SKIP BAYLESS: This is either going to be immediately great, or it's going to be, very quickly, an all-time disaster, where you will be able to sit back and say, you know what, out of touch, out of time, out, like it just didn't work.
- What would you determine success to be?
SKIP BAYLESS: Well, you'll see it right away because this is still a pretty good football game.
- It's for the Super Bowl.
SKIP BAYLESS: Not-- I mean, not a Super Bowl. But you're going to see results.
- Oh, 100 million?
SKIP BAYLESS: You're going to see immediate results. They'll be better than they were this year because they weren't very good this year. And everybody thought they were going to be really good this year.
- So for $100 million, I'm buying better than I was last year?
SKIP BAYLESS: I don't think the money matters. In fact, Mark Davis said he's been chasing Jon Gruden for six years, that six straight years, he made trips down to Tampa to try to talk him out of the ESPN Monday Night Football.
- In eight years, he went up by a million until he got to ten per year. And Jon Gruden--
SKIP BAYLESS: You resent that? You jealous of it?
- No. Skip, stop it.
SKIP BAYLESS: I don't know. I think he'll be worth every last penny.
- Unless he brings them a Lombardi, he's not worth it.
SKIP BAYLESS: OK. I think he will bring them a Lombardi.
- OK. Well, then I'm going to be wrong.
SKIP BAYLESS: I think his design is on two years because it sounded to me like he was saying, yesterday, that he came back only because there are two more years in Oakland. He wasn't talking about Las Vegas. I'm not sure he even has any designs on Las Vegas because Jon Gruden-- again, maybe I'm not objective. Maybe I should disqualify myself. I know him pretty well. And I like the heck out of him. And I still believe in him as a football coach because I've told you before, I covered his team in Oakland.
SKIP BAYLESS: And I covered Jimmy Johnson's teams early on in Dallas. He lasted five years. They're both short timers because they've got short fuses that can explode good ways, bad ways. And in this case, Jon Gruden, to me, created a forcefield in Oakland, unlike any I'd experienced, except for that one in Dallas.
SKIP BAYLESS: Those two guys have-- they just spill charisma. There's something about both of them. When Jon Gruden would walk into a TV studio, he would just take it over. You know how he is.
SKIP BAYLESS: That's who he is.
- He's very personable.
SKIP BAYLESS: And I've never seen a better coach fit than Jon Gruden in Oakland because he's got that Chucky persona. And they were all talking about it yesterday. We're talking about the horror movie doll, Chucky, if you don't know him. But Jon looks like him. And he's got that little snarl just like Chucky does. And I think he is Chucky, like he's got Chucky in him.
And I love what some of the ex-players were saying. Jerry Rice is saying, "Chucky is coming." And he was actually warning--
- Jerry a 49er. What are you talking about, Skip? He shouldn't be weighing in.
SKIP BAYLESS: All right? He was there. He was on the scene.
- Skip, what do you know Jerry Rice for? That's like saying you know Joe Montana for The Chiefs.
SKIP BAYLESS: Well, Jerry's got half and half in him, I guess, because he was there.
SKIP BAYLESS: So Jerry Rice is saying, "You'd better be ready for it, Oakland Raiders, because he can either be your best friend or your worst enemy." And that's this guy.
SKIP BAYLESS: So to your point, these kids, with social media and brands, they're going to get challenged the way they've never been challenged. And they're going to go north or south. As Charles Woodson said, great Oakland Raider, he said, "Either you're in or you're out." If you don't respond, you've got to go. What's going to be that-- my way or the highway, right away, next year.
- Because you know what the problem is, Skip? They see him as a TV analyst.
SKIP BAYLESS: They do.
- And the people don't realize--
SKIP BAYLESS: They don't know.
SKIP BAYLESS: You want to talk about in your face?
SKIP BAYLESS: 'Cause I've seen it up close in my face. I know how he can be because he's the charming Chucky figure on TV.
SKIP BAYLESS: It's all fun.
SKIP BAYLESS: But he can be the horror movie Chucky, too.
- Right. Right.
SKIP BAYLESS: So the point is that when you step back from this, you say, OK, what-- like, I'm mystified and sort of amused by your take and every-- it's everybody, not just yours. But you're espousing it, that he's been away for too long. I'm going to remind everybody that for the last-- what was he on ESPN? Nine years.
SKIP BAYLESS: Nine years, all he did was get inside the heads of current players and coaches. I've never seen a coach have the ability to study the game, except for maybe a John Madden, but he could study the game because what did they do every Sunday before the Monday night game? Where were they? They were on the scene, sitting down with the coach and the stars of the team--
SKIP BAYLESS: --where he could pick their brains and get inside their heads.
SKIP BAYLESS: Then what did he do before every draft, the last nine years? He had the ability, the capability of getting inside the heads of every potential high pick quarterback in that draft. Right?
SKIP BAYLESS: So every kid who's come along, who had a chance to be drafted high, has spent quality time with Coach Gruden and his quarterback school.
SKIP BAYLESS: But now you don't have unlimited, unfettered access.
SKIP BAYLESS: I got it.
- You've got limited access to those guys.
SKIP BAYLESS: But don't tell me he's drifted away from the game. He's been studying the game up close, not just game film. He's been getting inside the heads of today's players and coaches.
- But Skip, he's studying the game to be able to break it down. He's not studying the game to come up with game plans and how to win a game. He's not thinking about how the Raiders are going to win-- when he was a TV analyst, he's not studying game tape to see what he can do against this defense. He's just breaking--
SKIP BAYLESS: Sure. He's thinking about it. It's in his blood. His father was a coach. And who's going to call the plays? He's going to call the plays.
- For $10 million, he'd better clean up, too. He should have an offense or a defensive coordinator. As a matter of fact, he should call the defense [INAUDIBLE] also.
SKIP BAYLESS: I believe he will come back as a better coach than he left Oakland because clearly, won a Super Bowl the next year in Tampa. And then they drifted.