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The Legacy of the Khalil Mack Trade Still Lingers Over Jon Gruden

When the Raiders traded Mack to the Bears in 2018, it illuminated Gruden’s dubious scouting and front office decision-making. Those things haven’t necessarily improved, even if Las Vegas is off to a promising start in 2021.

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Khalil Mack and the Bears will visit the Raiders in Sin City on Sunday. It’s fitting. The original sin of Jon Gruden’s Raiders tenure was trading Mack to Chicago in 2018, just before Gruden’s first season began. While Mack vs. Gruden doesn’t register on the reunion Richter scale quite like Tom Brady vs. Bill Belichick, it’s still a Shakespearean matchup. Gruden said he cried for three days after trading Mack. It’s easy to see why he was emotional. At the time of the deal, Mack was only a couple of years removed from winning Defensive Player of the Year honors. Unsurprisingly, the Raiders struggled to replace him. What was surprising was how thirsty they were to get Mack back. Before free agency this year—and yes, I said this year, in 2021—the Raiders called the Bears about reacquiring Mack, according to Vic Tafur of The Athletic. That is the football equivalent of a “u up?” text to your ex.

Ironically, though, the Raiders haven’t needed Mack this season. The team is 3-1 in large part because it’s discovered a nasty pass rush for the first time since the trade. But now there’s concern the Raiders’ 3-0 start was misleading after they were decisively whupped by the division rival Chargers on Monday Night Football this week. After the game, Chargers defensive end Joey Bosa said Raiders quarterback Derek Carr was easily rattled. “We knew once we hit him a few times, he really gets shook,” Bosa told reporters. “And you saw on [defensive tackle Christian Covington’s] sack. [Carr] was pretty much curling into a ball before we even got back there. Great dude, great player. … But we know once you get pressure on him, he kind of shuts down.”

So not only did the Raiders lose to a division rival on national television, but a member of that division rival is now calling their quarterback soft. The Raiders’ response could define their season. Vegas’s next game is a pivot point for its season, and this season is the pivot point for Gruden’s Raiders tenure. Gruden signed a 10-year, $100 million contract to take over a team that had been to the playoffs once since 2003. But in his first three full seasons, Gruden has not produced a winning record. The aftereffects of the Mack trade have been a referendum on Gruden’s decision-making. This season’s promising start is a vindication of sorts, but only to an extent. To find salvation, Gruden has to come face to face with his sins.


Gruden says Mack was one of the reasons he agreed to take the Raiders job in 2018 (he also had 100 million other reasons). But they only spoke on the phone once before their relationship unraveled. Mack wanted a new contract and was mad that the Raiders had spent their cap space before giving him one. The Raiders claimed they didn’t have the cap flexibility to pay Mack what he wanted. Mack contemplated sitting out the entire season, according to Raiders owner Mark Davis, and the Bears pounced like a Fat Bear Week contender. Chicago traded for Mack while also signing him to a contract extension, making him the richest defender in the NFL. The exact terms of the deal were the following:

Chicago Received:

  • Khalil Mack (duh)
  • 2019 second-rounder (pick no. 43, which became TE Cole Kmet)
  • 2020 seventh-rounder (whatevs)

Las Vegas Received:

  • 2019 first-rounder (no. 24, became RB Josh Jacobs)
  • 2020 first-rounder (no. 19, became CB Damon Arnette)
  • 2020 third-rounder (no. 81, which became WR Bryan Edwards)
  • 2019 sixth-round pick (traded, super whatevs)

The immediate returns of the trade could not have been more disastrous for the Raiders. They finished with just 13 sacks in 2018, the second fewest in league history in more than 30 years—Mack had 12.5 for Chicago. Mack single-handedly transformed the Bears defense into the league’s fiercest, and Chicago won the NFC North for the first time in eight years. He was named a first-team All-Pro and was recently named to the 2010s all-decade team. And the Raiders didn’t do much with the picks they received.

The Raiders used one of their first-rounders on Alabama running back Josh Jacobs in 2019. Drafting running backs in the first round is a mistake, but most teams who do so are chasing a three-down back who can contribute as a runner and a receiver, like Saquon Barkley, Christian McCaffrey, or Najee Harris. The Raiders haven’t used Jacobs much in the passing game and don’t seem to trust him in passing situations (the team admitted as much when it signed Kenyan Drake to a whopping $11 million guaranteed over two years this offseason—almost as much guaranteed money as Jacobs got in his entire four-year rookie contract).

