The Khalil Mack trade was a landmark moment not just in Chicago Bears history, but NFL history. It was the latest and perhaps biggest sign that the league had changed. Teams were far more open to dealing superstar players in the name of obtaining large amounts of draft capital and saving money. This despite a highly inconsistent history of such moves paying off.

See the blockbuster deals for Herschel Walker and Eric Dickerson for examples. One team built a dynasty in the 1990s. The other squandered their currency and became a laughing stock a few years later. There are no guarantees when it comes to the draft. Meanwhile, the player himself never stops being the stud he was before everything went down.

This story is less about the realities of the risk and more about how the Mack trade never should’ve happened. Yet through a series of improbable events, bold decisions, and perfect timing, one of the greatest pass rushers of an entire generation ended up in a city that would understand his value.

Then turn him loose upon the league like never before.

Khalil Mack trade seemed like such a laughable fantasy

Oakland trailed in the game 10-0. The offense had punted yet again. The Dallas Cowboys were poised to add to their lead. The Raiders defense desperately needed somebody to make a play. On second down with just under seven minutes in the first half, Dak Prescott took the snap from the shotgun. He calmly examined the field, confident pressure wouldn’t arrive too quickly.

He was mistaken. No sooner had he hit his back step than a black #52 enveloped him from the back side. Prescott paused for a moment, a bit shocked he’d been dropped from that direction. After all, that was where All-Pro Dallas left tackle Tyron Smith was. He never allowed pressure like that. It had been the case almost all of Prescott’s career.

Mack was different though. Replays showed the Raiders defensive end literally drove Smith into the back of the Cowboys QB with one powerful bull rush. An absurd display of his unnatural power. It was the first of two sacks in the game for Mack, pushing his tally to 10.5 for the season. It was clear to everybody that this man was going to get paid handsomely in the offseason.

Jon Gruden arrives

Despite his best efforts, Mack couldn’t solve the Raiders’ other problems. The team finished a disappointing 6-10. This after going 12-4 the year before. Head coach Jack Del Rio had failed to deliver what the franchise was looking for. That was a consistent presence in the playoff hunt. Thus owner Mark Davis decided to make a chance, and this time he wasn’t taking chances.

The last time Oakland had been a perennial contender was back in the early 2000s. One man was the mastermind during that period. His name was Jon Gruden. It just so happened that the former head coach, who’d retired back in 2008 and spent the previous 10 years as an analyst for Monday Night Football, was looking to get back into the coaching ranks.

Davis had a strong memory of the times with Gruden in charge. He’d always felt his father, the late Al Davis had made a big mistake trading him in 2002. That was hammered home when the Raiders were blasted in the Super Bowl that same year by Gruden’s Tampa Bay Buccaneers. They would not make the playoffs again for 12 years.

Davis wasn’t taking chances on another team luring his prize away. He was going to bring Gruden home, come hell or high water. How did he do it? The obvious way: money and power. Gruden not only received a 10-year deal worth $100 million, absurd numbers for an NFL head coach. He also gained total control of the Raiders roster, supplanting GM Reggie McKenzie.

Nobody knew it at the time, but that decision would light the fuse on what was to come.

Chicago Bears draft fails to fix the pass rusher spot

The 2018 draft would become a successful one for the Chicago Bears. A class driven by the three-headed monster of Roquan Smith, James Daniels, and Anthony Miller. All three would be starters by the end of the first month of the season. Fifth round pick Bilal Nichols out of Delaware would soon join the fun with some big plays of his own. Experts were impressed.

However, there was one glaring issue. For all the good moves GM Ryan Pace had made, he’d failed to address the pass rusher position. One must understand the context of the situation. Just two months prior, the Bears had conducted a significant purge of their outside linebacker spot.

Lamarr Houston was allowed to hit free agency. Pernell McPhee and Willie Young were both cuts after disappointing 2017 seasons. Having failed to sign any notable replacements, that left the draft as their best chance to find somebody who could play opposite Leonard Floyd. Three days and seven rounds later, the Bears had not taken a single outside linebacker.

This meant it could end up being Floyd and veteran Sam Acho as the primary starters for the upcoming season. Not ideal.

The holdout begins

Gruden didn’t have much time to settle into his old chair at Raiders HQ. One notable name who was not there to greet him was Mack. The defensive end didn’t waste time making his intentions clear. He would not rejoin the team until they gave him a new contract. Undoubtedly one that made him among the highest-paid defensive players in the NFL.

This was a problem for a number of reasons. Gruden, for all his coaching expertise, was not a negotiator. He’d never done it before. That made the process of engaging talks with Mack more difficult than normal. Then there was another factor. Something that had stuck with the coach since his previous run during the 2000s.

Though he’d won a championship with a defense laden with superstars in Tampa Bay, the huge amount of money that had been invested in that unit had crippled the teams’ ability to sustain success after Gruden’s arrival. They made the playoffs just two more times from 2003 to 2008. A lack of resources was a big reason for that, in his mind.

Thus while others wondered when the Raiders would finally cave to their superstar’s demands, their new head coach was considering the back door.

A spiteful owner fans the flames

Now this would lead most to blame Gruden for what happened next. However, it takes more than one person to kickstart a blockbuster trade. Especially one involved one of the two or three best defenders in professional football. Gruden may have explored the idea, but it could’ve easily been shot down if Davis had stepped in.

When it comes to spending the team’s money, it’s ultimately the call of the owner. By all accounts, the Raiders made an initial effort to bring Mack to the negotiating table. What they perceived to be a “fair” offer according to inside Benjamin Allbright. However, it was rejected by agent Joel Segal.

