In 2018, Jon Gruden was mocked by EVERYBODY when he traded away their best defensive player in Khalil Mack for two first-round draft picks and a sixth round pick to the Bears. By the way, the first of the first-round picks for Oakland from Chicago was Josh Jacobs. Jacobs as of this week has 811 yards and seven touchdowns.
While the Raiders are starting to enjoy success, the Bears are falling apart, sitting at 4-5 and two-and-a-half games out of the final wild card spot.
Then the Raiders traded away their best receiver to the Cowboys for another first round pick, which ended up being Johnathan Abram, who recorded five tackles in his only game before being placed on IR.
Move to this year, the Raiders acquired Antonio Brown for a third and fifth-round pick from the Steelers and then gave up a new contract with $30 million in guaranteed money. We all know what happened with AB in Oakland there after. So while that did not work, the language in AB's contract absolved the Raiders from having to pay any of that guaranteed money and they shipped him off to New England, where he also did not work.
So here we are right now. The Raiders sit at 5-4, a half-game behind a struggling Chiefs team for the AFC West lead, with multiple first-round draft picks in the upcoming NFL Draft, and nearly $72 million in cap space for 2020.
With all that, NFL Hall of Fame quarterback Brett Favre sees Jon Gruden as the NFL Coach of the Year this year.
While there are certainly other candidates to be considered for the award, you can't disagree with the success Gruden is having despite all the backlash he's received.