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The Raiders’ Jon Gruden Experiment Remains Just As Confounding As Ever

In January 2018, Oakland handed Gruden a 10-year, $100 million deal. Since then, he’s been a laughingstock, a surprise success, and virtually everything in between. What should we make of the first two years of the hire that rocked the football world?

Dan Evans

On the day that Jon Gruden was introduced as the new face of the Oakland Raiders—as it happens, the once (he was also head coach for four years starting in 1998) and future (his deal is good through the end of the 2027-2028 season) face—the total population of people who believed this to be a wise, canny, or otherwise judicious decision might have been counted on one hand. Or one finger, maybe, representing a man with a bowl cut and a running tab at P.F. Chang’s.

Mark Davis spent the duration of the presser looking about as happy as any mammal without a tail to wag can, a human manifestation of a yellow lab greeting its just-returned-from-deployment owner, maybe a few days after a grooming job gone wrong. The Raiders owner stopped short, thankfully, of licking the man of the hour’s face, but he beamed around the room, at the cameras, at his team’s new head coach, and directed a comment at Gruden’s family: “I’d like to thank them from the bottom of my heart for making my dream come true.”

For Gruden, this may well have been a shared dream. How could it not, for the coach turned on-air analyst who would end his decade-long absence from the NFL for a $100 million, 10-year contract and a boss seemingly willing to march into war, or at least the Black Hole, on his behalf? But whether Gruden shared Davis’s gleeful optimism about his ability to transmogrify the Raiders—well, that’s another question.

In this, at least, he wouldn’t be alone: No one’s ever really known what to make of Gruden. Or at least, every time they thought they did, they were wrong.

There was a moment, just a few short weeks ago, when you might have thought that the 2019 Raiders were for real. This was a surprising development, to put it mildly, given that the Raiders’ plan for 2019—add Antonio Brown, bake at 350 degrees, serve—disintegrated before the season even began. The team spent August unhappily hosting HBO Sports and NFL Films’ Hard Knocks, a show whose thesis statement—look at these suckers, they really think they can do it!—does not generally lend itself to the documentation of great football teams.

But then somehow these suckers were doing it. Coming out of Week 11, Oakland was 6-4 and had won three straight games. The team was not merely in the running for a wild-card berth—it was just a game behind the Chiefs for supremacy of the AFC West. The Raiders were set to face off against Kansas City in Week 13; the Chiefs had a bye in between, so all Oakland needed to do was beat the lowly Jets and they’d arrive at their divisional showdown with identical records and, who knows, maybe make us all look dumb for ever doubting them in the first place. Derek Carr vs. Patrick Mahomes, an apparently even fight.

Except, well, things didn’t quite go the Raiders’ way. They lost to the Jets the way a carcass loses to a turkey vulture: ugly, smelly, and without a lot of dignity for either party. Instead of carrying on the winning streak, they instead fell 34-3, a first-quarter field goal the Silver and Black’s lone score. Then the Raiders limped into Kansas City, where they were shelled, 40-9, pushing the AFC West out of reach and the wild card close to it. Now they’ve made it three straight losses, being throttled Sunday by the surging Titans, 42-21, and leaving them with a, ah, 1 percent chance of making the playoffs, per The New York Times.

In recent weeks, pretty much everything that could go to crap for the Raiders has. Carr, facing tough defenses, has looked lousy; his offense made it 147 straight plays without posting a touchdown, and lost star rookie Josh Jacobs to a shoulder injury. The team’s defense, meanwhile, was shredded, unable to muster much of anything to stop Mahomes, Ryan Tannehill, or, uh, Sam Darnold. And, yes, the coaching has looked subpar, too. “I take credit for all that went wrong,” Gruden said after the loss to the Jets, so sure, let’s give it to him. But let’s also acknowledge that up until the calamity began, the coach’s plan for his team somehow seemed to be working.

Call it another case of Gruden whiplash, courtesy of the coach who has spent the better part of three decades confounding the NFL, or at least those of us who pay attention to it.

When he first joined the Raiders in the ’90s, Gruden was anointed “Chucky” for his resemblance to a certain redheaded murder doll. He was, at 34, the youngest head coach in the NFL, and, with his Raiders transforming into a powerhouse in the space of just a few years—they led the AFC West in 2000 and 2001—he became a kind of proto–Sean McVay, an unparalleled wunderkind destined for greatness. (McVay, in fact, got his professional start a decade later as an assistant wide receivers coach under Gruden in Tampa Bay.)

He decamped to Tampa Bay to start the 2002 season, part of one of the late Al Davis’s last pieces of brash strategery. That year, Gruden led the Buccaneers to their first-ever Super Bowl victory—over none other than the Raiders.

But those earlier Midas-like years were followed by a stall; after a string of ho-hum seasons, he was sent packing in 2009.

