Jon Gruden is failing and has been failing during his second tenure with the Oakland/Las Vegas Raiders. For $100 million over ten years and an ownership stake, I think Mark Davis made an emotional decision to give Gruden the reins to his franchise without realizing that the game had passed Gruden by years ago.

When Jon Gruden took over the Raiders head coaching job in early 2018, he took over a team that had an identity, a solid roster outside of some glaring holes on defense, and a rabid fanbase in Oakland that would physically fight for the Raiders if need be. Their quarterback, Derek Carr, finished third in MVP voting a year before Gruden took over. The Raiders’ offensive line oozed talent and experience with studs like guards Gabe Jackson and Kelechi Osemele and C Rodney Hudson leading the way. They had a perennial Defensive Player of the Year candidate and fantastic leader in Khalil Mack. 

Now? All of these strengths previously mentioned have evaporated and Derek Carr has looked more like his brother David in recent seasons. This paired with Gruden’s inability to draft impactful players has led the Raiders to dysfunction and poor returns in terms of year-to-year record.

Gruden’s record in his second stint with the Raiders is 19-29 after three seasons. Gruden was given a roster that two seasons before went 12-4. 

Given the talent on the roster and Gruden’s price, these results are very disappointing, to say the least. Within their division, The Kansas City Chiefs and Los Angeles Chargers are doing much better from a record and roster standpoint. The one other team within the division, the Denver Broncos, have been dealing with injury-plagued seasons as well as a carousel at quarterback since the departure of Hall of Famer Peyton Manning and a revolving door at the head coaching spot for years, so their dysfunction gets more of a pass than the Raiders. The Chargers in particular moved cities and rebuilt their team on the fly, two things that Gruden was supposed to help facilitate in the move from Oakland to Vegas, but it has yet to come to fruition.

The problems started with Gruden’s alienation of Mack. Gruden claimed he wanted to coach Mack, but when the Chicago Bears swooped in with their offer of two first-round picks, a third-rounder and a sixth-rounder, he could not resist. The deal came at a time when the Raiders did not want to pay Mack the money he demanded (and deserved). Following the trade, the Bears drove Brinks trucks to Mack and paid him over 140 million dollars. Gruden claimed that not paying Mack gave the Raiders flexibility to sign talented players. 

With this flexibility, the Raiders would go on to trade for Antonio Brown. Antonio Brown did not play a singular regular-season game for them. The money also allowed the Raiders to sign tackle Trent Brown and defensive back Lamarcus Joyner. Both of these players no longer play for the Raiders and did not make a lasting impact on the field when they were on the roster. 

Mack would go on to anchor a defense that has remained relevant to this day in Chicago. 

Along with the three players mentioned above, Gruden has whiffed with almost every other free agent signing he has attempted to assimilate with the Raiders. Players such as Jordy Nelson, Vontaze Burfict, Tyrell Williams and Carl Nassib all failed to make a good impression on the field in their own ways. Whether they were washed up or just overrated, it does not matter. 

Gruden clearly does not have the same eye for talent that he used to in terms of free agents. Martavis Bryant also comes to mind when one thinks of Gruden’s failure in this department. Bryant was traded for a third-round pick in the 2018 NFL Draft and was subsequently suspended for more games than touchdown receptions he had during his tenure with the Raiders.

Carr’s career path has unequivocally been altered negatively with Gruden at the helm. 

While his stats have not only plateaued in Gruden’s system, but he also does not look like the quarterback he once was under Jack Del Rio in his 2016 season where he finished third in MVP voting. 

Due to being under the pressure of “the Quarterback Guru” more than he ever was under the previous regime, Carr has not looked confident in his decision-making with added responsibility. 

Even adding a stud at running back in Josh Jacobs has not changed much for Carr as his stats have not changed in the time since Jacobs has joined the team. 

Gruden traded talent on both sides of the football in order to build a team with “his guys” and that has led to players on both sides of the football to regress or being alienated. In Gruden’s first year back with the Raiders, Carr was sacked an astronomically high 51 times with an offensive line that held higher expectations previously given the personnel and highly touted prospects added. 

First-round pick Kolton Miller had initially failed at protecting Carr’s blindside at left tackle, allowing 23 sacks in his first two years in the league and fellow rookie Brandon Parker would end up being a very expensive turnstile for this once-vaunted group. 

Though Carr’s stats increased narrowly, this led to a lot more being asked of Carr in his first year in Gruden’s complicated system that led to the team finishing 4-12 on the season. 

The current iteration of the Raiders offensive line no longer features Jackson, Hudson or Brown as all three have either been deemed too expensive or a liability in Gruden’s eyes.

Kolton Miller has progressed slightly each season from his rookie year, allowing four sacks in 2020, a huge step up from the previous two years. However, this limited sight of progress has earned Miller a questionably high three-year, $54.015 million contract extension with $42.6 million guaranteed after the 2020 season.

Finally, the biggest part of Gruden’s failure during this second tenure lies in his inability to bring in talent that has positively affected the product on the field for the Raiders through the draft. 

His drafting has been mediocre at best partnered with his inability to bring in impact-free agents who will help the team. Players, and now afterthoughts, such as Kolton Miller (glorified traffic cone), DT PJ Hall (on a different team), Brandon Parker (19 games started in three seasons), DE Clelin Ferrell (six sacks in two seasons), S Johnathan Abram (two forced turnovers in two years), CB Damon Arnette (can’t hold a starting position) and HB/WR Lynn Bowden Jr. (zero snaps played for the Raiders) have all either flopped completely or been sub-mediocre on the field. One of the only bright spots when looking at Gruden’s draft record during this time is previously mentioned running back Josh Jacobs.

With Grudens’ defenses in Las Vegas being nothing special year after year and his offensive line falling apart since he arrived, it is clear that Gruden’s eye for younger talent/talent, in general, has led to the Raiders being stuck in purgatory.