Jon Gruden Jon David Gruden ( born August 17 , 1963 ) is an NFL analyst for ESPN . Previously , he was the head coach of the NFL ' s Tampa Bay Buccaneers , the team that won Super Bowl XXXVII , defeating the Oakland Raiders , whom he had left at the end of the previous season . At the time , Gruden was the youngest head coach ever to win a Super Bowl , aged 39 years , 5 months and 9 days . Early life . Jon Gruden was born August 17 , 1963 in Sandusky , Ohio into a family having ties to football . His father Jim would later serve as a professional football regional scout and running backs coach , his brother Jay would play and coach in the Arena Football League and become an assistant professional football coach , and Gruden would go onto marry Cindy , a University of Tennessee football cheerleader , and have a long career in football . While growing up in Sandusky , Gruden was a Cleveland Browns fan and raised in the Roman Catholic faith . When he was 15 , Gruden attended Clay High School in South Bend , Indiana , during which his father Jim served as an assistant to Dan Devine at the University of Notre Dame . After graduating from high school in 1981 , Gruden attended Muskingum College in New Concord , Ohio and later transferred to the University of Dayton , where he was a three - year letterman at quarterback under coach Mike Kelly and graduated with a degree in communications in 1985 . Career . After graduating from the University of Dayton , Gruden was hired as a graduate assistant coach at the University of Tennessee during the 1985 - 1986 season . He spent two years after that as the quarterbacks coach at Southeast Missouri State . Gruden then moved to the University of the Pacific in 1989 as offensive assistant as the tight ends coach , where he coached Scott Lubow who was second team All Conference . In 1990 , Gruden was a special assistant with the San Francisco 49ers under quarterback coach Mike Holmgren . In March 1991 , Gruden became the wide receivers coach for the University of Pittsburgh under Paul Hackett . Walt Harris was the offensive coodinator at Tennessee , where Gruden was one of his graduate assistant coaches , and later hired him at Pacific . Pro coaching career . In January 1992 when he was 28 , Gruden was hired by Mike Holmgren , his former boss at the San Francisco 49ers , to be the special offensive assistant / wide receiver s coach with the Green Bay Packers . After three seasons in Green Bay , Gruden became the offensive coordinator of the Philadelphia Eagles under former Packers assistant coach Ray Rhodes . Gruden then was chosen by the owner and general manager of the Oakland Raiders , Al Davis , to be the Raiders ' new head coach for the 1998 season . Oakland Raiders . Under Gruden , the Raiders posted consecutive 8 – 8 seasons in 1998 and 1999 , and leapt out of last place in the AFC West . After uniting with journeyman quarterback Rich Gannon , Gruden led the Raiders to the top of the AFC West and made the playoffs three straight seasons ( the third time under Head Coach Bill Callahan ) . Oakland finished 12 – 4 in the 2000 season , the team ' s most successful in a decade , and its first division title since 1990 , ultimately reaching the AFC Championship , where they lost 16 – 3 to the eventual Super Bowl champion Baltimore Ravens . While Gruden was with the Raiders , Gruden acquired his nickname " Chucky " from Raiders defensive lineman Grady Jackson , who thought that the coach looked like the fictional character " Chucky " in the 1988 movie Child ' s Play . Tampa Bay Buccaneers . After compiling a 40 – 28 win - loss record ( including playoffs ) in four seasons with the Raiders , Gruden replaced the fired Tony Dungy as head coach of the Tampa Bay Buccaneers in 2002 , via a high - stakes trade that included Tampa Bay ' s 2002 and 2003 first - round draft picks , 2002 and 2004 second - round draft picks , and $ 8 million in cash . The trade took place for a number of reasons , including Davis ' desire for a more vertical passing attack rather than Gruden ' s horizontal pass attack , the fact that Gruden ' s contract would expire a year after the trade , and Davis ' uncertainty over whether Gruden was worth as much money as his next contract was sure to pay him . Gruden signed a five - year contract with the Buccaneers worth $ 17 . 5 million . The Bucs ' search had taken more than two months , and had proven to be a major embarrassment to the Buccaneer organization . Tampa Bay had expressed an interest in Gruden , but Davis had originally refused to release him from his contract . The team subsequently interviewed several other coaches and believed a deal was in place with Bill Parcells , before Parcells backed out , reportedly because his choice for General Manager , Mike Tannenbaum , told him not to accept the job because of the salary cap difficulties that Tampa Bay was about to endure . With the franchise ' s search floundering , the coach they wanted having only one year remaining on his deal , and the immediate hire of Dungy by the Indianapolis Colts , many fans and sports commentators began to openly question if the Bucs had made the right move by dismissing Dungy . Only a big splash hire could quiet the storm , and this may have been the primary motivation for the Bucs to give up as much as they did to acquire Gruden . Immediately after arriving in Tampa , Gruden significantly retooled the offense with the addition of numerous free agents . His determination to fix the under - performing offense so often maligned during Dungy ' s tenure inspired Tampa ' s defense to another # 1 ranking , which helped the team to a 12 – 4 season . Both the offense and defense hit their stride in the playoffs ; the Buccaneers posted a playoff per - game point differential of 23 points per game in victory , tied with the 1992 Dallas Cowboys for the highest average playoff margin of victory by a Super Bowl winner in the free agency era . Fans were especially satisfied with a victory in the NFC Championship game against the Philadelphia Eagles , the team that had defeated Tampa Bay in the Wild Card round two years running by the combined score of 52 - 12 , and Gruden was especially satisfied with a dominant win over his old team , the Raiders , in Super Bowl XXXVII . Despite the Super Bowl win , there were many , including players on the