​Jon Gruden has already charted an unconventional NFL life. He became the head coach of the Oakland Raiders in 1998 and then jumped to the Tampa Bay Buccaneers in 2002, winning a Super Bowl in his first season and hanging around until 2008. Then he spent nine years as an analyst on “Monday Night Football,” which at the time was arguably the most prestigious booth on television. He returned to Oakland in 2018 and stayed with the franchise through its move to Las Vegas before resigning five games into the 2021 campaign.A deluge of controversy did not prevent him from catching on with Barstool Sports, where he showcases his one-of-a-kind personality covering the league he loves. There is the occasional rumor connecting him to an open coaching gig, but it sounds like Gruden is keeping all of his options open.AdvertisementAdvertisementAdvertisementOn a recent episode of the “Ira Kaufmann Podcast” the former ball coach dropped an interesting nugget.“I was a broadcaster for nine years; hell’s bells,” Gruden said. “I want to be play-by-play. You know, Frank Gifford, he transitioned into the play-by-play role. I would like to transition. I had nine years of watching these guys — [Mike] Tirico. And I’d like to give that a shot, man.”As Gruden mentioned, such a switch has been done before. Sort of. Gifford handled play-by-play duties on “Monday Night Football” from 1971-1985 before transitioning to an analyst role when Al Michaels came aboard in 1986. Gifford would then step in for Michaels when he was covering postseason baseball. The point is, broadcasters can contain multitudes.AdvertisementAdvertisementAdvertisementGruden’s complicated relationship with the NFL would seem to make a return to calling professional action unlikely. But there is no shortage of collegiate games for him to cut his teeth on if he’s serious about the endeavor. Considering his name recognition, it feels like only a matter of time until some network decides such a gamble would be worthwhile.— Enjoy free coverage of the top news & trending stories on The Big Lead —