While the Las Vegas Raiders are embarking upon a promising era with a new regime, there are years of mistakes still left to undo. This goes back to the unfulfilled fanfare of Jon Gruden's second tenure as head coach and a roster that has not been filled with savvy draft picks.
Through that whole first offseason when Gruden was back with the Raiders, there was a stubborn refusal to give star pass rusher Khalil Mack the type of contract he had earned. He was eventually traded to the Chicago Bears just before the 2018 season started in a deal that included multiple draft picks going each way.
Mack continued to be a prolific pass rusher for the Bears, and in more recent years, he has given the Raiders an up-close look at how good he still is while playing for the division-rival Los Angeles Chargers.
Raiders' trade of Khalil Mack could have been a lot worse
Getting down to it, trading Mack was more about what the Raiders did with the draft capital they got than the actual move itself. Kristopher Knox of Bleacher Report noted that as he tabbed the Mack deal the worst trade the Raiders have made over the last 10 years.
"Mack was coming off of his third straight Pro Bowl campaign, and the 2016 Defensive Player of the Year was holding out for a new contract. Before the start of the 2018 season, the Raiders sent him to Chicago, along with a 2020 second-round pick and a conditional 2020 fifth-round pick," Knox wrote. "In return, they got a 2019 first-round pick, a 2020 first-round pick, a 2019 sixth-round pick and a 2020 third-round pick. The problem with this trade was that A) the Raiders parted with a Hall of Fame-caliber talent at a premium position and B) they weren't good at maximizing draft capital."
The two first-round picks the Raiders got for Mack yielded running back Josh Jacobs and cornerback Damon Arnette. The 2019 sixth-round pick was ultimately traded, and the 2020 third-round pick gave them wide receiver Bryan Edwards.
With three 1,000-yard campaigns in five seasons, including a rushing title in 2022, Jacobs would go down as a big win for the Raiders from the Mack trade, but he is no longer with the Silver and Black. Edwards wasn't overly productive, but he did average 17 yards per catch over two seasons with the team, and Arnette was, of course, a massive bust.
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Elsewhere on Knox's worst trades list from the last 10 years, however, the Raiders look better. They were able to fleece the Arizona Cardinals when they wanted to trade up to take quarterback Josh Rosen in the 2018 NFL Draft, acquiring third and fifth-round picks in the process.
The Dallas Cowboys traded wide receiver Amari Cooper to the Cleveland Browns for a fifth-round pick and a swap of sixth-round picks in 2022. After surrendering a first-round pick to the Raiders for him in 2018, that was quite a value erosion and it was further highlighted by Cooper posting two 1,100-plus yard seasons for the Browns after leaving Dallas.
The Mack trade was obviously not great for the Raiders. But, they did get one good player out of it for multiple years, and it could have been worse when taking into account the bad trades that other teams have recently made.