Inside Jon Gruden’s disastrous second run with the Raiders

The pursuit lasted six years and required 15 cross-country flights.

Mark Davis hid them all from the four head coaches he churned through after his father’s death in 2011. The Oakland Raiders were now his team, and in his mind, there was only one man who could save them.

Jon Gruden had done it before. It was in Oakland where Gruden first became a coaching star, the fire-breathing offensive wunderkind who screamed and scowled and boasted to reporters that he set his alarm for 3:17 each morning. From 1998 to 2001 he lifted one of the NFL’s signature franchises back to relevance, only to be shipped to Tampa Bay in the middle of the night for two first-round picks, two second-round picks and $8 million in cash — Al Davis’ way of ending a contract dispute. Twelve months later, Gruden’s Buccaneers routed his old team in Super Bowl XXXVII.

By 2017, it was much easier to remember Gruden’s Super Bowl triumph than the fact that Tampa Bay didn’t win a single playoff game in the six years that followed. He was finishing his ninth season as the color analyst on ESPN’s “Monday Night Football,” and his time away only stoked the fascination of NFL owners. The longer Gruden was at ESPN, the more coveted a candidate he became, chased not only by Davis but also the Indianapolis Colts’ Jim Irsay, who earlier that year tried to pair Gruden with franchise icon Peyton Manning in an executive role. Rumors that Gruden might take a top college job at Tennessee, where he had once been a graduate assistant, persisted for years. He seemed to relish the interest, allowing his reputation to burnish with each coaching cycle.

So when the Raiders crumbled from 6-6 to 6-10 in their third season under Jack Del Rio, Davis’ courtship of Gruden intensified. Sometimes Davis called him in the middle of the night. Sometimes he called just before kickoff. One Raiders staffer caught the two in an elevator at the team hotel the night before a Week 16 loss in Philadelphia, a game Gruden called in the ESPN booth the next day.

A few weeks later, Gruden decided he was in. It had taken calls to his wife and his mother, plus all those trips to Tampa, where Davis visited so often he not only had a favorite hotel but a favorite laundromat, too. The owner beamed from atop the stage at the introductory news conference, smiling as if he’d won a Super Bowl. “Once a Raider, always a Raider,” he began. For 37 minutes Davis couldn’t wipe the grin off his face. He called it the biggest day of his life. He said his dream had come true.

“This is a big effin’ deal,” he bragged.

Almost 10 years later, the Raiders are again awash in optimism. In two weeks, they’re likely to land Heisman Trophy winner Fernando Mendoza with the top pick in the 2026 NFL Draft. NFL legend Tom Brady is calling the shots after buying a minority stake in the team in 2024. New coach Klint Kubiak is fresh off a Super Bowl run with the Seattle Seahawks. And defensive lynchpin Maxx Crosby is, for now, still on the roster.

But this franchise has been here before, buying into the hope of a bright future. Davis thought the Gruden hire would revive The Raider Way — the sharpest mind in the game, the polished prodigy coming back to kick everyone’s ass — and he was willing to hand Gruden an unprecedented 10-year, $100 million contract to prove it. In time, the owner would learn Gruden was far from the football savant he played on TV.

As one former Raiders exec summed up the experience: “It was all just so desperate.”

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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.

“It wasn’t reflective of all the work you did,” said one team source — who, like others for this story, was granted anonymity to speak freely about his experiences working for the organization. “You can make a player look any way you want. You can make Tom Brady look like a bum.”

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. They’d sit there in silence, swallowing their words. Gruden, who declined to comment for this story, could still coach, still scheme, and at times, still lead. “He just needed to stay the f— away from evaluating talent and building the roster,” one former team employee said.

He couldn’t.

When Gruden was handed the keys to the franchise, he laughed off the notion he wouldn’t work well with the team’s incumbent general manager, Reggie McKenzie. “Reggie will win a lot of ’em,” Gruden said of any potential personnel tussles with the former NFL linebacker. “He’s a lot bigger than me.” Within a year, McKenzie was out, replaced by a first-time GM straight off a TV set.

In other words, Mike Mayock was not someone who could tell Jon Gruden no.

“When you see an established coach bring in a GM who’s never done the job, it’s 100 percent because the coach wants to run the building and manipulate things exactly how he likes them,” said a former team employee.

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.)

When it came to roster construction, Gruden had a type the pro scouting staff came to know well: “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.

“That was Gruden’s crutch,” one source said. “This happens around the league with some coaches — they just want their guys. They don’t wanna teach or develop.”

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.”

