Jon Gruden discusses mixed feelings on leaving Raiders for Buccaneers

On July 17, 2026, Jon Gruden expressed regret about being traded from the Raiders to the Buccaneers during a podcast. He highlighted that the trade in 2002 stemmed from a contract dispute, despite ultimately leading to a Super Bowl win with Tampa Bay. Gruden reflected on the emotional nature of the decision, as he harbored strong ties to the Buccaneers. The trade involved significant compensation, including multiple first- and second-round draft picks. Gruden's tenure with Tampa Bay was marked by success, including becoming the youngest head coach to win a Super Bowl at that time, yet he returned to the Raiders later, resigning under challenging circumstances in 2021.

• 4:29 AMYahoo Sports — “I Didn’t Really Want To Get Traded”: Jon Gruden Regrets Leaving Raiders for Buccaneers Despite Winning a Super Bowl