Considering everything he's been through, it's amazing Jon Gruden is only 61 years old.
The Sean McVay of his generation, Gruden was an NFL head coach at 34 and a Super Bowl champion at 39. The Tampa Bay Buccaneers fired Gruden 16 seasons ago. He spent nearly a decade on ESPN's Monday Night Football team, and the upcoming season will be the fourth since he resigned midseason from the Las Vegas Raiders as part of an email scandal that embroiled the NFL at the time.
Gruden was persona non grata across the football world at the time, but culture is in a different place in 2025 than it was in 2021. The New Orleans Saints brought Gruden aboard as a consultant in 2023, and the Bucs announced last month they will return Gruden to their Ring of Honor after removing him in 2021. Nowadays, Gruden has taken a gig with Barstool Sports, where he's expanded upon his "Spider 2 Y Banana" fame to become the entry point for verbose football play calls within the broader popular culture.
All that is well and good, but Gruden told the Fitz & Whit podcast he misses coaching and hopes to hop back in for one last ride.
“I miss it,” Gruden said. “I’m scratching that itch, though, right here — I’ve had more people come in here in the past few weeks than probably any coach in the league. College guys, NFL guys. I’m studying every day, scratching that itch. I would like one more chance to do it because I thought we had that team on the right trajectory. We were 3-0, we beat three straight playoff teams, and I thought we had a good young team and it really crushes me to see how everybody went different directions real fast. So deep down I’m kind of hoping someday I get a chance, but I’m definitely not counting on anything. So I’ve reinvented myself.”
The Buccaneers were 9-3 before a season-ending 4-game losing streak cost Gruden his job in 2008, and afterward the club enjoyed just two winning seasons (no playoff appearances) in the 11 years between firing Gruden and acquiring Tom Brady.
In his return to the Raiders, the club improved from four wins to seven to eight, and then was 3-2 upon his October 2021 resignation. That team made the playoffs, did not retain interim head coach Rich Bisaccia, and is now on its third head coach since after going 18-33 under Josh McDaniels and Antonio Pierce.
At the very least, the teams that have let Gruden go have immediately regretted it. Even in 2002, when the Raiders traded Gruden to the Bucs and lost the Super Bowl to him that very season.
Gruden is the same age as Mike McCarthy, so any franchise looking to scratch a "Super Bowl winner of yesteryear" itch would have to decide Gruden's expertise is so far beyond McCarthy's that it would be worth the round of blowback that would inevitable come hand-in-hand with his hiring.