Paul Guenther signed on as Gruden’s defensive coordinator in 2018. A few months later, on the verge of free agency, Gruden tossed him a question: hand out a massive extension to the team’s best defensive player or use that money to re-sign five serviceable starters? “Well,” Guenther said, “I took this job to coach Khalil Mack.” The Raiders let the five starters walk.

Four months later, Mack, the 2016 Defensive Player of the Year, still hadn’t signed his deal. Guenther got a call 10 days before the opener. “Guess what?” he remembers Gruden telling him. “I just traded Khalil Mack for two first-round picks.”

“Jon, we just let five starters walk out the door, and now Khalil’s gone?” Guenther said. “We got nobody left.”

The Raiders went 4-12 that year and gave up the most points in the league. “Khalil was the heart and soul of our team,” one source said. “So when you trade him, you’re telling everyone he’s not good enough. The rest of the players are wondering, ‘How am I gonna be good enough?’”

Thanks to Gruden trading away another top talent — wideout Amari Cooper was sent to Dallas midseason — the Raiders had a stash of premium picks ahead of the 2019 draft: three first-rounders and a fourth inside the top 40. It should have been the foundation of a rebuild. It wasn’t.

The Raiders missed badly with their first selection, gambling on Clemson edge Clelin Ferrell fourth overall despite considerable pushback in the building. “The grades were all over the board on him, from the scouts to the coaches,” Guenther said. The original plan had been to trade back and grab Ferrell later in the first round, but on the clock, the Raiders panicked. By August, the staff was starting to grow nervous. “We had this fourth-rounder out of Eastern Michigan outplaying the No. 4 pick in the draft every single day,” one source said. Indeed, that fourth-rounder, Crosby, remains the shrewdest pick the Raiders made in a decade.

Of those four picks inside the top 40, 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.

Still, despite an uneven first draft together, Gruden and Mayock had reason to believe: Thanks to the coach’s persistence, one of the league’s most dynamic offensive weapons was on his way to Oakland.

Antonio Brown arrived for training camp in the summer of 2019 in a helicopter. His feet were frostbitten from a cryotherapy session in Paris. He was at odds with both the league and the Raiders over his helmet; the one he’d used for nine seasons in Pittsburgh had since been banned. The seven-time Pro Bowl wideout missed 10 of his first 11 practices, posted his fines on Instagram, slept through meetings — and torched the Oakland secondary in the rare instances he was on the field. He got into a verbal spat with Mayock during a practice in which he called his GM a “cracker” and had to be held back by teammate Vontaze Burfict. The Raiders released Brown before he ever played a snap.

“I don’t think that guy ever intended on playing football for us,” a source said.

“It was just a s—how from Day 1,” Mayock added.

The miss on Brown, several sources indicated, spoke to Gruden’s biggest weakness. He’d get blinded by talent, believing he could outcoach any ancillary issue. “Jon didn’t respect a player’s football background or football character enough,” one said. “That’s why he whiffed on so many guys.”

Davis, who declined to comment through a team spokesperson, could be both odd and indignant, former employees said. One remembers him screaming at his mother on the team plane when the Wi-Fi didn’t work; another time, he complained about play calls loudly enough for the offensive coordinator to hear but wouldn’t address the issue directly with the coach.

“One time, on a flight home after a loss, one of the assistant coaches asked someone from IT to help him with his computer,” the staffer remembers. “Afterwards the IT person walks away and says, ‘What’s the point? He’s gonna be gone in a couple of months anyway.’ We had 12 games left! I just can’t imagine anywhere else in the league where the coaches are being talked down to by the IT staff. But that’s the way it had been there forever.”

Davis, the former employees said, was as hands-off as they come, sleeping in most mornings and never involving himself in personnel decisions. “He has no idea what he’s doing,” one former staffer said. “He thinks just like a fan.” Al Davis had worked his way up the coaching ranks and served as the commissioner of the American Football League before taking over the Raiders. His son was simply handed the team.

“In a way, he’s great to work for because he lets you do your thing,” one former employee said. “But he’s nothing like his dad. He doesn’t know anything football. ‘Oh, my dad liked fast guys? Where are all the fast guys?’ … It was all about The Raider Way. That thinking is so archaic. It’s not even relevant anymore. They gotta be good football players, too.”

Tanner Muse was a fast guy — fast enough to clock a 4.41 in the 40-yard dash ahead of the 2020 NFL Draft. But when Mayock lobbied to take the Clemson safety/linebacker in the third round, the room was split. “He was one of those guys who looked the part and ran well, but he was a horrible football player,” one former staffer said. Muse never made the roster, and the Raiders’ 2020 draft class dissolved into one of the worst in recent memory. Within 18 months, four of the first five picks were off the team.

