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Trading Khalil Mack Is an Insane Move for Jon Gruden and the Raiders

The Raiders’ new head coach determined that the roster wasn’t good enough to win now, so his first move was to ... trade away the team’s best defensive player?

It’s a good thing the Raiders signed their head coach to a 10-year contract, because they’re going to need about that amount of time to find another player 50% as good as the one the franchise traded on Saturday morning.

Dealing Khalil Mack to the Bears for a pair of first-round picks before the sun came up in Oakland signals Jon Gruden’s unequivocal takeover of the team’s front office. He emerged from a 10-year coaching hiatus this offseason, scanned the Raiders’ roster and unapologetically decided the depth chart was not good enough to win as presently constructed. The solution? Ship off the franchise’s best defensive player since Charles Woodson for a pair of first-round picks—the kind of players Gruden has not extensively dealt with under the time constraints of a new collective bargaining agreement. The kinds of young guys that he tends to ignore anyway while hoarding 30-plus year old talent that can more quickly legitimize his garbled offense.

“That’s the way he was in Tampa,” Keyshawn Johnson told me this summer for a story I was working on about Gruden’s complicated relationship with his old players. “He always wanted veteran guys, he never wanted rookies, he never wanted young players. He always wanted veteran guys. Well, you drafted the young dude, teach him how to play if you’re such a great teacher of men.”

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The insanity of this move is hard to fathom. What are the odds that Gruden will select two first-round players who can average 12.5 sacks per season between them like Mack has over the last three years? How about three Pro Bowls in four seasons? How about two first-team All-Pro honors? How about one NFL Defensive Player of the Year award?

What if a Bears team that will now start Mack alongside Roquan Smith, Leonard Floyd, Kyle Fuller and Danny Trevathan on defense this year ends up being pretty good? What if those picks end up being in the 20s or late teens?

The sheer ridiculousness of paying $100 million to a coach who has not won a playoff game since the year the Department of Homeland Security was created and then griping about finances when it comes to paying one of your two faces of the franchise is laughable. Mack could knife open a defense from anywhere on the field and he commanded double teams. The Raiders’ front seven front now consists of three rookies—Tank Carradine, Mario Edwards (whom Gruden is also shopping) and Justin Ellis—and Bruce Irvin, who, when seeing the news on Saturday tweeted “No f------ way.” Franchise QB Derek Carr is also less than pleased about the move.

How quick were we to point out supposed tanking efforts in Cleveland and with the Jets in recent years, but because the man from the Hooters commercial, who, during his ESPN QB show wondered aloud why more people weren’t talking about Christian Hackenberg as a first-round pick said it, we automatically take it for gospel. The remaining years of the franchise in Oakland could be worse than expected.

While this is no slam-dunk for the Bears either, given what the team is giving up, but it’s a good time in the franchise’s timeline to experiment. QB Mitchell Trubisky is affordable for another few seasons under the rookie wage scale, so spending quarterback money on another player who can help the team win now makes sense. Gruden worshippers imagining this as a modern day Herschel Walker trade might need to relax. Barring injury, Mack is going to be an immediate franchise-changing player for the Bears, while Oakland tries to collect enough acorns to legitimize this trade to their fans.

Full-scale rebuilds in the NFL are messy, but there is some type of draw we tend to have to a man who uses a gigantic platform to pound the table and say “I alone can fix it.” Gruden-ites might be caught in the hysteria now, but something tells me Reggie McKenzie, the person who won the 2017 executive of the year award for a 12–4 season buoyed largely by a series of excellent drafts including the one that yielded Mack, was doing just fine on his own.