So then Gruden moved to ESPN, where he became a color commentator on Monday Night Football. He was, again, an overnight sensation. If Tony Romo has been hailed for his connection to the game—well, the buzz was that and more when Gruden entered the booth. Less than a decade after being anointed “the perfect NFL coach” in Sports Illustrated, his turn to generalism got him called “America’s football coach” in no less than The New Yorker.

In time, though, as he became a personality on other ESPN properties, he morphed into caricature. See: the “Gruden Grinders,” or Gruden’s QB Camp, or the myriad other shticks trotted out as your next favorite catchphrase.

Watching him on TV, you could be sure, sometimes, that this guy never really had the goods, that the Tampa Bay ring was at least in part good luck, that all that wunderkind stuff was hogwash: He was an entertainer, and nothing more.

Unless, that is, it was all a cover. The longer Gruden sat in the broadcaster’s chair, the louder the rumors seemed to grow that he was just biding his time before he returned to coach once again. It’s an image he seemed to enjoy cultivating, taking reporters to his personal strip-mall office HQ, where he, not for nothing, insisted he had been carefully dissecting the NFL, day in and day out, using every day he was away from the league to study its secrets, its teams, their strengths and weaknesses.

It was only natural that he would be courted by teams, or maybe courted by teams, or definitely not courted by teams, no siree. Consider that during his decade on ESPN he was linked to: the Chargers, the Eagles, the Rams, the University of Texas. He was reportedly headed back to Tampa Bay, or else to Oakland, long before he actually was. Did he have some barbecue in Knoxvilleahem? Sometimes Gruden stoked the rumors himself—“I’m preparing myself to come back,” he said in 2017—only to immediately deny them. “I don’t foresee myself coaching anytime soon,” he said, three weeks before he was, at long last, hired back by the Raiders.

When Mark Davis lured Gruden back to the league with the richest coaching deal in NFL history—well, it made a kind of sense. That is, the coaching, and coaching in Oakland, parts made sense. But the 10 years, the tenth-of-a-billion, for a guy who maybe was a genius or maybe wasn’t? For a franchise just on the precipice of moving to a new city, and needing to put new butts in a new stadium? You could only shake your head: what a hustle.

In the time Gruden was away from the Raiders, from 2001 to 2018, the team went through nine additional head coaches, of which only one, Jack del Rio, managed even to crack .500. JaMarcus Russell happened, as did an intra-coach brawl that left an assistant coach with a broken jaw. The team made it to the playoffs just twice in that time: that Super Bowl loss to Gruden’s Bucs, and then a 2016 wild-card appearance doomed by Carr having broken his leg at the end of the regular season. The Raiders could go the whole of Gruden’s decade-long contract without making the playoffs, in fact, and that still wouldn’t be their longest drought this century. If Gruden brings only ignominy to the Raiders, it won’t even be very notable.

But there was a certain case to be made for optimism when he arrived. After all, that winter’s playoff face-plant was easily explained. Take a healthy Carr and young stars Khalil Mack and Amari Cooper, add a steady hand to guide the ship and, well—you could see the way forward, finally.

Except that Gruden didn’t take that path. He traded Mack to the Bears for peanuts—one of which sprouted, after much doubt from fans and media alike, into Jacobs, who was the AFC Offensive Rookie of the Month in October and November—and shipped Cooper off to Dallas. He made it clear that he didn’t think much of Carr, either, though somehow Nathan Peterman has turned out not to be the answer, either. Then he hired Mike Mayock, an old NFL Network pal, to be the team’s new GM last winter, and, well, “I don’t know what my man the Gru-dog is doing,” quoth his old Monday Night Football partner, Sean McDonough.

It is not exactly, or at least entirely, the Gru-dog’s fault that his plan for 2019 fell apart. The Brown deal went belly up before the season even began, with Hard Knocks incidentally along to capture the chaos (well, kind of). The star wide receiver, having forced the Steelers to trade him to Oakland in the offseason, missed nearly all of training camp due to a cryotherapy mishap and a labyrinthine dispute over gear. Just as Brown was preparing to play at last, a dispute over timeliness escalated first into Brown releasing a recording of Gruden (the coach thought it was “awesome,” reportedly), and finally to the Raiders cutting him outright. (Brown subsequently signed with the Patriots, and then a former trainer came forward to say that he raped her. Brown played one game with New England and was then cut.)

But then, even with the team’s central architecture having disappeared before the season could even begin, there were the Raiders winning. There they were in line for the wild card. There they were ready to challenge Mahomes and the Chiefs. I believed. Maybe you believed, too. And then the clock struck midnight and the Raiders are just the 6-7, mediocre Raiders again and it’s anyone’s guess as to whether Gruden knows, or has even known, or will ever know, what he’s doing.