Henry Ruggs III remains in prison after a November 2021 accident in which he slammed his Corvette into the back of a woman’s Toyota Rav4 at 156 miles an hour, killing her. Ruggs’ blood alcohol content was twice Nevada’s legal limit. Cornerback Damon Arnette, picked seven spots after Ruggs in the first round, was released a month later after a video surfaced showing him threatening someone’s life and brandishing multiple guns. Third-rounder Lynn Bowden Jr. was long gone, traded five months after the draft amid struggles in training camp, when the team started to worry he would become a bad influence on Ruggs and Arnette.

A former Boston College safety selected by the Steelers in the 10th round in 1981, Mayock had earned league-wide respect for his work as a draft analyst on NFL Network but never worked in an NFL front office. He leaned heavily on his No. 2, director of pro personnel Dwayne Joseph, and while his scouts loved working for him — “Greatest guy of all the GMs I’ve worked for,” one said. “If you did the work, Mike valued your opinion,” added another — his lack of acumen showed. “He just didn’t know how NFL front offices worked.”

Mayock’s inexperience in the role, coupled with Gruden’s gruff unpredictability, left the Raiders in a constant state of chaos. The Brown trade was a disaster. The coach had shipped away two of the team’s best players. The draft misses emptied the roster of young talent, and the reaches in free agency kept piling up. “You’re always playing with rental clubs,” Guenther said. “We had so few guys who were homegrown.” In private moments, Mayock would shake his head and steam. “We’re doing something dysfunctional,” he’d tell himself. “We’ve gotta fix it.”

They never did. By 2021, the building started to splinter. The Raiders were now in a sparkling new facility in Las Vegas, where the coaches worked on one side of the building, the scouts another — an old Al Davis maxim designed to prevent them from “buddying up,” one former staffer said. The result was two separate draft boards, one stacked by Gruden and the coaches, the second by Mayock and the scouts. Confusion reigned.

“I worked for six other head coaches and three other GMs, and I’ve never heard of a team having two draft boards,” one former staffer said. “I told myself, ‘There’s no way we’re gonna survive this.’”

The Raiders whiffed on another first-round pick that spring, when Gruden let offensive line coach Tom Cable talk him into drafting Alabama tackle Alex Leatherwood 17th overall. “Alex was a freak athlete, but you gotta do the scouting,” one source said. Leatherwood was cut before his second season.

By then, Gruden was gone. He resigned five games into his fourth season after The New York Times uncovered a slew of racist and misogynistic emails he’d sent Bruce Allen, his former GM in Tampa, while working for ESPN. Gruden, currently an analyst with Barstool Sports, is suing the league, alleging the NFL intentionally leaked the emails. A trial date is set for May 2027.

Special teams coach Rich Bisaccia, whom Mayock had known since their days as college counselors at the Joe Namath Football Camp in the 1970s, took over on an interim basis. The Raiders won their final four regular-season games — earning the franchise’s second playoff berth since 2002 — before dropping a wild-card heartbreaker in Cincinnati. After the playoff loss, Mayock pushed for the interim tag to be removed from Bisaccia’s title. Instead, Davis fired both.

“Had they kept Bisaccia,” Mayock says now, “they’d be chasing (AFC) West division championships as opposed to the first pick in the draft.”

With that first pick, the Raiders are expected to take Mendoza, whom the team hopes will usher in a new era in Las Vegas. Thanks to the failed trade with Baltimore, Crosby is still on the roster. And second-year GM John Spytek shelled out $281.5 million in contracts during the initial wave of free agency, upping the talent for a team that’s needed to do so for years.

“Antonio (Pierce) was given a s— roster. Pete (Carroll) was given a s— roster,” one source said of the Raiders’ two coaches to precede Kubiak. “The underlying issue is that Mark has never really respected the GM position. He let Gruden pick Mayock. Then he let Josh McDaniels pick his best friend as GM, Dave Ziegler. Now he lets Tom Brady do the same thing with Spytek.”

Davis has made it clear in recent years that Brady will have his say in football decisions. What remains uncertain is if the Raiders will ever get it right.

Out of the GM seat for four years now, Mayock goes back to a conversation he once had with a highly successful head coach. “I asked him, ‘How many teams do you really worry about on an annual basis?’ The coach looked at me, thought for a second, then said, ‘Six or seven, max.’ I said, ‘Why so few?’ And he said, ‘Mike, the other 25 will eliminate themselves.’”