Buccaneers like Warren Sapp , who attributed Gruden ' s win primarily to the defense that coach Tony Dungy and defensive coordinator Monte Kiffin had created during Dungy ' s tenure with the Bucs . Gruden , for his part , publicly and graciously thanked Dungy for his contributions upon accepting the Lombardi Trophy at the Super Bowl XXXVII postgame ceremony . His mantra for the 2002 season was " Pound the Rock " , a reference to never giving up . Gruden even went as far as to display a large chunk of granite in the locker room , a tactic mimicked by the Jacksonville Jaguars . ( Their slogan , " Keep choppin ' wood " , was tainted when punter Chris Hanson injured his leg on an axe brought in to accompany a large log . ) Upon returning to Tampa after winning Super Bowl XXXVII , he led a capacity crowd at Raymond James Stadium in chanting the phrase . However , it seemingly disappeared from the lexicon the following year , and was not aggressively marketed or displayed on stadium video boards . In the two years following Gruden ' s Super Bowl win , the Bucs went 7 – 9 and 5 – 11 respectively , implying to many Dungy supporters that Gruden had simply taken over a strong team and driven it into the ground . However , the high draft picks sacrificed by the team to acquire Gruden , along with salary - cap issues and failed draft choices forced upon him by the now - departed Rich McKay ( with whom Gruden had a bitter relationship ) limited Gruden ' s ability to field the teams he wanted after that successful Super Bowl - winning season . With no emerging talent in the fold and no money to afford replacements , the team was decimated by injuries to many of the Super Bowl stars , including Joe Jurevicius , Greg Spires , Shelton Quarles , and ( cornerback ) , as well as acrimony with highly - paid veterans such as Sapp , Keyshawn Johnson and Keenan McCardell . When former Raiders general manager Bruce Allen joined the Bucs in 2004 , Gruden finally had the general manager – head coach partnership he desired , and while the salary cap continued to plague the team ( which spent the least money in the league between 2004 and 2009 ) their 2004 and 2005 drafts yielded a few impact players , including 2005 Offensive NFL Rookie of the Year Award winner Carnell " Cadillac " Williams . Also , 2005 marked a return to the playoffs , as the Bucs ' posted a surprising 11 – 5 record , despite the loss of starting quarterback Brian Griese and some controversial coaching decisions , including a two - point conversion in the final seconds to defeat the Washington Redskins , who would later return to Tampa and eliminate the Bucs from the wild - card round of the playoffs . In 2006 , Gruden led the Buccaneers to a 4 – 12 season . It was his worst record as a head coach and the first time a Tampa Bay team had not won more than four games since 1991 . In an interview with Ira Kaufman of " The Tampa Tribune " on March 28 , 2007 , Bucs executive vice president Joel Glazer discussed the state of the Bucs . During the interview , Joel Glazer defended Gruden ' s performance , citing lost draft picks , injuries , and salary cap issues . However , he also said " Mediocrity will never be standard for the Buccaneers , but we have to move on . " In 2007 , the team finally cleared itself of salary cap constraints and united Gruden with a mobile West Coast quarterback in former Pro Bowler and Grey Cup winner Jeff Garcia . The team posted a 9 – 7 record with five division wins ( after resting starters for the final two games ) , despite suffering major injuries , several season - ending , to critical players like Luke Petitgout , Carnell Williams , Mike Alstott , Alex Smith , Brian Kelly , Barrett Ruud , Michael Clayton , Patrick Chukwurah , Gaines Adams and starting kick and punt returner Mark Jones . Despite this adversity , however , Gruden declared " The future is so bright around here I have to wear shades " . In 2008 , Gruden was rewarded with a contract extension through the 2011 season . On November 30 , Gruden earned his 100th win , against the New Orleans Saints . Going into December the Buccaneers were on pace to make the playoffs , claim a bye week and have home field advantage . However , the Buccaneers went winless in the month of December , in no small part due to a defensive collapse that saw the team give up an average of 30 . 75 points per game . On December 28 the Buccaneers were eliminated from making the playoffs by the Oakland Raiders , the team Gruden left for Tampa Bay . The Buccaneers ended the season with four losses in a row , and Jon Gruden was fired by the Buccaneers on January 16 , 2009 , after seven seasons with the team . Post – Tampa Bay career . Jon Gruden is now a volunteer assistant offensive line coach at Carrollwood Day School in Tampa , Florida . Shortly after being fired from Tampa Bay , Gruden created the Fired Football Coaches Association . The club ' s headquarters is in a rented office in a Tampa strip mall . Broadcasting . In May 2009 , Gruden was hired by ESPN to serve as a color analyst on its " Monday Night Football " telecasts , replacing Tony Kornheiser . He has also served as an analyst for ESPN ' s coverage of postseason college football games , helping to call the 2010 Rose Bowl and 2010 BCS National Championship Game on ESPN Radio and the 2011 Outback Bowl and 2011 Orange Bowl on ESPN television , and in the spring of 2012 was the focus of the series " Jon Gruden ' s QB Camp " , where Gruden went over the NFL development process with prospective NFL draft ees at quarterback , including Andrew Luck and Robert Griffin III . He has recently signed a contract extension with ESPN , beginning in September 2012 , which will lengthen his tenure with the broadcasting company for another five years . Coaching tree . NFL head coaches under whom Jon Gruden has served : Assistant coaches under Jon Gruden who have become NFL head coaches : Personal life . Gruden is a Roman Catholic . He and his wife , Cindy , have three sons , Jon II ( Deuce ) , Michael , and Jayson . Gruden ' s younger brother Jay is currently the offensive coordinator of the Cincinnati Bengals . Jon ' s wife Cindy is from East Tennessee and graduated from the University of Tennessee , where Gruden also coached briefly in 1986 . References . Gruden was last seen on WWE Monday Night Raw Episode January 7 2013 .