Here are the five biggest takeaways from Gruden's introductory press conference as the next head coach of the Raiders on Tuesday.
Two decades after Oakland first presented him as their head coach - the Raiders are once again introducing Jon Gruden as their main man.
"I never wanted to leave the Raiders".
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.
Jon Gruden has returned to the Oakland Raiders after leaving the team in 2001. "I haven't won a game since 2008, but I haven't lost one either".
"For my career to end on that night in New England, it still ticks me off".
Obviously, Gruden has a ton of work to do in the coming weeks and months. "I'm going to do everything I can - no guarantees, no promises - but I want to win".
After going 6-10 in Jack del Rio's second season, the Raiders have chose to appoint a man who took them to the playoffs in two of his four campaigns in charge from 1999 to 2002 and beat them in the Super Bowl XXXVII with the Tampa Bay Buccaneers.
Only one coach has led the Raiders for 10 seasons or more: John Madden.
Gruden downplayed reports from last week that his contract is valued at $100 million over 10 years. "I'm ready for another challenge, and I'm eager to prove I can do it", Gruden said. "There's no question. I haven't coached a game since 2008". I love the players that play it.
Owner Mark Davis was very emotional throughout the press conference, probably because he was gleaming with joy in having Gruden as his head coach and McKenzie as a general manager. Al Davis hired a 34-year-old Gruden to be the team's head coach in 1998.
Gruden wasted little time in addressing his excitement about working with Pro Bowl quarterback Derek Carr while voicing he has already thought about possible plays the team can run, according to James Palmer of The NFL Network. And he also let on that he has been trying to land Jon Gruden for the last six years.