Yes, yes, yes, this subject comes up quite a bit. The Raiders fans still have stars in their eyes for "Chucky" and what might have been had Al Davis not traded away his last successful coach. And those stars will remain bright so long as the Raiders struggles continue.
Mark Davis spoke at length with Gruden in the past year and as the close to another 4-win season was approaching, there were some thought/hoped Gruden might replace Dennis Allen as head coach. Davis may just have been one of those hoping that could happen as well.
Gruden brought Rich Gannon to the Raiders in the late nineties and the two had great success together with the Raiders. Right up until they faced each other in the Super Bowl and Gruden got the best of his old quarterback. The two remain great friends so if the was anyone to ask about Gruden's mindset with regard to his coaching plans, it would be Gannon.
"I think he's gonna coach," Gannon said of Gruden in an interview on 95.7 The Game. "I think he wants to coach, but he's in a great situation. He's making a ton of money at ESPN, he's watching his kids grow up, he's getting to spend more time around the home which I think has been important to him and to Cindy. But trust me, I've had conversations with him. We seem to have them every off-season. He talks about he still has a desire to come back and coach and how competitive he is. And you know what's interesting is he still loves the Raiders. I know that to be true because he's told me so. He loves the Bay Area, he loves the Oakland Raiders, and I think the world of Reggie and Dennis, I want to see them get this thing turned around, but you know what, who knows? Strangers things have happened. We'll see how it all turns out but Jon I think will definitely coach at some point, just don't know where."
Gruden said similar things back in September of last year as the Raiders were about to play on Monday Night Football.
"I do get the itch a lot. I miss it tremendously," said Gruden. ". . . I do have an ambition to coach some day."
"I grew up with the Raiders. Even though my dad didn't coach for the Raiders, I grew up a Raider fan and yes, absolutely I consider myself a Raider. You should see my house. I got a nice little room where you would think I'm still with the Raiders. A Raider room. I got a lot of old memorabilia. . . I like the mystique of the Raiders and I like being a part of it."
Despite his itch and love for the Raiders, it sounds like Jon would like to see his kids grow up if possible before he returns to the grind and time commitment of being a head coach. If that's true, it could be a while before he puts on an NFL headset. His youngest son, Jayson, is 13-years old which would mean it would be at least another four years before he graduates high school and heads off to college.
Gruden also signed a 5-year deal with ESPN in 2011 which has him calling games for the Network as part of their Monday Night Football telecast through the 2016 season. He has said he intends to honor his contract which would mean three more seasons before he throws his visor back in the ring to coach.
Then again, you just never know. When Gruden was talking with Mark Davis last season following his first presence at Raiders training camp since his departure 12 years earlier, it stirred up much talk of his returning to the coaching ranks. That talk will continue every off-season and if those voices as well as those in Jon's head/heart get too loud to ignore, anything can happen.