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.