Key Takeaways

– Mark Davis spent six years chasing Jon Gruden before finally landing him – hiding the pursuit from four interim coaches
– Gruden was handed a 10-year, $100 million contract and full roster control, and immediately replaced GM Reggie McKenzie with Mike Mayock, a first-time GM with zero front office experience
– The results: Khalil Mack trade, Antonio Brown disaster, multiple first-round draft busts, and ultimately Gruden’s resignation after racist/misogynistic emails surfaced
– The piece draws a direct line between the Gruden era’s dysfunction and where the Raiders are today – still searching for stability, now with Tom Brady involved

The Journey

The pursuit lasted six years and required fifteen 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.

From 1998 to 2001, Gruden lifted one of the NFL’s signature franchises back to relevance – the fire-breathing offensive wunderkind who screamed and scowled and set his alarm for 3:17 each morning. Then Al Davis shipped him to Tampa Bay in the middle of the night for two first-round picks, two second-round picks, and $8 million in cash. Twelve months later, Gruden’s Buccaneers routed his old team in Super Bowl XXXVII.

By 2017, it was easier to remember that Super Bowl triumph than the fact that Tampa Bay didn’t win a playoff game in the six years after. Gruden was finishing his ninth season as ESPN’s Monday Night Football color analyst, and his time away only stoked the fascination. The longer he was at ESPN, the more coveted he became.

So when the Raiders crumbled from 6-6 to 6-10 under Jack Del Rio, Davis’ courtship intensified. Sometimes he called 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.

When Gruden finally said yes, Davis stood on stage beaming like he’d won a Super Bowl himself. “Once a Raider, always a Raider,” he said. For 37 minutes he couldn’t wipe the grin off his face. He called it the biggest day of his life.

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

Almost ten years later, the Raiders are again awash in optimism. Fernando Mendoza is two weeks away from being selected No. 1 overall. Tom Brady is in the building. Klint Kubiak is the new coach. Maxx Crosby is still on the roster. And for the first time in a long time, the franchise feels like it has actual direction.

But this franchise has been here before. Davis bought into the hope of a bright future with Gruden, and handed him an unprecedented 10-year, $100 million contract to prove it. In time, Davis learned 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.”

The Kill Tapes

Inside the building, they called them kill tapes.

Months of scouting – trips to the school, conversations with coaches, hours of game tape, Senior Bowl, Combine, pro days – could be trampled in 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, a former staffer remembers, he’d have an assistant compile a short video cut-up of the player’s worst snaps, then show it to all the scouts.

“You can make a player look any way you want,” one source said. “You can make Tom Brady look like a bum.”

When Gruden was handed the keys, he laughed off the notion he wouldn’t work well with incumbent GM Reggie McKenzie. “Reggie will win a lot of ’em,” Gruden said. Within a year, McKenzie was out, replaced by Mike Mayock – a first-time GM straight off a TV set.

“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,” one former employee said.

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.”

Often, the staff would spend weeks studying a free agent and decide he was worth signing. “Then five minutes later, Gruden would storm in and say he’d just talked to his brother Jay and say, ‘This guy sucks, we don’t want him.’ And that was that.”

“Jon was like the wind, man,” one source said. “Every single day you had no idea which way he was going to blow.”

The Mack Trade

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. Ten days before the opener, Gruden called Guenther.

“Guess what? 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? 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?'”

The Antonio Brown Disaster

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. He missed 10 of his first 11 practices, posted his fines on Instagram, slept through meetings, got into a verbal spat with Mayock during a practice in which he called his GM a “cracker,” and was held back by a teammate.

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-show 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 character enough,” one said. “That’s why he whiffed on so many guys.”

The Draft Busts

Thanks to Gruden trading away Mack and later Amari Cooper, 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,” Guenther said. The original plan had been to trade back and grab Ferrell later, 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.

That fourth-rounder was Maxx Crosby. He 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 – proved a hit.

The 2020 draft was worse. Cornerback Damon Arnette, picked seven spots after Ruggs in the first round, was released after a video surfaced showing him threatening someone with guns. Third-rounder Lynn Bowden Jr. was traded five months after the draft. Tanner Muse, a fast-enough-to-clock-a-4.41 safety/linebacker, never made the roster.

Henry Ruggs III remains in prison after a November 2021 crash in which he drove his Corvette at 156 miles an hour and killed a woman. His blood alcohol was twice Nevada’s legal limit.

Two Draft Boards

By 2021, the building was fracturing. The Raiders were now in a sparkling new Las Vegas facility, where the coaches worked on one side of the building, the scouts on another – an old Al Davis maxim designed to prevent them from “buddying up.” The result: 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.'”

That spring, 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 while at ESPN. Gruden is currently suing the league over the leak. A trial date is set for May 2027.

The One That Got Away

Rich Bisaccia, the special teams coach, 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.”