Why NFL exec would rather be Raiders than Bears post-Khalil Mack trade

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When the Raiders traded Khalil Mack to the Chicago Bears prior to the start of last season, Jon Gruden received a heavy dose of criticism from fans and media alike. 

After all, why would trade one of the most dominant defensive players in the NFL? That never happens. 

Making matters worse, Mack helped lead the Bears to an NFC North title and the playoffs in 2018, meaning the 2019 first-round pick the Raiders got for Mack came late in the first round at No. 24.

Gruden restocked the Raiders' roster, filling it with talented rookies that will be key building blocks for the next great era of Raiders football. At least, that's the hope.

The Raiders' rookies -- especially running back Josh Jacobs, who they took with the Mack pick -- have been integral to their 4-4 start and appear primed to set the Raiders up for long-term success. 

Meanwhile, the Bears have floundered this season, losing four in a row to fall to 3-5. Quarterback Mitchell Trubisky has struggled and the Bears don't even have their first-round pick, which also will go to the Raiders. 

So, who actually won the Mack trade? Better yet, which team would you rather be as of Week 9 in 2019?

"Oakland, no doubt about it," one NFL exec told The Athletic's Mike Sando.

“Gruden got so criticized for making that Mack trade,” the exec said. “He got crushed -- his ego and all that. Is the guy (Mack) a great player? Yeah. Should you trade great players? Probably not. But there is no single way to put together a team. It’s important that you have a plan and stick with your plan.”

Gruden had a vision for how he wanted to build the Raiders when he returned. It involved trading Mack and wide receiver Amari Cooper and resetting the course of the franchise. So far, it appears to be working. 

“What I am saying is, Jon Gruden had a plan and his plan wasn’t necessarily Mack,” this exec told The Athletic. “It was for a bigger offensive line, being able to run the ball. He’s won a Super Bowl and he was hired to be the coach. Does he get a chance to put his plan into place? Yeah, he should, and it looks like right now his plan has kind of turned a corner."

[RELATED: Raiders rookie class' dynastic vision ahead of schedule]

The true winner of the Mack trade won't be determined for years. The Bears saw immediate returns, but if they continue to backslide and lose a top-10 pick to the Raiders after already losing out on a talent like Jacobs, the pendulum will swing back in the Silver and Black's favor. 

“Did the Raiders lose the battle (of the Mack trade) but win the war (with their overall plan)?” the exec asked Sando. “The war is not over. We are still fighting battles. I just think we can see the Raiders’ plan coming together a little more.”

After eking out a narrow win over the Lions on Sunday, the Raiders are in the thick of the AFC playoff hunt at 4-4. An easier back half of the schedule could set Gruden's club up to play meaningful football in December and perhaps January. The Bears, on the hand, are dead to rights barring a long winning streak.

Looks like Gruden might get the last laugh after all.

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