Khalil Mack has never been shy about how the Raiders’ breakup went down, and now he’s putting the pieces in plain view.
The trade that sent one of the NFL’s most feared pass rushers to the Chicago Bears on September 1, 2018 has been picked apart for years, with plenty of the blame landing on Jon Gruden after the Raiders brought him back as head coach in 2018 on a 10-year, $100 million deal. But Mack says the story was bigger than one man. During a recent appearance on “ Bussin’ With The Boys. “, he explained that the move grew out of both Jack Del Rio’s exit and Gruden’s arrival.
“It was a mix of Jack Del Rio leaving and Jon Gruden coming in,” Mack said.
Mack also made it clear he never tried to get close to Gruden during that stretch. As he told Taylor Lewan, his agent advised him to keep his distance.
“My agent let me know, ‘You might need to avoid all contact,'” Mack said. “If you talk to him, he’ll probably convince you to do something you’ll regret doing.”
The contract side of the story was already part of the picture. Oakland wasn’t willing to hand the 2016 Defensive Player of the Year the extension he wanted, and that stalled the relationship even further.
Mack has also pointed to the roster around him as a major factor. In 2024, in an interview with Chris Long, he said the Raiders simply didn’t have enough around him on that side of the ball.
“At the time, I feel like we didn’t have much on defense,” Mack said. “I feel like everyone on offense was getting paid.”
That contrast matters. Derek Carr signed a five-year, $125 million contract in 2017, and Gabe Jackson landed a five-year, $55 million deal that same year. Mack, even as the face of the franchise, didn’t get that same easy path to a new contract.
What followed was a huge loss for the Raiders, and the damage didn’t stop with Mack leaving. The draft picks the team got back in the deal never delivered much either, which only made the whole thing sting more as the years passed.
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