Jon Gruden reportedly tried to bring Khalil Mack back to Raiders

One of the first major moves Jon Gruden made after he was named the head coach of the Raiders in 2018 was trading Khalil Mack. The decision was not popular, and Gruden reportedly tried to reverse it this offseason.

The Raiders reached out to the Chicago Bears about a potential Mack trade prior to free agency in March, Vic Tafur of The Athletic reports. The Bears had salary cap issues at the time, but they still had no interest in moving on from Mack. They ended up cutting All-Pro cornerback Kyle Fuller and restructuring some other contracts instead.

Once Chicago shot down the Raiders’ request, Las Vegas then pivoted to free agency and signed Yannick Ngakoue to a two-year, $26 million deal.

Gruden traded Mack to the Bears for a massive haul that included two first-round draft picks. The decision came after Mack held out of the preseason in 2018 because he wanted a new contract. Gruden said he was extremely distraught over the trade but has gotten snippy at times while defending his thought process.

Mack has made it clear that he is bitter about the way things ended for him with the Raiders. He has posted 30 sacks in three seasons with the Bears, while the Raiders have struggled to pressure opposing quarterbacks. It’s fair to wonder if Gruden regrets the trade.