Jon Gruden

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Coaching career

Gruden was recruited as a graduate assistant coach at the University of Tennessee in 1985-1986, after graduating from Dayton. He spent two years as the quarterbacks coach at Southeast Missouri State after his time with the Volunteers. Gruden was appointed offensive assistant as the tight ends coach at the University of the Pacific in 1989. Walt Harris was the offensive coordinator at Tennessee, where Gruden was one of his graduate assistant coaches, and he later hired him at Pacific. Gruden was a special assistant with the San Francisco 49ers under quarterback Mike Holmgren in 1990. Gruden, under head coach Paul Hackett, became the wide receivers coach for the University of Pittsburgh in March 1991.

Gruden was hired by Mike Holmgren, his former manager at the San Francisco 49ers, to be the special offensive assistant/wide receivers coach with the Green Bay Packers in January 1992 at the age of 28. Gruden, the Philadelphia Eagles' offensive coordinator, after three seasons in Green Bay, was hired as the Philadelphia Eagles' offensive coordinator under former Packers assistant coach Ray Rhodes. Gruden was then selected by the Oakland Raiders' general manager Al Davis to be the Oakland Raiders' new head coach for the 1998 season.

The Raiders won eight seasons in 1998 and 1999 under Gruden, and they then leapt out of last place in the AFC West. Gruden led the Raiders to the top of the AFC West in three seasons from 2000 to 2002 (the third season was under head coach Bill Callahan). Oakland finished 12-4 in the 2000 season, the team's most profitable season in a decade and its first division championship since 1990, eventually losing 16–3 to the eventual Super Bowl champions, the Baltimore Ravens. The Raiders would return to the playoffs in 2001 with a ten-ten record, but a negated fumble in the AFC Divisional Round proved costly, defeating the eventual Super Bowl champions New England Patriots 16–13. Gruden was with the Raiders for six years, but he picked up the coach's nickname "Chucky" from Raiders defensive lineman Grady Jackson, who said that the coach looked like the fictional character "Chucky" in the 1988 slasher film Child's Play.

Gruden traded in Tampa Bay's 2002 and 2003 first-round draft picks, 2002 and 2004 second-round draft picks, compiling a 40–28 win-loss record (including playoffs) in four seasons with the Oakland Buccaneers, worth $8 million in cash. Davis's request for a more vertical passing assault than Gruden's horizontal pass assault, the fact that Gruden's deal came to an end a year after the trade, and Davis' ambiguity about whether Gruden was worth as much money as his new one was set to pay him. Gruden has been with the Buccaneers for five years, earning him $17.5 million.

The Buccaneers' hunt for a head coach had taken more than two months, and Tampa Bay had expressed an interest in Gruden, but Davis had initially refused to release him from his service. After Parcells backed out, the team interviewed several other coaches and found that a deal was in place with Bill Parcells before Parcells resigned, apparently because of the salary cap struggles that Tampa Bay was about to face. Many fans and sports commentators began to question if the Buccaneers made the right call by dismissing Dungy, despite the franchise's ongoing search, the fact that the Buccaneers wanted had only one year remaining on his contract, and the Baltimore Colts' immediate hire of Dungy. Only a big splash hire could calm the storm, and the Buccaneers may have been motivated by this alone in acquiring Gruden.

Gruden significantly retooled the game upon landing in Tampa Bay with the addition of many free agents. Tampa's defense went to another top-ranked position as a result of the team's 12-54 record. Both the offense and defense returned to their stride in the playoffs; the Buccaneers won by 23 points per game, 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 happy with a victory over the Philadelphia Eagles in the NFC Championship game two years running, the team that had defeated Tampa Bay in the Wild Card round by a combined score of 52–12, and Gruden was especially happy with his sweeping victory over the Raiders in Super Bowl XXXVII. Despite victory in Super Bowl, there were those who attributed Gruden's victory primarily to the offense that coach Tony Dungy and defensive coordinator Monte Kiffin had arranged during Dungy's tenure with the Buccaneers. Gruden, for his part in receiving the Lombardi Trophy at the Super Bowl XXVII postgame tournament, thanked Dungy publicly and generously thanked him.

Gruden became the youngest head coach to win the Super Bowl at age 39 thanks to the victory. Mike Tomlin, the Buccaneers' defensive backs coach who previously worked under Gruden, will first be surpassed in Super Bowl XLIII, followed by Sean McVay in Super Bowl LVI.

