Owner Mark Davis reportedly is preparing such a proposal which could include an ownership stake in the franchise.
There are other complications, as well. Gruden is represented by the same agent, Bob LaMonte, as Del Rio, which leads to several delicate situations.
The idea that Gruden will flame out is as reckless as saying he's going suddenly make them into Super Bowl favorites.
Add the fact that Gruden's former scheme is borderline Downing-esque and the Raiders have tried this before with Shell only for it to end in disaster - and fans have a right to be frightened by the notion of Chucky's return.
"I don't want to sit here and speculate", Gruden said per the Oakland Tribune's Jerry McDonald. "There is no news to report", Gruden said. I take a lot of phone calls from coaches, some others ... yeah, sometimes owners.
One ownership source told ESPN that the owners "might not be so quick to approve the deal" because they wouldn't want to set a precedent. "Im here to help people".
Gruden has yet to say either way whether or not he's interested in the Oakland job - a job he previously held from 1998 to 2001 before leaving to coach the Tampa Bay Buccaneers.
He won the Super Bowl in his first season with Tampa Bay, defeating his old Raider team.
"The owner", one source said about Davis, "has an affinity for him".
In his 11 year career, Gruden is 95-81 as a head coach.
An ESPN report says the Oakland Raiders are planning to pursue Jon Gruden to bring him back as head coach. More and more, it looks as if this is it. Even though he signed a four-year extension last offseason, the Raiders have fallen below.500 in 2017.
But it might be a different home that Gruden goes back to next season.
Pegging landing spots for Gruden from year to year has become a sport within the sport, but many believe it is different this year.
Even though Gruden has been hesitate in the past to return to coaching, he will have enough power within the organization that he can reshape the entire front office and coaching staff, though some holdovers still remain from his first time coaching the team.
So, is Gruden the next man up for the Raiders?
"Just about every year, I talk about coming back to coach".
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