Jon Gruden was the head coach when the Tampa Bay Buccaneers won their first Super Bowl in the 2002-03 season, and he’s one of the most beloved figures in franchise history. His name is enshrined in the team’s Ring of Honor for his contributions to the Buccaneers.
Despite being fired after the 2008 season, Gruden still pledges his allegiance to Tampa Bay and maintains plenty of connections within the organization.
He even returned to Raymond James Stadium on Saturday night to join Rondé Barber in the booth to call the Buccaneers’ preseason game against the Kansas City Chiefs. Gruden came away from his latest stop in Tampa Bay optimistic about Baker Mayfield’s contract situation.
Jon Gruden weighs in on Baker Mayfield’s Tampa Bay Buccaneers contract extension
The organization’s failure to get a deal done with Mayfield ahead of his training camp deadline has been frustrating for all involved.
Mayfield spoke to the media and said he felt disrespected by the team’s contract offer, and the organization reportedly wasn’t happy about how their quarterback publicly aired his grievances. Now, Mayfield is set to enter a contract year before potentially hitting free agency next March.
As often happens with contract negotiations, there’s been significant tension between Mayfield and the organization.
But you can count Gruden out when it comes to pessimism and panic surrounding Mayfield’s contract situation.
“I can’t speak like I have any inside scoop but I will promise you this: they are not very far away… I think everybody, every party included wants to get this done… And I think they’re a lot closer than people realize. But I would expect it to get done, indeed,” Gruden said during The Drive on 95.7 FM WDAE radio, via JoeBucsFan.
Gruden’s confidence in the negotiating process is for good reason. Despite a deal not being reached this offseason, one thing has remained consistent: Mayfield wants to sign a long-term deal to stay in Tampa Bay, and the Buccaneers want Mayfield to be their franchise quarterback.
Working out the financial and contractual specifics and coming to an agreement that works for both sides is a different story, but there’s reason to believe that a deal is going to get done eventually.
The Buccaneers are one of the best organizations when it comes to rewarding their own players with well-deserved contracts. If Mayfield plays at a high level throughout the 2026 season and leads Tampa Bay back to the playoffs, the organization should be happy to give him the long-term commitment he’s looking for.
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