Derek Carr spent nine seasons under center for the Oakland and Las Vegas Raiders, with Jon Gruden serving as his head coach for parts of four of those years. The duo was in place as the franchise shifted from Oakland to Las Vegas.
Their tenure together, however, is often remembered for its failures. Most notably, how it unceremoniously ended due to leaked emails, their inability to reach the postseason together and an unprecedented amount of reaches in the first round of the draft.
Something that is often overlooked, however, is that the team's winning percentage continued to improve each year, right up until Gruden's resignation five weeks into the 2021 season. While Carr led the team to a postseason appearance in 2021, he lasted just one more season in Las Vegas.
Jon Gruden reveals details of Raiders' partnership with Derek Carr
He landed with the New Orleans Saints, but after just two seasons, the four-time Pro Bowler announced his retirement during the offseason. He recently reunited with Gruden on his podcast, where his former coach discussed the nature of their relationship during their time with the Raiders.
Gruden and Carr have both entered the media space since leaving the NFL. The duo appeared on the latter's Home Grown podcast, which he hosts with his older brother David Carr. Gruden told a story about Derek, which will not surprise Raider Nation in the least.
"Derek was a great leader. He didn't cuss and yell at the players a lot, either. He did it in a very positive, constructive way. There were times I'd say, 'Hey Derek, I'm going to get on your butt today. I am going to chew you out. Bad". Because that'll give him the freedom to really start chewing out some of the guys I wanted to be chewed out," Gruden said. "So, I would start yelling at him, and it was bad. I'd be on the field with my walkie-talkie screaming at him, throwing my visor and Derek would start yelling at the players. It was really pretty cool. We had a great, trustworthy relationship. I trusted him with everything."
Welcome Home Jon Gruden!@derekcarrqb reunites with his old @Raiders head coach @BarstoolGruden to examine the importance of trust between NFL coaches & quarterbacks.
— Home Grown (@HomeGrownTweet) September 24, 2025
New Episode Out Thursday on YouTube 📺 pic.twitter.com/PLrL6HfgRn
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Fans can say what they want about Carr's ability on the field, but the consensus has always been that he is a good person and leader, and there was no doubt that he loved the Silver and Black.
While Gruden and Carr were unable to reach the postseason together, the nature of their relationship has always been clear. It has been widely reported, and recently confirmed by Mark Davis, that the former head coach even opted to pass on signing Tom Brady due to his belief in Carr.
Gruden later took a consultant role with the Saints to help Carr's new coaching staff get acclimated to him. While the long-time Raiders quarterback was considered divisive to the fanbase due to his performance on the field, it is difficult to argue with Gruden's assessment of him.