Jon Gruden has a deep history with the Raiders dating back to the franchise's days in Oakland. He had two stints as the organization's head coach, including one where he led the team during their move to Las Vegas.
Both of his tenures ended unceremoniously, as he was traded to the Tampa Bay Buccaneers ahead of the 2002 season to end his first stint. More recently, Gruden was forced to resign partway through the 2021 season after a controversy with his personal emails.
At the time, it appeared that Gruden's coaching career was over. However, he has recently re-emerged in the limelight, leading many to believe that he could land a job in the future. Gruden has also repeatedly expressed his desire to get back to coaching.
Jon Gruden would reportedly be interested in returning to the NFL to coach the Giants
It once seemed like a long shot that Gruden would ever coach in the NFL again; however, his role at Barstool Sports and winning various legal proceedings against the league have seemingly changed that perception.
His younger brother and former NFL head coach, Jay Gruden, appeared on The Arena: Gridiron, where he revealed that the elder Gruden would be interested in the New York Giants' head coaching vacancy after Brian Daboll was recently fired.
"I think he'd be very interested. He loves football. He loves Jaxson Dart. If you have a young quarterback as talented (as) Jaxson, you want a guy like Jon who's going to challenge him every day," Jay Gruden said. "Does [Jon] have some stuff in his background? Maybe he does, but if you want a guy that gets the most out of your quarterback, the most out of your team, then I believe Jon Gruden would be a good fit."
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He added that he doesn't believe his older brother ever felt that his NFL coaching career was truly over, despite being down when he initially resigned from the Raiders. Jon Gruden previously discussed his interest in returning to the sidelines, jokingly suggesting that he would bring Derek Carr in as his quarterback.
While the Giants certainly wouldn't allow that to happen just one year after drafting a quarterback in the first round, it leads to questions about what he would truly bring to a franchise. Gruden's second tenure with the Raiders was defined by his struggles with properly evaluating and landing talent.
His mistakes in decision-making and drafting have continued to hurt the franchise four years after his departure. During the four seasons Gruden was in charge, the Raiders had seven first-round picks. Josh Jacobs is the only one of those players to be named a Pro Bowler or All-Pro, while Kolton Miller is the only player still on the team among those he drafted on Day 1.
Gruden was not terrible in his second stint as the Raiders' coach, but he was not great, either. The team did show signs of improvement despite his not being able to see it through. If he does land another NFL gig, it's at least clear that he should not have control of personnel decisions.