Khalil Mack Shares what Agent Told Him about Jon Gruden Prior to Raiders Trading Him in 2018

On September 1 it will be eight years since the Raiders traded Khalil Mack (and a second-round pick) to the Chicago Bears for two first-round picks.

The trade is still regarding as one of the worst personnel decisions of the second Jon Gruden era with the Raiders, and last week on Bussin’ with the Boys, Mack shared a few more details around his final days in Silver & Black.

“It was a mix of Jack Del Rio leaving and Jon Gruden coming in,” Mack said of his departure from the Raiders.

“My agent let me know, like, ‘Hey, Jon’s very good with his words so you might need to avoid all contact.’ He’s like, ‘Because I know you love football and if you talk to him and he’ll convince you to do something you probably will regret doing.”

“It’s just the fact that I love football… and I love to be around my guys. And going through that process and not being there for OTAs and missing out on training camp… that whole process of not being with my guys, it was tough. I feel like that was the hardest part of that process. Not being with your guys, with Derek Carr and my dudes, Bruce Irvin, Justin Ellis.”

Raiders wasted 2 of their 3 picks from the Bears

There’s no question the Bears ended up “winning” the Mack trade, and that was probably true before the draft picks were made.

The fact that the Bears got any picks from the Raiders for Mack is still ridiculous, but to get a second-round pick along with Mack was one of the slickest maneuvers of Ryan Pace’s tenure as GM in Chicago.

With the three picks they received from Chicago, the Raiders drafted Josh Jacobs, Damon Arnette, and Bryan Edwards.

Jacobs ended up being an NFL rushing champ, but Arnette and Edwards only played a combined 28 games with the Raiders.

What could have been…

It’s water under the bridge now, but the Mack trade still sticks in the crawl of many Raider fans.

From a defensive standpoint, the organization never truly recovered from the Mack trade. The Raiders have finished 24th or worse in scoring defense in all but one of the last eight seasons.

Maxx Crosby has been an elite edge rusher for the Raiders in his seven NFL seasons, but Raider fans can only imagine what the defense would have looked like with Crosby lined up across from Mack for the last seven years.

x: @raidersbeat

Khalil Mack’s Agent Told Him To Avoid Jon Gruden + What Went Wrong With Chicago Bears | Bussin’

Future Hall of Famer Khalil Mack reveals the untold story of his agent warning him to avoid all contact with former Las Vegas Raiders coach Jon Gruden because he’d “convince you to do something you’d regret.”