One of the youngest NFL head coaches to win a Super Bowl is looking to return to the sport, but it won’t be on the sidelines.Legendary Tampa Bay Buccaneers leader Jon Gruden currently works with Barstool Sports, but has ambitions to return to play-by-play duties.Gruden was inducted into the Buccaneers’ Ring of Honor in 2017GettyIn an exclusive interview with Ira Kaufman, Gruden expressed his desire to return to the broadcasting booth.“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.”Gruden served as an analyst for ESPN’s Monday Night Football broadcasts from 2009-2017.He also served in roles for the network’s coverage of the NFL Draft and postseason college football games.Before joining ESPN, Gruden had just finished a six-year stint with the Buccaneers, famously winning Super Bowl XXXVII.The 48-21 win over the Oakland Raiders made the 39-year-old Gruden the youngest head coach to win a Vince Lombardi at the time.This record was soon surpassed by Pittsburgh Steelers‘ Mike Tomlin, who himself is transitioning into a broadcasting career.Gruden signed an extension with ESPN in 2014 which made him the highest paid personality at the network, but the contract had an interesting clause.Gruden won Super Bowl XXXVII with the Buccaneers, making him the youngest head coach to win a Vince Lombardi at the timeGettyFollowing his exit from the Bucs, Gruden spent nine years working at ESPNGettyThe deal contained an opt-out that allowed him to return to coaching if he so pleased, and that’s exactly what he did.The Raiders announced the return of Gruden as head coach on January 6, 2018, signing a 10-year, $100 million contract.Gruden would guide the Raiders to a 4-12 record in his first year back, before 7-9 (2019) and 8-8 (2020) records in the following seasons.The Raiders began 2021 with a 3-2 record, before Gruden resigned following a league investigation into the head coach over workplace misconduct.Gruden’s interest in returning to the booth is clear, but a return would come with challenges.His departure from the Raiders in 2021 came alongside a highly publicized lawsuit against the NFL and Commissioner Roger Goodell.Gruden’s lawsuit against the NFL and Roger Goodell is ongoingGettyHis current Barstool Sports role has kept him active in the media landscape.The Super Bowl champion’s challenge will now be finding a network willing to take a chance on him.Stay up to date with the NFL across all our talkSPORT platforms – subscribe to our YouTube channel for the latest news, opinion, exclusive interviews and our daily unfiltered, unscripted show ‘The S* Word, from 8am ET