“Are You … Kidding Me?” The Khalil Mack Trade Continues to Haunt Jon Gruden

The Raiders picked up an overtime victory against the Browns on Sunday, giving Jon Gruden his first regular season NFL victory in nearly 10 years. And yet, he still couldn’t escape the looming shadow of Khalil Mack.

NFL.com columnist Mike Silver paints a picture of the Raiders head coach’s first win since November 30, 2008, which leads with a behind-the-scenes snapshot of Gruden lamenting the loss of his former star defender just hours before his team kicked off a few time zones away:

As he readied his game face for what he hoped would be his first NFL head-coaching victory in exactly nine years and 10 months, Jon Gruden sat in the coaches’ area of the home locker room at the Oakland Coliseum on Sunday morning, scrolled through his cell phone and got some decidedly disturbing news.

“Damn –??Khalil Mack??had??another??strip sack?” Gruden asked rhetorically, shaking his head at the??Oakland Raiders??assistant coaches in his midst. “Are you … kidding me?”

“Are you … kidding me?” is the exact same thing we find ourselves saying every week when Mack does something amazing.

So, nope. We’re not “…” kidding you, Coach. That’s four forced fumbles in four games for the NFL’s highest-paid defensive player who cut his teeth with the Raiders, earning three Pro Bowl appearances and a pair of first-team All-Pro nominations along the way. Mack has five sacks, a pick-six, 24 pressures, and is Pro Football Focus’ highest-rated edge rusher with a league-best 92.1 grade.

Gruden has offered up some strange thoughts regarding the trade since pulling the trigger on the mega-deal at the end of the preseason. He tried to deflect blame and point fingers by saying Mack didn’t want to play in Oakland, then shared an odd thought about the difficulty in finding good pass-rush help when his team struggled to get to other team’s quarterbacks. But at least Gruden has come off as someone with a little more self-awareness with his most recent comments compared to his original thoughts on the matter.

Either way, thanks again, Jon. Bears fans appreciate your help in starting the year with a 3-1 record and a spot atop the NFC North standings.

written by

Luis C. Medina, who you can find on Twitter at lcm1986, has been covering the Chicago Bears at Bleacher Nation since 2017. Since then, he has written about 3 head coaches, 5 play-callers, and 11 starting quarterbacks. Previously, Luis wrote about the Cubs and MLB at BN (2015-16) and worked in the Chicago Tribune sports department (2011-16). He also co-hosted a Cubs postgame show, Outside the Ivy, in 2019.

more bears news

Thomas Brown Speaks: Box vs. Sideline, Preparing for the Vikings, More

Chicago Bears Interim Head Coach Thomas Brown met with the media on Thursday and immediately announced a slight tweak to the team's weekly schedule. For the remainder of the season, Wednesdays will be walk-through days to preserve the players' bodies...

Caleb Williams Speaks: Thoughts On Extended Losing Streak, Vote of Confidence For Poles, More

Thanks to the Monday Night Football game this week, Caleb Williams met with the media on Thursday (instead of Wednesday) at Halas Hall, and he said something that made me chuckle. "Seasons like this happen every once in a while,"...

Chicago Bears Injury Report: Two Running Backs Get DNPs

A pair of Chicago Bears running backs did not participate in the team's first practice in preparation ahead of the Monday Night Football showdown against the Minnesota Vikings. Starter D'Andre Swift and top backup Roschon Johnson were non-participants in Thursday's...

Thanks to Caleb Williams, the Chicago Bears *ARE* Seen as a Top Job Opening

If the Chicago Bears head coach opening is going to be as coveted as the team thinks, it can thank rookie quarterback Caleb Williams. To be clear, this isn't just me spouting off as a Bears fan. NFL Network insider...

New Report Confirms Bears View Mike Vrabel as a “Top Candidate” For Head Coaching Job

It feels like so often when the Bears are presented with what feels like obvious choices, they pivot to something different. Bruce Arians is available and wants the job? Let's actually hire a CFL head coach. We're going to draft...

Did the Bears Pass on Bill Belichick to Target Ben Johnson in Their Head Coach Search?

It still boggles my mind that Bill Belichick will be coaching college football in 2025. And while I do not believe the Chicago Bears were an ideal fit for Belichick at this stage of his coaching career, there is a...

