With struggling teams like the New York Jets and the Chicago Bears searching for new head coaches in 2025, the spotlight is back on Jon Gruden. With two division titles and an AFC Championship Game appearance with the Raiders, he boasts an impressive resume, after all. This, in addition to the Super Bowl title won by the Tampa Bay Buccaneers under him in 2002.
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On the Bussin’ With The Boys podcast, Gruden was asked which team he would like to coach in the 2025 season, given the opportunity. “The Bears with the young quarterback are interesting,” he responded, acknowledging the quality he sees in their rookie QB, Caleb Williams.
“When they lost Jaquon Brisker, they lost a key member of that secondary. But they have corners and some pass rushers. They need some receivers, man. And yeah, they’ve got a quarterback. I like this kid, man. This quarterback is interesting, man. He’s got me feeling nicey,” added Gruden.
Candidates such as Kliff Kingsbury (+250), Mike Vrabel (+400), Ben Johnson (+450), and Joe Brady (+500) top the odds for the coaching position for the Bears, alongside Gruden. Perhaps Jon’s dynamic presence and his interest in their rookie QB would prove to be hard for the Bears’ front office to ignore.
Gruden has a proven talent to rescue teams at the last moment and the Bears could make use of that. That talent came to Gruden and the Oakland Raiders’ rescue in their game against the Chiefs in the 2000 season. Gruden looked back and explained why that win remains a special memory in his coaching career.
Gruden revisits his favorite win against the Kansas City Chiefs
In a score reminiscent of the 2023 Super Bowl, the Raiders beat the Chiefs 38-35 in a memorable overtime win in 2000. This game was pivotal for Gruden’s coaching career. The Raiders overcame a 17-0 deficit to secure their first win against the Chiefs in 11 years.
“The calendar had just kicked over to 2000. I was in my second year coaching the Raiders. I was gonna get fired. We were 7-8. We were playing at the Chiefs. All the Chiefs needed to do was win the game, beat the Raiders they had beaten 100 times in a row, win the division, and get a home playoff game.” Gruden recalled.
Gruden explained that it was Rich Gannon’s 25-for-47 performance for 324 yards and three touchdowns that helped the Raiders salvage their season (8-8).
“We’re down 17-zip after about six minutes. And this place is rocking, man. My boy, Rich Gannon, got pissed off and shredded them. We beat them 38-35 in overtime. Check that game out. Raiders at the Chiefs 2000. Last game of the year. I was dancing on the field. Probably saved my job too,” Gruden concluded.
With Gruden’s excellent track record and willingness to work with Williams, the Bears could benefit from his expertise to develop their rookie talent next season.
However, it remains to be seen whether Gruden’s commitment to Barstool Sports will prevent him from coaching an NFL team.