In 2020, the Raiders spent the other first-rounder from the Mack trade on cornerback Damon Arnette. It felt like a reach at the time, and Arnette has done nothing to dispel that notion since. In his rookie season, Arnette ranked 130th in PFF coverage grade out of 137 cornerbacks (minimum 20 percent of snaps). Admittedly, last year was a difficult season to be a rookie. But Arnette is such a poor fit in new defensive coordinator Gus Bradley’s scheme that he isn’t even starting this season.

Edwards, the third-rounder from the Mack trade, is a receiver whom Gruden once compared to Terrell Owens (physically, not skills-wise). But Edwards has little to show for the hype. He has more receiving yards in overtime this season (109) than in regulation (105). Some could call that clutch. Realistically, it’s just disappointing. The problem is he isn’t getting open. NFL’s Next Gen Stats measure how much separation a receiver creates from defensive backs. Through four weeks, Edwards ranks dead last among all qualifying receivers.

A running back who doesn’t catch, a receiver who doesn’t get open, and a cornerback who doesn’t play is a light return for a top defensive player in football. But solely looking at the draft picks acquired is an incomplete way to judge the Mack trade. After all, the Raiders traded Mack because his contract demands would hurt the Raiders’ salary cap. As Gruden himself said in 2019: “If we came up with the money to make the [Khalil Mack] contract happen, we wouldn’t have Trent Brown, we wouldn’t have Antonio Brown, Lamarcus Joyner, and Vontaze Burfict, we wouldn’t have Tyrell Williams.”

All five of those players are essential pieces to Vegas’s 3-1 start. Just kidding! None of them are on the team anymore. In fact, those free agents are an all-time burnout class:

  • The Raiders signed offensive tackle Trent Brown away from the Patriots in 2019, but bailed on him after just two seasons and traded him back to New England for a fifth- and a seventh-round pick. The Raiders paid him $36 million for just 16 games.
  • Joyner was the single-worst defender in slot coverage in the NFL during his two years in Oakland, according to Pro Football Focus. The Raiders ended up cutting him, but not before they paid him $27 million for 28 games.
  • The Raiders paid receiver Tyrell Williams $21 million for 42 catches across 14 games. That is $500,000 a catch, or $1.5 million per game, depending on how you want to count. (For context, Tom Brady is guaranteed roughly $1.5 million per game.)
  • Burfict, infamously one of the NFL’s dirtiest players of the last decade, was given a chance by the Raiders when most teams wouldn’t touch him. He made it just four games until he was suspended for the rest of the season for a(nother) helmet-to-helmet hit.
  • Antonio Brown’s tenure with the Raiders was a clown show. The Raiders reportedly designed their entire playbook around him, only for Brown to refuse to show up to practice or wear a league-regulated helmet. He freezer-burned his feet in a cryotherapy cold tub. The Raiders cut him before he ever played for them.


The Raiders paid those players roughly $85 million for just 62 combined games, and their services ranged from unremarkable to unplayable to unemployable. Perhaps the real legacy of the Mack trade is how clearly it illuminates Gruden’s dubious scouting and front office decision-making. There are plenty more examples.

  • The Raiders traded Amari Cooper for a first-round pick from Dallas and spent that pick on Johnathan Abram, a hard-hitting safety who stuffs the run but is unnatural in pass coverage—the opposite of what teams seek in the first round these days.
  • The Raiders took Clemson defensive end Clelin Ferrell no. 4 in 2019, which was a stunning pick even at the time. The Raiders’ plan was reportedly to trade down to take Ferrell, but they couldn’t find a suitor, so they took him anyway. Ferrell has managed just 6.5 sacks in three seasons and was a healthy scratch in Week 1 of this season. The no. 4 pick from two years ago barely plays!
  • P.J. Hall, the Raiders’ second-rounder in 2018, managed just 1.5 sacks in his first two seasons and was cut. He’s not even on a practice squad at the moment, making him the highest-drafted player in 2018 to not be with an NFL team.
  • The Raiders drafted receiver Lynn Bowden Jr. with a third-round pick in 2020, then traded him to Miami for a fourth-rounder the week before the season (the Raiders also had to throw in a sixth-round pick to get the deal done). Cutting bait on a third-rounder before their first season rarely happens. The Athletic reported “some at the team facility thought the rookie was more concerned with picking up new cars than the playbook.” (Bowden bought his mother a car after he signed his rookie contract.) If the Raiders had that big of an issue with Bowden’s study habits, the team should have done more homework before drafting him.

