcer, and the former NFL head coach thought he might be able to do the same.

And judging by the reaction Saturday drew, there’s clearly still an appetite for Gruden in a broadcast booth somwhere, preseason exhibition or not.

That’s LENGTH! pic.twitter.com/NmMSSC72oj

— Jon Gruden (@BarstoolGruden) August 23, 2026

“He’ll kick your Butker!”

69 Yarder from the Chiefs kicker!! pic.twitter.com/mC6NEeKmlU

— Jon Gruden (@BarstoolGruden) August 23, 2026

Jalon Daniels with a JOLT to Raymond James!

Great throw! pic.twitter.com/egvVzq1ZN1

— Jon Gruden (@BarstoolGruden) August 23, 2026

But settling that appetite for good is going to take more than a well-received Saturday night; it’s going to take resolving a lawsuit against the NFL that’s still grinding through Nevada’s court system. Gruden resigned as Raiders head coach in October 2021 after the Wall Street Journal and New York Times published emails he’d sent between 2011 and 2018, while working as an ESPN analyst, containing racist, misogynistic, and homophobic language, including remarks about former NFLPA executive director DeMaurice Smith and disparaging comments about Michael Sam’s 2014 draft selection as the league’s first openly gay drafted player.

The emails were part of a much larger haul the NFL had collected investigating workplace culture within the Washington Commanders organization; Gruden’s were among the small fraction of more than 650,000 emails that became public. He sued the NFL and commissioner Roger Goodell a month later, accusing the league of a “malicious and orchestrated campaign” to destroy his career by selectively leaking his emails while keeping the rest sealed.

The case has ground through Nevada’s court system for four years, including a stretch where the state’s high court initially sided with the NFL on moving the case into arbitration before Gruden’s team sought a rehearing. Gruden scored a real legal win last year when the state’s high court ruled, 5-2, that the NFL couldn’t force his case into private arbitration overseen by Goodell, the very man he’s suing, calling the league’s arbitration clause “unconscionable” as applied to a former employee. According to ESPN’s reporting , Gruden’s team has since moved to depose Goodell directly, along with a list of current and former owners that includes Jerry Jones, Bob Kraft, and Mark Davis, as well as longtime league counsel Jeff Pash and former Washington executive Bruce Allen, the original recipient of the leaked emails

In the last year, Gruden has had a cultural renaissance, parlaying a successful YouTube channel into a gig with Barstool Sports. After his name came and went as an outside candidate to potentially return to the NFL sidelines, he has been publicly politicking for a chance at a major college football job, saying he would “ die to coach in the SEC .”

None of that amounts to an actual offer, but it hasn’t dampened the appeal either way. Whatever comes next for Gruden, people are watching closely, and in the immediate future that means the Gruden Family Football Show , a new Barstool series pairing him with brother Jay this fall, an extension of the following he’s already cultivated there through Gruden’s QB Class and regular spots on Wake Up Barstool.

Momentum and access, though, are two different currencies, and a year of accumulating the former hasn’t bought Gruden any more of the latter. His path back to a prominent NFL broadcast booth remains complicated at best, and while Saturday settled that he still has his fastball, whether the powers that be ever let him throw it in a real game won’t be answered until the lawsuit is settled, at the very least.

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