Five years ago today, the Bears made one of the most significant moves in franchise history.

On the morning of September 1, 2018, they added the final piece to their defense with the addition of Khalil Mack. It felt like a fever dream.

The move was the cherry on top of an incredible offseason, and it really felt like the Bears were going places. They spent more money than anyone and appeared to do it well.


Despite going 5-11 the year before, there was hope Mitch Trubisky would make a leap in his second season, and the front office made a concerted effort to build around him. They completely revamped the receiving core, adding four starting pass-catchers through free agency (Allen Robinson, Taylor Gabriel, and Trey Burton) and the Draft (Anthony Miller). They also added a top-10 pick to the linebacker room in Roquan Smith. Most importantly, they even seemed to fix their kicking woes by signing Cody Parkey, who only missed two kicks for Miami the year prior, to a multi-year deal in the offseason. While questions remained about how the team would gel after such a massive roster turnover, they were suddenly full of talent across the board, and Mack was the final addition that indicated they felt they were ready to compete.

The idea of adding Khalil Mack was absurd before the deal, as he was coming off three straight Pro Bowl seasons and was legitimately one of the league’s premier players.

However, the pass-rusher became the subject of trade speculation when he did not see eye-to-eye with new Raiders head coach Jon Gruden on a contract extension. Still, no one expected them to move on from the 27-year-old until the deal was announced that Saturday morning.

In return, the Raiders received two first-round picks, a third-round pick, and a sixth-round selection for Mack, a second-round pick, and a seventh-round selection. The Bears promptly made Mack the highest-paid defender in NFL history, signing him to a six-year, $141 million deal seemingly before his plane landed at O’Hare.

Was it a haul? Sure. With that said, everyone agreed: The Bears’ brass pulled off a highway robbery. Ryan Pace took advantage of an over-emotional Jon Gruden and fleeced the Raiders out of their best player. They landed one of the league’s best pass-rushers in the prime of his career. They added one of the NFL’s best players and actually managed to get a high-round pick back from the Raiders to go along with him. The move left one fanbase heartbroken, three others terrified, and the remaining 27 others jealous.


Now that we covered just how massive of a move it was at the time, how does it hold up five years later?


For starters, Mack’s tenure in Chicago could not have gotten off to a much better start. He provided an immediate jolt to the Bears’ defense and had one of the most electrifying opening-week performances in recent memory. Despite joining the team only eight days before their season opener, he had a strip sack and a pick-six against the rival Packers in their Sunday night matchup. Mack also helped the team grab a 17-0 halftime lead over their rival. Naturally, his performance was not enough to spare the loyal fanbase from heartbreak, as they still lost the game 24-23. However, the seed for a promising season got planted that night, even if it was tough for Bears fans to see through tear-filled eyes.

Mack continued to play at an extremely high level throughout the remainder of the 2018 season, as he spearheaded a defensive attack that led the league with 36 takeaways. He was also a huge reason the team finished with a 12-4 record, clinching the NFC’s third seed. The edge-rusher proved he was worth every penny the Bears spent on him, as he recorded 12.5 sacks despite missing two games (the first two missed games of his career) during the season. However, much like the opener against Green Bay, the season would end in heartbreaking fashion, losing to the sixth-seeded Eagles in the Wild Card round following a missed field goal attempt by the kicker they broke the bank on in the offseason.

Unfortunately, the ‘Double Doink’ seemed to leave a dark cloud hanging over the Bears throughout the rest of the Matt Nagy era. The curse was so strong that even Mack, one of the best players of this generation at his peak, was not spared from it. Ironically, Ryan Pace was still named the Executive of the Year by Sporting News for his work in the 2018 offseason, which says a lot about how impactful the Mack trade was.

As easy as it is to blame Cody Parkey for everything that’s wrong with the world, his untimely blunder was not the only factor that led the Bears (and Mack) to fall off in the years that followed. Trubisky also took a step back in each of the next two seasons, indicating that his 2018 campaign was nothing more than a mirage. Would they have still made the move without the belief that Trubisky was the guy? Maybe. Ryan Pace always seemed to do things differently. However, it would have been ill-advised to make such a trade without the hope that you found your franchise QB.

Mack was unfortunately also plagued by nagging injuries throughout his time in Chicago. He managed to play through the pain throughout 2019 and 2020, but there were a few weeks where he was a full participant in practice throughout the week. The edge rusher was still productive, leading the team in sacks each year with 8.5 and 9, respectively. However, he was seemingly never at full strength, which was obvious on gameday—his 2021 season spanned only seven games before he suffered a season-ending foot injury.

The hiring of general manager Ryan Poles last offseason marked the end of Mack’s tenure in Chicago, as he traded the star pass-rusher to the Chargers in his first major move as GM. The Bears were coming off a disappointing 6-11 season, and Poles knew he would have to tear down the fort to build a championship-level squad. Getting Mack’s hefty contract off the books was pivotal for the team to accomplish that, even if it meant shipping away the defense’s best player. Most first-year general managers wouldn’t have had the guts to pull off the move, but the new man at the helm viewed it as a necessary evil.


The Bears trade for Khalil Mack should have been celebrated for years to come. It was a great move that completely turned the Bears defense around. 2018 was incredible, but it should have been the start of something memorable instead of an asterisk.

However, other factors came into play, and they were not nearly as competitive as they should have been during Mack’s time in the Windy City.


Five years later, imagining what could have been feels more appropriate than reminiscing on what was.

Photo: Chris Unger/Getty Images

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