If the Raiders’ draft process is broken, their other personnel decisions have been just as questionable. Perhaps the most illustrative example of the entire Gruden experience was safety Karl Joseph. The Raiders signed Joseph this offseason to a one-year deal guaranteed for $1 million. The team cut Joseph just before the season, but were still on the hook for the money. That happens—sometimes teams are wrong about a player. But this was Joseph’s second stint with the team. Gruden inherited Joseph, who was drafted by the previous Raiders regime in the first round in 2016. Gruden saw Joseph play for a year, let him leave in free agency, signed him to come back, then changed his mind again (and paid for it). It’s a small but representative example of the most basic criticism of Gruden: He gets bored of his players easily, and covets other teams’ players (that’s a sin too, last time I checked).

With all of this mishegas—a coach-GM who isn’t a good GM overseeing a team in the most competitive division in football—the Raiders are an easy flame-out candidate. Yet a month into the season, the Raiders are 3-1 and look feisty. Twice, they’ve overcome a 14-point deficit for a win. Derek Carr leads the NFL in passing yards (1,399) and is finally throwing deep with the confidence fans and critics have been clamoring for. Despite Gruden’s poor personnel judgment, his coaching acumen is working. For now.


And while Gruden is a bad GM, his offensive scheme has been excellent this season. He’s scheming up mismatches, putting speedster Henry Ruggs III in consistently open spots downfield, and putting his receivers in positions to succeed.

But the real improvement has been the defense. For the first time since Mack left, the Raiders have a pass rush. The star of the show has been Maxx Crosby, an uber-athletic pass rusher who is tied with Myles Garrett for the second-most quarterback hits this season (13). Crosby turned his life and career around when he entered rehab for alcohol addiction on March 11, 2020. This season Crosby has been a revelation, registering as PFF’s highest-graded edge rusher through four weeks (one spot ahead of Joey Bosa, the guy who called Carr soft).

Nate Hobbs, a fifth-round rookie cornerback, is tied for sixth among PFF’s cornerbacks, one spot behind Jalen Ramsey. But he isn’t even the no. 1 cornerback for the Raiders on that list—that honor belongs to Casey Hayward, the former Chargers cornerback who followed defensive coordinator Gus Bradley to the Raiders. In Bradley’s system, the Raiders are playing faster, smarter, and more decisively.

PFF grades are not ordained by God. Hayward is not the best cornerback in the NFL, nor is Hobbs on par with Ramsey. But ask Raiders fans about the last time their team fielded an above-average defense, and they might start talking about the 2002 team that lost to Gruden’s Buccaneers in the Super Bowl (that was the last time the Raiders had an above-average defense by points allowed). It may be early to look at Football Outsiders’ efficiency stats, but the Raiders defense ranks no. 15 in efficiency allowed, which would be their highest ranking in more than a decade—even better than any of their defenses with Mack.

Having said all that, we have to pump the brakes a bit on how great this Raiders season has been. The Chargers exposed many of this team’s flaws. Las Vegas has repeatedly started slowly in the first quarter and fallen behind. They’re in the top five in penalties. And the offensive line is a disaster.

Gruden dismantled his offensive line this offseason, trading away the entire right side: Veteran center Rodney Hudson was sent to Arizona, right guard Gabe Jackson to Seattle, and right tackle Trent Brown was sent to New England. They also relied on 38-year-old Richie Incognito to stay healthy, which he could not do (he’s on injured reserve and has not played this season). Functionally, the only Raiders returning lineman was left tackle Kolton Miller.

The players who’ve replaced the other four are doing horribly. By looking at the first four weeks of Pro Football Focus grading (which, again, is not the word of God, but it’s the best measurement we have), Raiders center Andre James has been the worst starting center in the league, and right tackle Alex Leatherwood is the worst starting tackle in the league (the team is having him practice in at least three positions, which can’t be helping him learn one spot correctly). Unsurprisingly, the Raiders have the worst run-blocking grades in the league by PFF, right above the Houston Texans. And that’s not a good recipe for a team whose starting quarterback has been accused of literally folding under pressure.

Now that line is going to have to block Mack and Chicago. The Bears lead the NFL with 15 sacks. Surely the Bears are going to try to rattle Carr early and see how he responds. Carr needs to set a tone of toughness in this game—it is naive to think otherwise—and that will likely mean bouncing back from multiple hits from his old friend. But while this is a big game for Carr, it’s also a huge game for the Raiders defense. The Bears’ left-tackle situation could turn Crosby into an excellent Mack impersonator. Bears QB Justin Fields holds the ball for a long time in the pocket, hoping to make big plays. The time is ripe for the Raiders’ pass rush to make their presence felt in this game. The Raiders are only a few big defensive plays away from a win on Sunday that could propel them to 4-1—which would be just the second time they’ve done that since 2002. The Mack trade was a sin. But if the Raiders defense outshines Mack in a win on Sunday, all will be forgiven.