This was in the summer of 2000, back when Jon Gruden was still the impossibly young coach of the Oakland Raiders fighting a team owner stuck in the past. We were walking across a threadbare field at the team’s training camp – a makeshift operation set up behind a country hotel – and he kept shaking his head at the tufts of grass that looked like islands in an ocean of dirt. His face was a mix of disgust at the shoddy conditions and pride for the way he made the best of them.

“Look at this,” he said with a laugh.

Nothing about owner Al Davis’s Raiders screamed first-class in those days. That was the charm of the league’s most dysfunctional franchise. You didn’t need to be fancy to roll in Davis’s roughshod outfit. When Davis hired Gruden in 1998, one of the coach’s greatest selling points was that, as a 35-year-old, he came cheap.

And yet he had been a brilliant choice for Davis, a taskmaster driven to make a flophouse of a franchise right. The season before his hire, the Raiders had practically quit on their season, with one star showing up to practice clad in a fur coat. Now two years into the revival, Gruden had given the team some character.

But Gruden’s two respectable 8-8 seasons (they had gone 7-9 and 4-12 in the two years before his arrival) had not pleased Davis. Gruden didn’t run the owner’s beloved vertical passing offense, choosing instead the more deliberate but effective West Coast system learned from his mentor Mike Holmgren. So even with Gruden about to push the Raiders to within a game of the Super Bowl in the 2000 season, rumors flew that Gruden’s rebuild was going to cost him his job. As we walked that day I asked him about the whispers.

He stopped. He scowled.

“I don’t have a conscious fear of failure,” he said.

Then he smiled.

“I kind of like the rumors,” he added. “It’s part of the job.”

Watching Gruden this week, as he sat at a dais with Davis’s son Mark, after accepting a contract that could pay him up to $100m to revive the Raiders again, I wondered if it was possible for him to be that cocksure young man on the broken football field. He is in his mid-50s now with a snug security that coaches never get: guaranteed employment for the next 10 years. He’s lived the past nine seasons in the comfort of the broadcast booth – still attached to football but safely removed from the grind that devours coaches’ souls.

Nobody had to light a fire inside the Gruden who stood on that worn practice field nearly 18 years ago. His ticket to infamy came in winning his fight with Al Davis and the old Raider way. But that was before the Super Bowl he won with Tampa Bay, before he appeared to tire of coaching, before the Gruden Grinders on TV, before Gruden’s Quarterback Camp, before Gruden became a brand. Coaching isn’t the same when you boast a cult of personality.

Who knows if he can spark his new team, but doing so after years away isn’t easy. In 2004, Washington’s legendary coach Joe Gibbs left broadcasting and returned to the franchise where he had won three Super Bowls in the 1980s. Like Gruden, Gibbs had become a name, running a successful racing team. He had moderate success in the four seasons that became known as “Gibbs 2.0” twice squeaking into the playoffs as a wild card but never coming close to the greatness of before.

When Gibbs left again, at 67, he seemed drained, worn from the rigor of coaching in a modern age.

Gibbs loved to talk about the all-nighters he and his staff pulled while game-planning during the season. He’d refer to the joy of hearing the early-morning trash trucks as he toiled under the office lights. The young Gruden liked to boast of his own endless hours spent at work. On the day we talked in 2000 a reporter had told Gruden he wanted to follow the coach through his workday. Gruden roared with laughter and suggested they meet a little before 4am at a favorite convenience store to grab coffee.

Later that afternoon he stopped practice, angry that the Raiders defensive players – who were dominating the workouts that day – had been taunting their team-mates on offense. He called the entire team to the middle of the field. He shouted about respect, about dignity, about “playing like a champion”. His players dropped their heads. They listened. There were no more taunts the rest of practice.

Can this Gruden stop practices for lectures the way he once did? Will he want to? On television he seems like he was back then: hyper, aggressive, growling at things that displeased him. But now he has set a new standard for coach’s pay, blowing apart the old structure and signaling an era where coaches might become as wealthy as the best players they coach.

Al Davis never would have given a coach $100m, but Al Davis has been dead more than six years now. The Raiders will soon leave Oakland and their tired old stadium for an extravagant palace just off the Las Vegas strip. Gruden won’t be the gritty young coach on the barren field any more. He will be a man making $100m in a city where the nights glow and nothing is real.

Is that enough to make the Raiders great once more? Or just an expensive grab at a mirage from the past?