For years, teams have wondered how to lure Jon Gruden out of retirement, but it turns out all he wanted was a good quarterback and $100 million.

Raiders are giving new head coach Jon Gruden a 10-year contract, the longest coaching deal in NFL history, sources tell ESPN. The deal is likely to be worth about $100 million. — Adam Schefter (@AdamSchefter) January 5, 2018

It’s unknown whether Gruden’s new contract also comes with the lifetime use of a private jet, but it’s safe to say the coach has found his beach — or, when the franchise makes it to Las Vegas, his desert. It’s unknown how much of the $100 million is guaranteed, but if Gruden gets the full value of the contract he’ll make nearly 20 percent of owner Mark Davis’s net worth, which is estimated to be around $500 million. Not bad for a coach whose career winning percentage (.540) is barely above Marvin Lewis’s (.527).

This is a massive gamble for a team that hasn’t even made it to Las Vegas yet. Gruden has been one of the most sought-after coaching candidates for 10 years, and Oakland winning the #GrudenGrinder sweepstakes is a victory in the buzz department, but it’s unclear how NFL-ready he is, or what he could do to live up to this contract. Gruden retired from the NFL coaching life of sleeping in his office and got to see his kids grow up, which is admirable, but it also means that he’s been out of the game. Now Oakland has handed a decade-long contract to a guy who hasn’t coached in 10 years.

Granted, Gruden’s track record looks impeccable from a distance. He was the head coach in Oakland for four seasons until owner Al Davis traded him to a stacked Tampa Bay Buccaneers team before the 2002 season. The Bucs went on to beat the Raiders in the Super Bowl that year — a John Wick–level revenge tour — and got the ring that has made the coach a white whale for the Raiders in recent years. It’s important to note, though, that Gruden inherited a stacked roster with Hall of Fame talent that included Warren Sapp, Simeon Rice, Derrick Brooks, and Ronde Barber. After that Super Bowl, the Bucs under Gruden won seven, five, 11, four, nine, and nine games and went 0–2 in the playoffs before he was fired. Since then, the sport has undergone a passing revolution, and Gruden has watched it happen from the booth instead of the sideline.

According to The MMQB’s Albert Breer, Gruden has been a longtime subject of fascination for Mark Davis, the son of Al Davis. Breer writes that the Raiders drafted quarterback Derek Carr at Davis’s behest in part to win back Gruden, who praised the quarterback out of Fresno State before the 2014 NFL draft. Even Carr and $100 million may not comprise the entire draw for Gruden — ESPN reported last week that Davis was prepared to offer him a stake in the team’s ownership. In Oakland’s favor is that nobody is more loyal to their teams than Jon Gruden. In 2003, the South Bend native told Playboy that he lost his virginity while listening to the Notre Dame fight song.

“There was a band?” asked Playboy.

“No, not even music,” Gruden replied. “But it was in my mind.”

Clearly the man is dedicated, and he’s famously energetic — he woke up every day during his head coaching career at 3:17 a.m. to that same Notre Dame fight song — but his television persona seems to have bloated his résumé. One hundred million dollars over 10 years isn’t Super Bowl money, it’s dynasty money. Gruden got his payday, but now he has the impossible task of living up to his myth.