Envisioning the doomsday scenario for Jon Gruden’s tenure in Oakland doesn’t require much imagination. The Raiders head coach hasn’t roamed an NFL sideline in 10 years. That also happens to be the length of his new contract, which is set to pay him a cool $100 million over the next decade. As franchises have increasingly found success behind 30-something head coaches in the mold of Sean McVay, the Black Hole has bet on a 54-year-old former Monday Night Football announcer who last coached a playoff team when Calvin Johnson, Adrian Peterson, and Joe Thomas were rookies.

Gruden hasn’t helped measures by showing his players film from decades before they were born and signing aging talent like the 33-year-old Jordy Nelson while at the reins of a revamped front-office power structure. But as easy as the Jon Gruden, football dinosaur jokes might be, Chucky’s second tenure in Oakland remains a great unknown. Anyone who says they have even the slightest idea about how this will work out is lying through their teeth.

“We’ll be watching film, and out of nowhere Coach Gruden [will say], ‘Derek, call the play. Where are you doing with it? What’s the coverage? What’s the corner’s technique?’ And I’m answering: bam, bam, bam. Like that, every meeting.” —Raiders quarterback Derek Carr

After a training camp practice Thursday, Raiders quarterback Derek Carr spoke with a group of assembled reporters about what it’s been like to learn from Gruden over the past six months. The environment he described sounded like football utopia for an ambitious quarterback. And from the way Carr tells it, the specifics of his job have changed considerably with Gruden in charge. Carr made it clear that his feelings for departed head coach Jack Del Rio and former quarterbacks coach Todd Downing run deep, but has embraced having an established QB guru at the helm. “It’s awesome,” Carr says. “I absolutely love it. He wants me to be at the front of the room, showing [everyone] how I do it, from my voice. Just the way the quarterback position is treated, the way he’s a quarterback guy as the head coach, is completely different.”

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That’s a familiar refrain among quarterbacks who spend the early parts of their careers playing for defense-first head coaches before coming to work with offensive-oriented leaders. And while there are plenty of examples of defensive-minded head coaches overseeing an offensive renaissance—see: Dan Quinn and the 2016 Falcons—the day-to-day transformation for a quarterback with a head coach like Gruden is undeniable. “The demand is different,” Carr says. “We even meet differently. We’ll be watching film, and out of nowhere, Coach Gruden [will say], ‘Derek, call the play. Where are you doing with it? What’s the coverage? What’s the corner’s technique?’ And I’m answering: bam, bam, bam. Like that, every meeting.”

Carr’s standing within the league’s quarterback hierarchy has shifted dramatically over the past two years. When the Raiders went 12-4 in 2016 as Carr threw for 3,937 yards with 28 touchdowns to lead a unit that was eighth in Football Outsiders’ offensive DVOA, the perception was that the Fresno State product had emerged as the star of the next generation of QBs, the heir apparent to the Manning, Brady, and Brees mantle. Even those who didn’t feel Carr’s tape necessarily matched his reputation conceded that the Raiders were set under center for years to come.

Derek Carr

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Over the past year, though, factors both within and outside of Carr’s control have altered that outlook. As young quarterbacks like Carson Wentz and Deshaun Watson have taken the league by storm, the now-27-year-old Carr has begun to feel like an afterthought. As he enters his fifth season, on the heels of an underwhelming 6-10 campaign, it’d be easy to assume that he’s a finished product. With a $25 million cap hit due in 2018 and $125 million potentially coming his way over a five-year deal signed in June 2017, Carr has completed the pivot from prized asset on a rookie contract to pricey veteran who must be a consistent top-tier passer to provide any value.

The optimistic spin is that Gruden could help Carr keep improving. Five years may feel like a wealth of experience for an NFL quarterback, but history has proved that leaps remain possible as signal-callers age. Matt Ryan ascended to a higher plane at age 30 under then–offensive coordinator Kyle Shanahan. Matthew Stafford has only recently displayed a new gauge while working with Jim Bob Cooter, and the Lions QB entered the league five years before Carr did. The most fitting example might be the last quarterback whom Gruden guided in Oakland. Rich Gannon was 34 and coming off his 13th NFL season when he went to his first Pro Bowl following the 1999 campaign, Gruden’s second with the Raiders. Three years later, Gannon was MVP of the league.

Massive jumps in production are possible when circumstances drastically change. And that’s what Carr says has happened in Oakland. Carr notes that he meets with Gruden multiple times each day, in both formal and casual settings. When Carr isn’t in a meeting, he’s usually chatting with Gruden. When other quarterbacks are taking practice reps, Carr’s standing at Gruden’s side, breaking everything down. Hell, Carr is almost with Gruden even when the two aren’t together. “The other night I was dreaming of him calling a play, so I’ll just say [I’m with him] 24 hours,” Carr jokes. “We’re always thinking of the next play, the next call, the next adjustment. I think he’s brainwashed me a little bit. I’m kind of like his quarterback robot.”

“We’re always thinking of the next play, the next call, the next adjustment. I think [Jon Gruden’s] brainwashed me a little bit. I’m kind of like his quarterback robot.” —Derek Carr

That nonstop interaction has given Carr a look at his coach’s ocean of football knowledge, which is so vast that it’s hard to comprehend. The jokes come fast when a relic from a past NFL generation shows his team footage from the 1960s and ’70s, but Carr insists Gruden’s backlog of information is a product of how much tape he churns through. “I don’t think there’s a play ever run in football that he hasn’t seen on game tape,” Carr says. “I’ll stick by that for the rest of my life. He had some practice film of me at the Senior Bowl of a route we were installing. That’s how much he watches football.”

Gruden’s résumé is fascinating because of the stops he’s made, and also because of just how many of young coaches have put in time at his feet. Gruden may seem like a striking departure from the likes of McVay and Shanahan, but go see where both of them started. No, really. Go check.

That’s right: The NFL’s two offensive wunderkinds du jour both started out as low-level assistants for Gruden’s Buccaneers in the mid-to-late 2000s. While Gruden’s rhetoric and signings have understandably given analysts pause about his place in the modern game, the most effective schemes in today’s league have the bones of his West Coast principles.

There’s a chance that Oakland’s Gruden experiment will turn out to be the NFL’s $100 million version of the Hindenburg. The Raiders could resemble a team straight out of 2002, in both their schematics and personnel choices, which Gruden seems to possess a troubling amount of control over. But it’s also possible that the new dynamic between Gruden and Carr will spark a resurgence for a quarterback still in the early phase of his career. If Gruden can pull the most out of Carr this season and beyond, what initially seemed like a cavalier choice will go down as a resounding success. “We should be on the same page,” Carr says of his relationship with Gruden. “We should think the same way. There should be no secrets between us. I know where he’s at. He knows where I’m at. Just having that open relationship like that with the head coach—so open that other people see it—that’s just good for the football team.”