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Jon Gruden Slams Micah Parson When Talking Comparison to Khalil Mack Trade

Originally posted on Athlon Sports | By Austin C. Boyd | Last updated Sep 2, 2025 7:42 PM ET

As soon as Micah Parsons was traded to the Green Bay Packers from the Dallas Cowboys, many drew comparisons to the deal that saw the Raiders trade Khalil Mack to the Chicago Bears in 2018. That deal also happened right before the start of the regular season.

The man at the center of the Mack trade was former head coach Jon Gruden. It was his first year back on the sidelines with the Raiders, and he wasn't keen on giving the star pass rusher the kind of money that he wanted.

He was asked to discuss the Mack trade and how it related to Parsons' holdout before getting dealt. He gave more insight into what happened with the Raiders.

"I went through this," Gruden said on "The Ronde Barber Show." "When I went back to coach the Raiders, Khalil Mack was on the team. And he would not return not one of my calls. And I kind of laugh about it now, but he never wanted to play for us unless we gave him $100 million or whatever it was the agent wanted, which was the highest contract in the history of defense. We didn't have that kind of money at that time. And we waited it out and waited it out and waited it out."

“He never wanted to play for us unless we gave him $100 million, whatever it was, which was the highest contract in the history of defense.”@BarstoolGruden on the @rondebarber pod talking about the similarities between the @FiftyDeuce @MicahhParsons11 mega-trades. pic.twitter.com/l2DmKtpqhu
— HouseRules (@houserules789) September 2, 2025

Gruden Slams Parsons

To no one's surprise, Gruden seems to be on the side of the Cowboys in this situation. It's a difficult situation to balance, but the Raiders turned the Mack draft picks into Josh Jacobs, Damon Arnette and Bryan Edwards. None of those players is on the team anymore.

Even though many thought the Cowboys lost the trade with the Packers the same way the Raiders did with the Bears, Gruden wasn't a fan of how Parsons was handling the situation toward the end.

"I just watched Parsons in that preseason game against the Falcons. I didn't like that at all," Gruden said. "I mean, not even wearing his uniform, laying on the bench, that is a toxic look."

This article first appeared on Athlon Sports and was syndicated with permission.

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