After nine years in media hibernation, Jon Gruden’s head-coaching reboot began with the first victory every new hire desperately wants.

He won the introductory news conference.

Wearing a sharp gray suit and speaking with an even sharper silver tongue, Gruden unfurled a pitch that he has spent nearly a decade crafting – hitting familiar motivational touchstones about being ready to work and locking the doors and living only once. Sitting by Gruden’s side, Oakland Raiders owner Mark Davis couldn’t have smiled any wider, eager to steady his relocating franchise and buy his way past a failed 2017 season.

Years from now, in success or failure, Tuesday’s news conference will be one of the defining snapshots: two men and a franchise reunited at the intersection of desperation and opportunity and a lot of money. Both winning something on Day 1 of their NFL reconciliation but neither knowing how this will work out.

If you take anything away from Tuesday, take this: Jon Gruden just reentered the NFL completely on his chosen terms – richer, more powerful and with bigger expectations than ever before. He waited for the perfect window and Mark Davis opened it wider than anyone could have imagined. Now Gruden is a $100 million man with Belichickean control. What he does with it will be one of the most-watched storylines of the NFL’s next decade. And not just from the perspective of NFL fans, but also from league executives and coaches who have watched Gruden from afar and marveled over what one NFC personnel man called “ESPN’s reputation inflation.”

Make no mistake, there is a massive gamble here. The Raiders are betting $100 million on Gruden being some semblance of the young, driven, almost maniacal head coach who rocketed to fame two decades ago. The guy who first lit a fire under a moribund Raiders franchise and then took Tony Dungy’s Tampa Bay Buccaneers roster to the Super Bowl mountaintop when Dungy couldn’t finish the job. The same guy who seized his Lombardi Trophy as a head coach at the age of 39, with seemingly everything laid out in front of him.

When Davis envisions Gruden, this is the image he is paying for. The Jerry Bruckheimer-esque hype video that introduced Gruden’s return was proof Tuesday.

But that’s where this gets interesting. There is a distinct undercurrent of skepticism about Gruden in many NFL corners. One where conversations about him and his onetime status as an offensive “genius” – not to mention numerous job rumors over the years – have birthed some pointed questions. Wonderings such as …

Why does a guy who professes his love so much for coaching spend almost a decade in the media world?

How does a guy who transformed so few quarterbacks as a head coach (arguably Rich Gannon and nobody else) become the media’s armchair authority on quarterbacks?

Why does the first five years of Gruden’s head-coaching résumé – when he revived the Raiders and then won a Super Bowl in his first year with Tampa Bay – greatly overshadow his last six years on the sideline, when Gruden went 45-53, including a pair of disappointing playoff losses?

As one longtime NFL executive put it, “Gruden and Marvin Lewis have almost identical winning percentages as head coaches and Marvin has done it [four years] longer. But one guy walks on water every offseason and the other is always on the hot seat.”

It’s an interesting thought. Perhaps that’s what a Super Bowl ring and an extended high-profile pause from the sideline buy in today’s NFL – a renewed thirst for employment, to the tune of $100 million. Whatever the difference, if this is a league about wins and losses, Gruden is getting the benefit of the doubt other guys didn’t. After all, Brian Billick had a better winning percentage in his nine years in Baltimore and won a Super Bowl. But he was never considered the charismatic media machine that Gruden became at ESPN, and never became a serious candidate for another NFL head-coaching job. Barry Switzer won a title with someone else’s players, too, and finished 47-29 in the NFL. But he was old and controversial. Said funny stuff, too – but not funny and promotable, like “Spider 2 Y Banana.”

None of this is to say the Raiders made a mistake. Gruden could come back after nine years away and pull a Dick Vermeil, showing an amazing ability to motivate and reinvent parts of himself in his Act III as a head coach. That’s what Gruden is selling – that he knows he has a lot to prove, knows he has to adapt to new concepts, knows that he faces a learning curve. But he notes, convincingly, that his nine years away were spent in a perch that allowed him front-row access to all the changes in the NFL.

“I’ve got to see every facility in the league,” Gruden said Tuesday. “I’ve had a chance to watch them practice – see how they conduct training camps. I’ve had a chance to learn some things and see some things that I would have never gotten to see as a coach. I’ve had a chance to study different offenses, different defenses. I’ve had a chance to get into personnel more. I think I’m more big picture now than I was in the past.”

If that’s true – if Gruden has learned to see a bigger picture – he should showcase that right out of the gate in his return.

The challenges are waiting for him in the locker room. You could argue that the emphasis on safety and longevity have changed the mindset of players more in the past 10 years than any decade before it. You could argue that rules changes and shifts in the college game have leveled the field for the offensive geniuses who once had the market cornered on wide-open schemes. And you could also argue that analytics and revolutions in scouting and data analysis have closed the gap between good coaches and great coaches.

Or you could just look at Bill Belichick and say it’s the same as it always was: the greatest NFL coaches with the greatest NFL quarterbacks are worth their weight in gold. At the very least, Gruden enters 2018 with his quarterback on the roster, and his weight in gold in the contract details.

All that’s left is proving he can still be great after the news conference is over.

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