If anyone can make it work, I'd bet on Gruden

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MamaRAMa
Apparently Gruden as the next Raiders HC is the real deal. ESPN is reporting it'll be announced at a Raiders news conference on Tuesday. Yes, Gruden has been an analyst for the past 8 years but he's been out of coaching for so long and the game and rules have changed. It's a completely different animal to be waching the game from a booth or on film and to have it all in your head than being down in the weeds with all those egos and dripping sweat. I'm going to wish him the best, but my gut tells me it's not gonna work out.

Yes, he's been out of the game for a long time. And there's a good chance you're right that it won't work out. That said, in some ways our own Sean McVay is a lesser version of Gruden. Jon's an intense student of the game, and apparently he's "blessed" (if you agree it's a blessing) with a crazy ability to live with only 3 or so hours of sleep a night without actually needing more. So he spends a ton of time working. If anyone can get back up to speed, I'd bet on Jon Gruden. Wouldn't be surprised to see him have a lot more success than other recent retreads.

Or consider this: Vermeil was more of a dinosaur than Gruden and that worked out in the end.