Oakland Raiders head coach Jon Gruden is clearly still in mourning over losing defensive star Khalil Mack to the Chicago Bears and this is really the first time he's spoken out about it.

Mack went on to lead the Bears defense to establish them in the elite category as well as get them the first place spot in the NFC North for the first time in nearly a decade.

Despite missing a couple of games in the 2018 season, Mack accumulated 12.5 sacks, a career-high six forced fumbles, and a career-high four passes defended. To say Mack had a good season would be an understatement and Gruden was only able to watch Mack's success from afar.

The Raiders traded a once in a generation type of a player in Mack and while the Bears are normally at the bottom of the division, Gruden saw a possible lottery pick turn into a pick in the 20's. The same can be said about their trade that sent wide receiver Amari Cooper to the Dallas Cowboys.

At the time of the Cooper trade, the Cowboys were horrendous, but once the trade went through, the Cowboys went on quite the win streak. Two picks that Gruden thought may have been top-10 wound up in the 20's and it's likely the two players he traded away were responsible for the success.

All Gruden can hope to do now is make the most of the picks he has, but unless the Raiders hit a home run in the first round they'll have a lot of making up to do.