Jon Gruden shows desire for a significant career shift

Jon Gruden Contemplates a New Direction

Jon Gruden is pondering a shift in his career path.

The ex-NFL coach, who has spent nine years as an analyst on ESPN’s “Monday Night Football,” is now eyeing a different role in the commentary world.

“I’ve been an anchor for nine years, and it’s just been really tough,” Gruden stated on the Ira Kaufman Podcast, noting his current position at Barstool Sports.

“I want to be the play-by-play man. You know, Frank Gifford made that transition. I want to try it out. I’ve been watching these guys—the likes of Mike Tirico—for years, and I think it’s time for me to give it a go,” he added.

Gruden’s tenure at ESPN lasted from 2009 to 2017, interspersed with his coaching roles first with the Buccaneers, then the Raiders.

Although fans appreciated him as an analyst, he often seemed emotionally reserved. This could have been an effort to keep friendly ties in the NFL, maybe in hopes of getting back into coaching one day.

It remains uncertain if this potential broadcasting role signifies the conclusion of his coaching journey, especially since, at 62, he was recently approached by the Jets to work with Aaron Glenn’s staff and there were rumors of a college coaching position, such as at the University of Arkansas.

“I really love football,” Gruden mentioned during an October 2025 appearance on “Pardon My Take.” “It’s about all I have. I’ve even dedicated resources to my office, setting up a server to keep all my movies and research together. Who knows what the future holds, but I’m always preparing for a coaching opportunity.”

However, there’s a significant obstacle Gruden must navigate before making the leap. He is currently embroiled in a contentious lawsuit against NFL Commissioner Roger Goodell.

Gruden has accused the NFL and Goodell of orchestrating a “malicious, coordinated campaign” by leaking emails that led to his resignation from the Raiders in 2021.

After facing backlash due to leaked emails containing homophobic and misogynistic language, along with critical comments about league officials, Gruden found himself permanently banned from football—until he made his return to the media landscape with Barstool in 2024.