The Khalil Mack trade remains one of the most debated moves in Raiders history. On September 1, 2018, Oakland sent the star pass rusher to the Chicago Bears after failing to reach a long-term contract agreement. Jon Gruden received much of the blame because he had returned as the Raiders’ head coach only months earlier.
Mack has discussed the breakup several times since then, including in 2023 interviews. A new 2026 appearance on Bussin’ With The Boys added another detail: Mack said the situation was a mix of Jack Del Rio leaving and Gruden arriving, while his agent advised him to avoid contact with Gruden. Contract demands, roster-building concerns, and the changing relationship between Mack and the organization all contributed to the split.
Why roster costs influenced the decision
Oakland’s defense struggled in 2017, ranking 23rd in total defense, 26th against the pass, and 20th in points allowed. The Raiders also finished near the bottom of the league in takeaways, giving the organization several defensive needs beyond Mack.
Raiders owner Mark Davis later said the team had numerous roster holes and questioned how Oakland could build a complete team while carrying major contracts for both Derek Carr and Mack. The financial demands of a record-setting Mack extension, therefore, became part of a broader roster-building debate.
Gruden later argued that trading Mack gave Oakland financial and draft flexibility for its 2019 overhaul. He pointed to additions including Trent Brown, Lamarcus Joyner, Vontaze Burfict, Tyrell Williams, and Antonio Brown, although Antonio Brown arrived in a trade rather than as a free-agent signing.
Mack wanted a new deal in 2018
Mack stayed away from the Raiders’ offseason program, mandatory minicamp, training camp, and preseason while seeking a long-term extension. He was scheduled to make $13.846 million under the fifth-year option on his rookie contract.
General manager Reggie McKenzie said Oakland’s goal had been to sign Mack and that the team presented an offer, but the sides remained too far apart financially to reach an agreement. The unresolved contract dispute ultimately ended with Mack being traded to Chicago.
Hours after the trade, Mack agreed to a 6-year, $141 million extension with the Bears. The deal included $90 million guaranteed and $60 million guaranteed at signing, making him the NFL’s highest-paid defensive player at the time.
Derek Carr and Gabe Jackson got paid first
Quarterback Derek Carr signed a 5-year, $125 million extension with Oakland in June 2017. A week later, guard Gabe Jackson agreed to a 5-year, $56 million extension. Jackson’s $11.2 million annual salary ranked third among NFL guards at the time.
Mack later said the situation bothered him because he felt the Raiders had relatively little talent around him on defense, while offensive players were receiving major contracts. His frustration formed part of the broader contract dispute over what he believed his value should be.
The Raiders did attempt to extend Mack before his 2018 holdout. Owner Mark Davis later said Oakland approached Mack’s camp after Carr’s 2017 deal with an offer that would have made Mack the NFL’s highest-paid defensive player, but Mack’s camp chose to wait, and later negotiations failed.
Gruden was only part of the story
Gruden returned as Oakland’s head coach in January 2018, months before the Mack trade. His arrival made him an obvious focus after one of the NFL’s best defensive players was dealt away. Raiders owner Mark Davis later said Gruden wanted Mack to stay and rejected the idea that the coach alone was responsible for the trade.
General manager Reggie McKenzie likewise described the failed contract negotiations as the central issue behind Oakland’s eventual decision to move Mack. Mack’s latest comments add more nuance rather than completely removing Gruden from the story.
In his 2026 Bussin’ With The Boys appearance, Mack said the situation was a mix of Jack Del Rio leaving and Gruden arriving, and he said his agent advised him to avoid contact with Gruden because the coach might persuade him to change course.
Chicago won a competitive trade market
Chicago sent Oakland first-round picks in 2019 and 2020, a 2019 sixth-round pick, and a 2020 third-round pick. The Bears received Mack along with Oakland’s 2020 second-round pick and a conditional 2020 fifth-round pick that ultimately became a seventh-round selection.
McKenzie said trading Mack was not Oakland’s original plan and that more than half of the NFL contacted the Raiders about a potential deal. He said Oakland favored teams it believed could provide earlier draft positions.
Mack later said he believed San Francisco had made an extremely strong proposal that included 2 first-round picks and players. He said he thought the 49ers’ package was technically better but believed Oakland preferred Chicago’s picks because the Raiders expected them to land higher in the draft.
Fun fact: Mack’s 16 career forced fumbles at Buffalo stood as the NCAA FBS record until Buffalo linebacker Red Murdock surpassed it with his 17th career forced fumble in 2025.
Mack has explained his side over time
Mack has discussed the Raiders trade in several interviews rather than breaking his silence only now. In a 2023 appearance on Chris Long’s Green Light podcast, he said he took the situation personally because he felt Oakland lacked defensive talent while offensive players were receiving major contracts.
Long was not Mack’s former teammate. During that same 2023 conversation, Mack said he believed San Francisco had offered 2 first-round picks and players, and he considered the 49ers’ proposal one of the strongest available.
Mack added a different piece of the story in a 2026 Bussin’ With The Boys appearance. He said Jack Del Rio’s departure and Jon Gruden’s arrival both affected the situation, while his agent advised him to avoid direct contact with Gruden during the contract dispute.
The Mack picks produced mixed results
The Raiders did not use a Mack trade pick on Clelin Ferrell. Oakland selected Ferrell at No. 4 overall in the 2019 draft with its own first-round selection. His production never matched his draft position.
The first-round pick acquired directly from Chicago in 2019 became No. 24 overall, which Oakland used on running back Josh Jacobs. The Raiders later used Chicago’s 2020 first-round pick on cornerback Damon Arnette and the 2020 third-round pick on receiver Bryan Edwards. The 2019 6th-round selection from Chicago was later traded to the New York Jets.
Safety Johnathan Abram also did not come from the Mack trade. Oakland selected Abram at No. 27 overall in 2019 with the first-round pick acquired from Dallas in the separate Amari Cooper trade.
What this trade still teaches NFL teams today
The Mack trade illustrates how major contracts can shape roster construction. Teams have to balance star salaries against depth and other needs, and a blockbuster contract can affect spending throughout a roster.
It also shows how communication can affect player relationships. Mack later said he took the situation personally and felt Oakland lacked talent around him on defense, while offensive players were receiving major contracts. Better communication might have changed the course of the dispute, although the outcome cannot be known.
The trade remains a prominent example of the tension between paying an elite player and exchanging that player for draft capital and financial flexibility. Its lessons about timing, valuation, communication, and roster construction still resonate in the NFL.
Little-known fact: Despite his talent, Mack was rated just a two-star recruit coming out of high school.
TL;DR
- Oakland and Mack failed to reach a long-term agreement, while Raiders officials later offered different explanations for the roster and financial considerations surrounding the trade.
- Mack held out during the 2018 offseason and preseason while seeking a long-term extension.
- Derek Carr and Gabe Jackson received major extensions in 2017 before Mack’s contract dispute culminated in 2018.
- Gruden was not the sole cause of Mack’s departure: Raiders officials said they wanted Mack to stay, while Mack said in 2026 that Gruden’s arrival was one part of the situation.
- Chicago’s offer, headlined by 2 first-round picks, was the package Oakland accepted after more than half of the league inquired about Mack.
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This article was made with AI assistance and human editing.
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