While the exact details of the offer are not known, it’s clear Segal wasn’t planning to give the Raiders any sort of discount. Something that Davis did not take too well.

Segal has a long reputation of playing hardball in negotiations. This is why he has so many high-profile clients including Andrew Luck and Patrick Peterson among several others. For an organization considered among the least-lucrative in the NFL like Oakland, any sort of attempt to squeeze more money from them would’ve met with resistance.

If it’s true, then an indignant Davis would’ve been far more open to Gruden’s idea of trading the 27-year old pass rusher.

Prying open the door

It was apparently by the summer that Pace knew of the situation at outside linebacker. That was why when the rumors surfaced before training camp that Mack might be available, he called the Raiders about it. At first his inquiries were rebuffed. Clearly Oakland wasn’t ready to abandon hope they could still sign him at the time.

Still, Pace had frequent discussions with new head coach Matt Nagy. Both agreed that the Bears were close to putting something together. They just needed one more big push to put it over the top. The price would be high, but they were convinced it would be worth it.

“It’s very easy in our league to play it safe and play it cautious. And not that we’re going to be reckless, but we’re going to be aggressive.”

Soon the Raiders began to entertain offers. While half the league was involved in talks, there were three teams that emerged as likely landings spots. They were Chicago, San Francisco, and Green Bay. Both the 49ers and Packers had more draft capital at their disposal. Nobody felt the Bears had any sort of edge.

However, they did have one thing.

Public perception won the day for Pace

Hall of Fame quarterback Steve Young had a great quote about the reality of football. It took him several years to become a star in the NFL. For the longest time, his teammates wouldn’t accept him as a leader. Then in 1994, after screaming at his head coach during a loss to Philadelphia, everything changed. It was at that point he learned a vital lesson.

“Perception is reality. If you’re perceived to be something, you might as well be it because that’s the truth in people’s minds.”

Indeed it was a perception that gave Chicago the opening they needed to pull off a stunner. Raiders GM Reggie McKenzie like the offers his team was getting, but the one from the Bears made the most sense to him. Why? The odds favored the draft picks they got back in the trade being on the higher end. This because of how poor the team had been in years past.

Chicago hadn’t had a winning season in four seasons and had gone 5-11 the year before. They had the biggest question marks, especially at quarterback. Green Bay had Aaron Rodgers. San Francisco had Jimmy Garoppolo. There was little belief in Mitch Trubisky at that time. Thus Oakland worked out the compensation.

Raiders get:
  • 1st round pick in 2019
  • 1st round pick in 2020
  • 3rd round pick in 2020
  • 6th round pick in 2019
Bears get:
  • Khalil Mack
  • 2nd round pick in 2020
  • 5th round pick in 2020 (conditional)

Many people were stunned when the trade was announced. Not just because the Raiders had the audacity to deal one of the best players in the game in his prime. They were also shocked at how much Pace managed to get back. Not only did he scored Mack, but an additional two picks in 2020 including a 2nd rounder.

Keep in mind the Bears have enjoyed a lot of success in that round under Pace’s watch. Eddie Goldman, Cody Whitehair, James Daniels, and Anthony Miller were all take in the 2nd. Many felt Oakland could’ve and should’ve gotten more. 49ers GM John Lynch even said months later he feels the offer he made to the Raiders was superior to the one they ultimately got from Pace.

“I don’t want to beat a dead horse, but we tried like heck to acquire Khalil Mack. But it didn’t work out. But, you try by any means necessary to get it but it’s not easy. Guys that are free, they never become free because they’re so coveted in this league. They’re franchise (tagged) typically or they work out a new deal.”

During the interview, Lynch was asked directly if he believed that the 49ers made a better offer than the Bears.

“I continue to (believe that),”

Money well-spent

The Bears didn’t waste any time. Barely a day after the news dropped that Mack was coming to Chicago, they worked out a new contract. He would become the highest-paid defender in the NFL with a deal worth $141 million over six years. That included $60 million in guarantees. It was an absurd amount of money for a non-quarterback, but Pace never flinched.

Still, it was hard to know for certain how quickly Mack could adapt to his new defense. It was on September 1st. He’d missed all of training camp and the preseason. Despite his obvious skill, there was only so much one could expect from him with such a late start. Then on opening night at Lambeau Field in Green Bay, Mack reminded everybody that he doesn’t play by normal rules.

As debuts go, the star pass rusher probably had the best in Bears history. In addition to a sack, Mack also had a forced fumble, a recovered fumble, and an interception return for a touchdown. All of which came in the first half o the game. It was then people realized what the Bears had gotten, and what the Raiders had given up.

Three months later, it was clear the balance of power in the NFC had drastically shifted. Led by Mack, the Bears defense finished 1st in the league in points allowed. They collected 27 interceptions, forced 18 fumbles, and scored six defensive touchdowns. Chicago went 12-4 and made the playoffs for the first time in eight years. Mack had 12.5 sacks, the highest total a Bears pass rusher had achieved since 1993.

The Raiders? As a team they finished with 13.

It was a hell of a first act. Perhaps the craziest part of all is that it may only be the beginning. Mack is squarely in his physical prime and doesn’t even turn 30 until 2021. Great pass rushers tend to last at least until around 33 to 34. Many though have proven they can go all the way to 36 or 37 still producing 10-sack seasons.

The belief around the league is the Bears got themselves a player who will be in the Hall of Fame after he retires. Yet the craziest part of all is that trade may not be done rewarding them. They still have those two draft picks to look forward to next year. If Pace and his front office can turn them into quality players or even another Pro Bowler? This may go down as the best trade in franchise history.