Before his failed second stint with the Las Vegas Raiders, Jon Gruden was widely considered to be a legendary figure. His maiden voyage as the head coach of the Silver and Black was successful, and then he won a Super Bowl with the Tampa Bay Buccaneers.
After that, he became an entertaining analyst for ESPN and famously ran his Gruden QB Camp before the annual NFL Draft in April. And in recent years, he's carved out a niche as an internet personality with Barstool Sports. The football world has largely treated Gruden well.
But those years in between were an absolute nightmare for the franchise and Raider Nation. His grand return, which seemed inevitable with Mark Davis calling the shots, was an all style, no substance venture that left the fanbase with a horribly bad taste in their mouth that they're yet to get rid of.
New intel about Gruden's second stint with the organization has now surfaced, however, thanks to The Athletic's Zak Keefer. And if fans thought that things were a nightmare before, they must have forgotten that there are eight Chucky movies. This horror show was worse than anyone imagined.
Jon Gruden's second stint was so much worse than Las Vegas Raiders fans thought
Keefer's story begins with Davis' pursuit of Gruden, which he described as rather desperate and clinging to the past. Instead of doing the work to hire a great head coach in Oakland, Davis wanted to rekindle the flame that his late father, Al, abruptly blew out when he traded Gruden to Tampa Bay.
And the chase, which included 15 cross-country flights, lasted for six years before Davis got Gruden in his grasp. Keeper noted that one former Raiders executive summed up the experience: “It was all just so desperate.”
Fans always had a feeling that Gruden was all-too-powerful in the building, using charged emotions and rash decisions to essentially run the franchise. Keefer's piece serves as a mountain of evidence for that claim, and the stories are just simply unbelievable to read.
"Inside the building, they called them kill tapes.
"Months of scouting — trips to the school, conversations with coaches, hours of game tape, Senior Bowl, NFL Combine and pro day workouts — could be trampled in a matter of minutes, subject to the ever-shifting moods of the man in charge. Gruden strolled through the doors in Oakland in 2018 with undisputed authority, and if he wasn’t in on a prospect, former staffers remember, he’d have one of his assistants compile a short video cut-up of the player’s worst snaps, then show it to all the scouts.
"Some veteran personnel men would push back against Gruden once in a while, but the less experienced ones did not. When the coach unleashed a kill tape on one of their prospects, they knew it was over."
That certainly doesn't sound like a man who has the organization's best interest at heart. And it showed in the draft, as the Raiders made puzzling decision after puzzling decision. Many thought that Gruden was trying to be the smartest guy in the room. Maybe it was as simple as him being erratic.
His partnership with general manager Reggie McKenzie only lasted one season, and when Gruden wanted to bring in Mike Mayock as his general manager, those in the building knew what that meant: Gruden needed a puppet, so he got someone who had never done the job before.
When Gruden arrived, he immediately began operating this way. According to Keefer's article, Gruden lied through his teeth to an incumbent member of the staff and essentially just wanted to surround himself with "Yes men."
"This was Gruden’s show. One game management exec who’d been with the team several years was told by the coach that he’d get an opportunity to interview for his job. He spent weeks preparing, studying Gruden’s background, system and tendencies, even turning down opportunities with other NFL clubs. Then the Raiders’ head of security called. “What’s a good address to send all your stuff to?” he asked.
"There would be no interview. The explanation he got a few days later offered little solace: “Jon heard analytics in your title and wanted nothing to do with you.” (The Raiders, fifth in the league in challenge success rate during the exec’s time there, quickly became one of the worst in football. In 2019 alone, Gruden went 1-for-10 on coach’s challenges.)"
Although it's not that funny, Raider Nation should feel vindicated reading this next bit. Fans always joked that Gruden was stuck in the past with some of the veterans that he brought into the building, and it sounds like the team's supporters weren't the only ones to notice that.
“'Jon loved veterans who were All-Pros like eight years ago and were on their way out to pasture,' one source said. 'Anyone who had a name he remembered or had a big game against him in the past,' another said. When those types of players became available via the league’s transaction wire, the scouting staff would chuckle, knowing Mayock would get the question as soon as he stepped out to practice."
Jason Witten, anyone?
But it was even worse than that. Gruden would apparently undermine the hard work done by his pro scouting staff once free agency came around because he thought he knew better. Time ultimately proved that he did not.
"Often, the staff would spend weeks studying a free agent and ultimately decide he was worth signing. 'Then five minutes later, Gruden would storm in and say he’d just talked to his brother Jay (the head coach in Washington from 2014-19) and say, ‘This guy sucks, we don’t want him.’ And that was that,' one source said. 'Jon was like the wind, man. Every single day you had no idea which way he was going to blow.'”
Keefer also touched on the Khalil Mack trade debacle, which they botched from the outset. Defensive coordinator Paul Guenther noted that the team opted to keep Mack and let five starting defenders walk in free agency, and Gruden almost celebrated the eventual trade in a phone call with Guenther.
Mayock has since owned the Clelin Ferrell pick, which was ill-advised. Keefer spokes to sources in the building who indicated that Las Vegas liked Ferrell in a trade-back situation, but they simply panicked once they got on the clock, as if the top three picks weren't pretty set in stone that year.
The Antonio Brown saga was the perfect encapsulation of how Gruden was, according to those whom Keefer talked to in the building. He overlooked character concerns and put football talent above all else, believing that he could simply outcoach any off-the-field issues. His hubris backfired on him.
This story doesn't paint Mark Davis in a great light either, as they cite him being too disconnected and hands-off, and generally cultivating, or turning a blind eye to, a hostile work environment that he created by hiring Gruden in the first place.
Several other examples were brought up of the Raiders' draft snafus, like Tanner Muse, Henry Ruggs III, Damon Arnette, Lynn Bowden Jr., and Alex Leatherwood. All of these players failed for different reasons, but all roads seemingly led back to a lack of vetting or attention to detail on Gruden's part.
During that era, however, Las Vegas was known for whiffing early and finding value, or downright stars, in the later rounds. That is the only reason this team stayed afloat. And Keefer may have revealed an obvious reason why.
"Of those four picks inside the top 40 (in 2019), only running back Josh Jacobs — whom Mayock had to convince Gruden to come around on, according to some in the room — proved a hit. By the third day of the draft, the coach’s interest waned. 'Gruden basically wasn’t even around for that part,' one source said. It’s when Mayock did some of his best work: Crosby in the fourth, tight end Foster Moreau 31 picks later, wideout Hunter Renfrow in the fifth."
Stories about the Raiders' coaching staff and scouting department having two separate draft boards are emblematic of just how dysfunctional things were under Gruden's watch. And things wouldn't have gotten better; Gruden was seemingly stuck in his ways and unwilling to listen.
However, the football gods finally interfered, or in Gruden's opinion, the NFL did. He was forced to resign in disgrace after several of his offensive emails were leaked. Honestly, it was a satisfying way for him to end his tenure: A real Mea culpa moment where everyone knew he was to blame.
Again, Raider Nation knew that things were bad under Gruden. They watched the games and heard bits and pieces from reporters. But this is an unbelievable takedown of Gruden during his second tenure and makes things appear far, far worse than fans could have ever imagined.
Gruden was a one-man show, and ultimately, a one-man wrecking crew that led to his own demise.