From the time he stepped off the sidelines and into the broadcast booth in 2009, Jon Gruden was considered a “top candidate” for countless coaching vacancies in the NFL. It turns out, there was really only one job the now former “Monday Night Football” color analyst ever really wanted.

“I can’t believe how much he loves the Raiders,” longtime sports talker and host of the official Oakland Raiders podcast J.T. the Brick said on Mile High Sports AM 1340 | FM 104.7 this week. He spoke with Nate Lundy and TJ Carpenter one day after Gruden’s introductory press conference.

“He won a Super Bowl with Tampa Bay and beat the Raiders, lost in the ‘tuck rule’ game with the Raiders in New England and I think that loss has eaten at him his entire career,” he continued.

That loss — in the 2001 AFC Divisional round — is one of the key reasons Gruden may have passed on the countless coaching opportunities that came his way between his firing with the Tampa Bay Buccaneers in 2009 and his decision to return to the Raiders for the 2018 season and beyond.

“He has an unbelievable relationship with Mark Davis,” J.T. told Lundy and Carpenter. “He loves the Raiders alumni / legends. Forty-eight of his former players — legends and players — showed up at the press conference. That has never happened in NFL history for a retirement press conference, let alone a hiring press conference. And I really feel like he has unfinished business. He doesn’t like the way it ended in Oakland.”

Broncos fans will remember that former Raiders owner Al Davis traded Gruden for Tampa Bay’s 2002 and 2003 first-round draft picks, 2002 and 2004 second-round draft picks, and $8 million in cash.

“As he told me last night on the radio and he said yesterday at the press conference, he never wanted to leave,” J.T. said. “The sincerity in his voice, and how badly he wanted to come back and end it with the Raiders, showed yesterday. He’s happy to be back, and he’s got unfinished business.”

Some of that unfinished business is improving on a 1-7 record against the Denver Broncos as head coach of the Raiders. Much of that is returning Oakland to the playoffs, something they have done just once since Gruden defeated Bill Callahan in Super Bowl XXXVII. The biggest piece may be his role as flag-bearer when the team relocates to Las Vegas.

“That’s the $64,000 question,” J.T. said when asked if the move was timed in part to generate some buzz ahead of the move. “Mark Davis is importing Jon Gruden for six or seven years. So, it doesn’t matter what happened with Jack Del Rio. As soon as Gruden said he was ready, he was going to have that job. Now, Mark Davis needs to build a stadium and sell PSLs (personal seat licenses) in Vegas. Jon Gruden is the perfect guy to do it.”

That doesn’t mean Gruden will ignore the fans in Oakland, however.

“Let me leave you with this,” J.T. said. “The biggest takeaway from yesterday is Gruden’s passion for Oakland. You’re not going to hear about Las Vegas in the next couple of years coming from Gruden. You’ll hear it from the Raiders and their organization that they have boots on the ground already and they’re building that stadium in Vegas, which is going to be right behind Jerry’s World (AT&T Stadium in Arlington) as the best stadium in all of football. But Jon Gruden doesn’t want to talk about Vegas. He really wants to win in Oakland.

“The irony of all this is that Jack Del Rio was more “Oakland” than even Jon Gruden. He grew up in Hayward, 10 minutes away from the Coliseum. That was his boyhood dream — to coach the Raiders — and he lost that job because a guy named Jon Gruden, who’s a rockstar, wanted that job back. I can’t believe that Gruden, who was recently inducted into the Ring of Honor in Tampa, won a Super Bowl with Tampa, cared more about the Raiders and winning in Oakland than he does about Tampa Bay and his legacy there. He wants his legacy to be the Oakland Raiders. I think, again, it goes back to that “tuck rule” game where the NFL screwed the Raiders. Gruden thought he was going to win the Super Bowl that year. And since then, it hasn’t been right for the Raiders. They haven’t been a winning organization. They haven’t won on the field. And Gruden believes that that’s his legacy. He’s the guy to get the Raiders back. It’s just a question, can he do it before they move to Vegas or is it going to hit the ground in Vegas when they finally get good?”

Sorry – this audio content is no longer available., including his thoughts on Raiders roster moves that might result from Gruden’s hiring, or listen in the podcast below.

Sorry – this audio content is no longer available.

Catch Mornings at 5280 with Nate Lundy, Shawn Drotar and TJ Carpenter every weekday from 7a-9a on Mile High Sports AM 1340 | FM 104.7 or stream live any time for the best local coverage of Colorado sports from Denver’s biggest sports talk lineup. Download the new mobile app for Apple or Android.