But the National Football League has evolved significantly since Gruden was last in it and to throw such outlay at a coach who has only gone to the playoffs in five of his 11 seasons as a head coach is a substantial gamble that could backfire significantly for a franchise looking for success, stability and good PR heading into the relocation to Las Vegas in 2019 or 2020.
Here are the five biggest takeaways from Gruden's introductory press conference as the next head coach of the Raiders on Tuesday.
The Raiders brought Gruden back with a 10-year deal approaching $100 million.
Cowboys special teams coordinator Rich Bisaccia will be allowed out of his contract to join Gruden, per Rapoport.
"Most of all I love to win and I'm going to do everything I can", Gruden said. After Morton's playing career ended in 1997, he began working in the personnel department for Gruden's Raiders. I've paid very close attention to it. "Number one, I love football". After seven years with the Buccaneers, Gruden was sacked. "But I want to win". They have won 50 games since firing Gruden after the 2008 season.
"I have a lot to prove", Gruden acquiesced.
Gruden succeeds Jack Del Rio, who was sacked following a season-ending loss to the Los Angeles Chargers that capped a disappointing 6-10 campaign for the Raiders. "He's young. He's in his prime", Gruden said of Carr.
Gruden did not elaborate on whether he had final say in personnel decisions but said he would work closely with Raiders general manager Reggie McKenzie.