The moment Jon Gruden signed a 10-year, $100 million contract that would mark the return of ‘Chucky’ to the NFL sidelines, it was inevitable there would be fireworks in Oakland. But nobody could have expected what would happen next: Gruden trading Khalil Mack to the Chicago Bears in exchange for a package including two first round picks.
The two first round picks, a 2020 third round pick, and a sixth round selection in 2019 that the Raiders received is the highest compensation given for a defensive player in NFL history. But along with trading a future Hall of Famer, they also gave the Bears a second round pick and a conditional fifth round pick in 2020.
The fact Oakland gave up more than just Mack is unacceptable, as Gruden held all of the leverage with multiple teams highly interested in acquiring the former NFL Defensive Player of the Year.
NFL executives and scouts across the league agree there is no excuse for the timing of the move and the lack of compensation the Raiders received in the trade.
“The entire thing is confusing,” one high-ranking NFL executive told The Athletic’s John Middlekauff. “If you publicly say half the league was interested, how do you include a second? That should be a general manager’s dream. A true seller’s market. The very definition, you should hold an auction.”
On the surface, exchanging a second round selection for a third round pick may not seem like a big deal. But when you factor in how the Raiders will perform without Mack, and that the Bears could very well be in the playoffs, the drop from the second round pick the Bears acquired to the Raiders pick in the third round could be steep.
“Worst case — what if the Bears go 10-6 next year and Raiders go 5-11?” an NFL exec explained. “That pick swap could lead the Bears to having pick 40 and the Raiders having pick 80. That’s insane. The Raiders were giving them Khalil Mack. Why would they have to risk that? They had the leverage.”
“If they were willing to part with two first-rounders, no chance they were blowing the deal over a pick swap,” added another executive.
The most powerful move in a negotiation is to say no. When the Bears asked for a second round pick, Gruden should have told them to kick rocks.
As Bears head coach Matt Nagy told Middlekauff, “we weren’t stopping until we got him.”
Had Gruden waited even just a couple more days to trade Mack, he could have very likely received more in compensation as well as keeping the second and fifth round picks he sent Chicago.
The second glaring issue with Gruden’s handling of the Mack trade is the timing of the move. Back in January when Gruden took over as Raiders head coach, there was no secret that both Aaron Donald and Mack would command over $20 million per year.
After the Bears reached a record six-year, $141 million extension making Mack the highest paid defensive player in NFL history, Gruden made it clear he never intended to pay Mack the salary that the market demanded.
“We made him an offer,” Gruden said. “I don’t believe we were anywhere close to where the Bears were.”
So if Gruden never planned on being close to what the market demanded for Mack, he should have traded him before the 2018 NFL draft when the order was already set.
Among the teams reportedly interested in Mack were the Cleveland Browns, who held the first and fourth overall picks in the draft. With the Browns bounty of picks in the upcoming years, it is highly likely Gruden could have received the fourth overall pick along with a second first round pick in 2019.
With that pick, the Raiders could have drafted Bradley Chubb who was widely-viewed as the top defensive player in the draft. While Mack is irreplaceable, Chubb is still a very talented pass rusher that the Silver & Black could have had immediately and for at least four years under a rookie contract.
Instead, Gruden and the Raiders are left guessing as to where the two first round picks received from the Bears will fall. With a legitimate chance Chicago makes the playoffs, both picks should fall outside of the top-15 decreasing Oakland’s chances of landing a true impact player.
Another option would have been to wait until after the 2018 season to trade Mack, when the order for the 2019 draft would be set. When asked why Gruden decided to deal Mack just one week before the season opener, he responded, “No guarantee we get two 1’s next year.”
Come on. Gruden had multiple teams practically begging for Mack. The only way that would change in the next few months would be a major injury to Mack, which seems highly unlikely.
It is never a good look when a team moves on from a transcendent talent such as Mack. But a deeper dive into the trade paints an even bleaker picture for Raider fans, one that executive and scouts agree shows the Raiders got fleeced.