Jon Gruden reportedly tried to get Khalil Mack back on Raiders, but Bears weren't interested

·3-min read

Remember after the 2017 season, when the Las Vegas Raiders (at the time still in Oakland) hired Jon Gruden? And then he started putting his stamp on the Raiders in ways that didn't always make sense?

You'll never believe this, but Gruden may feel some regret about one of those moves. 

OK, so you will probably believe it. Especially since it concerns outside linebacker Khalil Mack, who was involved in one of the most memorable moves of Gruden's first season with the Raiders.

Gruden trades Khalil Mack away

This all began when Gruden traded Mack to the Chicago Bears just over a week before the 2018 season got underway. In return, the Raiders got a bundle of draft picks.

The move was seen as pretty questionable at the time, and not just because the Raiders were short on Mack-like talent. Mack didn't want to play on the fifth-year option of his rookie contract, and had been holding out for an extension instead. The Raiders made him an offer that Gruden admitted was far less than what Mack eventually signed for: a six-year, $141 million contract extension that the Bears offered him shortly after trading for him. 

Gruden said he "cried for three days" after making that trade, so it's not entirely surprising that he might want to try and get Mack back on the Raiders at some point, right? Turns out he reportedly tried to do exactly that. 

CHICAGO, IL - DECEMBER 13: Chicago Bears outside linebacker Khalil Mack (52) looks on in action during a game between the Chicago Bears and the Houston Texans on December 13, 2020, at Soldier Field in Chicago, IL. (Photo by Robin Alam/Icon Sportswire via Getty Images)
The Raiders reportedly tried to trade for Khalil Mack, three years after trading him away. (Photo by Robin Alam/Icon Sportswire via Getty Images)

Gruden tries to get Mack back

Let's jump forward in time to March 2021, just before free agency kicked off. The Raiders had needed pass-rush help ever since they traded Mack away in 2018, and what better player to fill that gaping void than Mack himself, right?

According to The Athletic's Vic Tafur, Gruden called up the Bears in March to see if they'd be interested in sending Mack back to the Raiders for an unknown return. It's a move that has regret wafting off it it like cartoon stink waves, and you can almost imagine the person who took that call at Bears HQ putting their hand over the phone and telling their coworkers "you'll never believe what Gruden just asked me." 

It wasn't totally outlandish though. Tafur pointed out that the Bears were having pretty major cap problems this offseason, and it was worth a shot to see if they'd be willing to solve that by unloading Mack and his large contract. But on the other hand, they just drafted an incredibly promising quarterback and are trying to build something solid. Cap problems or not, trading Mack back to the Raiders (or anywhere) isn't how you do that. 

According to Tafur, the Bears told Gruden they weren't interested, and they ended up resolving their cap issues in other ways. The Raiders decided to sign Yannick Ngakoue to solve their problem. At this point, if Gruden is interested in truly fixing the problem he created when he traded Mack three years ago, he's probably going to need a time machine to do it. 

More from Yahoo Sports:

Our goal is to create a safe and engaging place for users to connect over interests and passions. In order to improve our community experience, we are temporarily suspending article commenting