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Jon Gruden reportedly passed up on an interesting opportunity in the 2020 NFL offseason that few head coaches around the league would have ever said no to. He apparently rejected a proposal that would have brought Tom Brady to the Las Vegas Raiders as his quarterback.
Less than two years later, Brady had already won another Super Bowl ring, and Gruden was relieved of his duties as the head coach of the Raiders. NFL analyst John Middlekauff discussed the situation on a recent episode of his podcast, "Haberman & Middlekauff."
“I mean, Jon would’ve gotten fired still, it would’ve been a disaster. I don’t think it would’ve worked at all. I think it would’ve been a disaster. The best thing that Mark Davis did was allow Jon Gruden to say no on it.”
Gruden was released after a series of insensitive emails were discovered. Middlekauff could be right. Maybe Brady wouldn't have saved Gruden's job. It would have been interesting to see if they could have won a Super Bowl ring together.
Jon Gruden passes on an opportunity to land Tom Brady
The goal of most head coaches is to win a Super Bowl, and the best way to do that is by having an elite quarterback on your team. There is no better example of this than Tom Brady. He has won seven total Super Bowl rings split between the New England Patriots and Tampa Bay Buccaneers. If a coach has the chance to get Brady, they should probably take it.
Jon Gruden had other ideas. A wild story recently surfaced. Apparently, UFC president Dana White, who is friends with Brady and does most of his business in Las Vegas, worked out a deal. This deal would have brought Tom Brady and Rob Gronkowski to the Raiders, rather than the Buccaneers when they switched teams during the 2020 NFL offseason.
White made this claim during a guest appearance on "UFC with the Gronks." He allegedly had everything worked out with Raiders owner Mark Davis, pending approval from Jon Gruden, who was given some power in roster decisions as part of his contract with the team.
Gruden shockingly rejected the offer, resulting in Brady and Gronkowski ultimately signing with the Buccaneers. Less than two years later, the Buccaneers had already won a Super Bowl ring and Gruden lost his job as the head coach of the Raiders.
