As such - and especially with Saturday afternoon's playoff game featuring one of the Raiders' division rivals, the Chiefs - fans on social media and at Arrowhead Stadium were quick to poke fun at the situation, as well as Gruden's reported 10-year deal and worth an estimated $100 million.
Hours after the game, the Oakland Raiders made it official by sending out tweet and press release.
"It's an emotional and bittersweet day for our Monday Night Football family as today we say goodbye to coach Gruden after nine very distinguished years in this Monday Night Football booth".
"Well, thank you, nothing's official yet, but these Chiefs fans have been on my case since I got here", Gruden said. Oakland traded him to Tampa Bay after the 2001 season, and the following season he guided the Buccaneers to their only Super Bowl title - a game in which they beat the Raiders.
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He last coached with the Buccaneers, with whom he won Super Bowl XXXVII - beating the Raiders 48-21. Could he be the man to replace Gruden on ESPN?
While you may or may not be familiar with his work, or who he is, here's five things you should know about the team's newest Head Coach.
"Coach. great legacy on 'Monday Night Football, ' not only have you lived up to it, you've enhanced it with your performance here", McDonough continued.
Last Wednesday, Gruden appeared on "Golic and Wingo" to talk about his future.to answer the obvious question: Is he going to be the Raiders' next coach?