The Belichickian Prophecy, Time to Play With Pride, 2024 NFL Draft Re-do, and Other Bears Bullets

I goofed yesterday. It slipped my mind that ??? because the Chicago Bears were playing on Monday Night Football this week ??? their regularly scheduled media availability would be pushed back a day. So instead of getting Interim Head Coach...

REPORT: No NFL Teams Reached Out to Bill Belichick Before Taking North Carolina Job

The only thing more surprising than legendary NFL coach Bill Belichick taking his talents to the University of North Carolina is that no NFL teams reached out to him before he signed on to lead the Tar Heels football program....

Scratch Bill Belichick From the List of Potential Bears Head Coaching Candidates

The Chicago Bears have four games remaining, but that's not stopping the world from hypothesizing who their next head coach may be when the dust settles. One of the names mentioned in that conversation has been former New England Patriots...

This Field Yates Mock Draft at ESPN Would be a Dream Scenario

Get ready to familiarize yourself with Will Campbell, because his name is going to come up in a bunch of mock drafts as a Chicago Bears target between now and when the NFL Draft begins. Field Yates has the Bears...

Latest News

Chicago Bears Injury Report: Two Running Backs Get DNPs

A pair of Chicago Bears running backs did not participate in the team's first practice in preparation ahead of the Monday Night Football showdown against the Minnesota Vikings. Starter D'Andre Swift and top backup Roschon Johnson were non-participants in Thursday's...

As Patrick Williams Returns, Will He Have to Adjust to a Bench Role?

The Chicago Bulls will approach Patrick Williams' return with caution. The forward has missed the team's last 10 games after experiencing foot inflammation following a Nov. 18 victory over the Detroit Pistons. He was finally able to return to the...

Yes, Isaac Paredes Would Hit a Crap-Ton of Home Runs in Houston’s Ballpark

With folks traveling out of Dallas later yesterday and on into today, and people maybe exhaling a bit after a whirlwind Winter Meetings, I am not necessarily shocked that it's been radio silent on the Kyle Tucker trade rumors. I...

Caleb Williams Speaks: Thoughts On Extended Losing Streak, Vote of Confidence For Poles, More

Thanks to the Monday Night Football game this week, Caleb Williams met with the media on Thursday (instead of Wednesday) at Halas Hall, and he said something that made me chuckle. "Seasons like this happen every once in a while,"...

Thomas Brown Speaks: Box vs. Sideline, Preparing for the Vikings, More

Chicago Bears Interim Head Coach Thomas Brown met with the media on Thursday and immediately announced a slight tweak to the team's weekly schedule. For the remainder of the season, Wednesdays will be walk-through days to preserve the players' bodies...

Thanks to Caleb Williams, the Chicago Bears *ARE* Seen as a Top Job Opening

If the Chicago Bears head coach opening is going to be as coveted as the team thinks, it can thank rookie quarterback Caleb Williams. To be clear, this isn't just me spouting off as a Bears fan. NFL Network insider...

Pirates Reportedly Listening on Mitch Keller AND Jared Jones?

Bit of a weird rumor coming out of the Winter Meetings from Pittsburgh, where the Pirates are reportedly open to moving starting pitchers Mitch Keller and Jared Jones. Indeed, the language used in the report by the Post-Gazette was that...

New Report Confirms Bears View Mike Vrabel as a “Top Candidate” For Head Coaching Job

It feels like so often when the Bears are presented with what feels like obvious choices, they pivot to something different. Bruce Arians is available and wants the job? Let's actually hire a CFL head coach. We're going to draft...

Did the Bears Pass on Bill Belichick to Target Ben Johnson in Their Head Coach Search?

It still boggles my mind that Bill Belichick will be coaching college football in 2025. And while I do not believe the Chicago Bears were an ideal fit for Belichick at this stage of his coaching career, there is a...

Can Matas Buzelis Climb the Rookie Ladder? Josh Giddey’s Next Deal, NBA Cup Drama, and Other Bulls Bullets

It feels like the Chicago Bulls haven't played in forever! Put some respect on Matas Buzelis' name. NBA dot com recently revealed their updated rookie ladder, and the Chicago Bulls' No. 11 pick failed to make an appearance yet again....

more bears news