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With the news that general manager Reggie McKenzie is out in Oakland now, it seems like the perfect time to revisit Jon Gruden’s big trades this season.

The head coach came crashing in like a bull in a china shop to undo all the hard work McKenzie had done to build Oakland’s roster. In the process, he traded away the team’s best defensive player (and one of the league’s best) in Khalil Mack. Then midway through the season he got rid of its best offensive weapon in Amari Cooper.

Quite aside from the fact that both players have since elevated their respective teams to playoff — and potentially championship — contenders, Gruden’s moves have backfired in an even bigger way.



Remember, when he made those moves, it was thought that perhaps Chicago would be a middling team that would struggle to make the playoffs. And the Cowboys were 3-5, which seemed to indicate the Raiders would land a savory top-5 or top-10 pick out of the exchange.

So, Gruden’s logic was that the Raiders would be landing at least one high first-round pick and another that would be at the worst in the teens.

Since then, both teams have become division leaders and appear to have excellent shots to make a deep playoff run.

Based on current records, Oakland’s first-round pick acquired in the deal with Chicago is now set to be the No. 26 overall pick. The first-round pick acquired in the deal with Dallas is set to be the No. 25 overall pick.



It also stands to reason that Chicago will only get better, given the talent it has on both sides of the ball and due to the continued development of Mitch Trubisky next year. With that logic, both first-round picks landed by Oakland in the deal that sent Mack to Chicago are not worth nearly what Gruden was expecting to land.

That must grate on John Lynch.

The 2018 season has been an abject disaster. Gruden has failed to adapt to the modern NFL, and he’s gotten rid of his best players in the process. He’s brought in a bunch of ineffective older players and now has less to work with in revamping the roster with youth than he was expecting to have when he made the deals to unload Mack and Cooper to begin with.

Buckle up, Raiders fans. It seems like this ride is only going to get bumpier as time goes by. On that note, here’s a handy reminder that the countdown to Gruden’s departure has already begun.


Jesse Reed
Managing Editor at Sportsnaut. Featured on Yardbarker and MSN.com, and formerly was a breaking news writer/NFL analyst for Bleacher Report.