"Pound the Rock" was Gruden's mantra for the 2002 season, a reference to his dedication to the running game. Gruden went so far as to display a large block of granite in the locker room, a Jacksonville Jaguars tactic. (When punter Chris Hanson broke his leg on an axe brought in to accompany a large log, the Jaguars' slogan, "Keep choppin' wood," was tainted.) On his return to Tampa after winning Super Bowl XXVII, he led a capacity crowd at Raymond James Stadium in chanting the word. However, it seemed that it had disappeared from the lexicon the following year, and was not widely advertised or shown on stadium video boards.

The team was decimated by injuries to several of the Super Bowl players, including Joe Jurevicius, Greg Spires, Shelton Quarles, and Brian Kelly, as well as a lawsuit against highly compensated veterans, such as Sapp and wide receiver Keyshawn Johnson and Keenan McCardell, as well as a Sapp and wide receivers. After winning the Super Bowl, the Buccaneers won 7-9 in 2003 and 5-11 in 2004 to become the first team to have consecutive losing seasons. In a Monday Night Football home matchup against the Indianapolis Colts, Gruden's predecessor Dungy was at a low point during this period. For much of the game, the Buccaneers ruled, allowing them to take a 35–14 lead near the end of the fourth quarter. However, they were defeated by Colts' revival, which culminated in them losing 38-35.

When former Buccaneers general manager Bruce Allen joined the Buccaneers in 2004, the team finally had the general manager-head coach relationship he adored, but their 2004 and 2005 drafts found only a handful of key players, including 2005 Offensive NFL Rookie of the Year Award winner Carnell "Cadillac" Williams.

Likewise, 2005 marked a return to the playoffs as the Buccaneers posted a remarkable 11-05 record, despite starting quarterback Brian Griese's absence and several controversial coaching decisions, including a two-point conversion in the final seconds to beat the Washington Redskins, who would later return to Tampa Bay and ban the Buccaneers from the wild-card round of the playoffs, including a two-point conversion.

Gruden led the Buccaneers to a humiliating 4–12 season in 2006, his lowest mark as a head coach. The 2006 season marked 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, Buccaneers executive vice president Joel Glazer addressed the Buccaneers' state. During an interview, Joel Glazer defended Gruden's results, citing failed draft picks, injuries, and salary cap questions. "Mediocrity will never be appropriate for the Buccaneers," the Buccaneers' president said, "but we must continue."

In 2007, the team finally escaped from salary cap space, and united Gruden with a mobile West Coast quarterback in former Pro Bowler and Grey Cup champion Jeff Garcia. The Buccaneers won 9–7 in 2007, with five in divisional titles (after resting starters for the final two games). Despite suffering major injuries, several seasons running, to key players such as Luke Petitgout, Carnell Williams, Alex Smith, Brian Kelly, Barrett Ruud, Patrick Chukwurah, Gaines Adams, and starting kick and punt returner Mark Jones. Despite this adversity, Gruden said, "The future is so beautiful around here, I must wear shades."

Gruden was given a job extension for the 2011 season in 2008. Gruden won his 100th game in his career against the New Orleans Saints on November 30, his 100th victory in his career. The Buccaneers were on target to make the playoffs, boasting a bye week and having home field advantage going into December. However, the Buccaneers went winless in December, in no small part because of the team's defensive demise, which resulted in the team's loss of 30.75 points per game. The Buccaneers were barred from qualifying for the playoffs by the Oakland Raiders on December 28, but the Buccaneers were drafted to Tampa Bay. Gruden was fired by the Buccaneers on January 16, 2009, after seven seasons with the Buccaneers, ending the season with four losses in a row.

Gruden began volunteering at Carrollwood Day School in Tampa, Florida, in May 2010. Gruden was fired from Tampa Bay just short of joining the Fired Football Coaches Association (FFCA). The group, which was a "football think tank"), had its headquarters in a rented office in a Tampa strip mall. Gruden's FFCA had a large amount of game and player film as well as playbooks, and Gruden had game plans that he kept updated throughout his years of teaching. Many coaches, including Chip Kelly, Urban Meyer, Jim Haslett, Rick Venturi, Sean McVay, Greg Schiano, Monte Kiffin, and many others attended the game and talked to Gruden. Gruden left the FFCA after returning to coaching in 2018 in addition to other details he held in Oakland.

The Raiders announced Gruden as the head coach on January 6, 2018. Gruden was nine years away from teaching in the NFL. Gruden signed a 10-year, $100 million deal, one of the league's longest, as well as a no-trade clause, closing the loophole that allowed the Raiders to trade him to the Buccaneers in exchange for draft picks and cash. After six years of Raiders owner Mark Davis' attempts to lure him back to be the Raiders head coach, Gruden returned to coaching. "I got sick of sitting in a dim room, watching tape by myself," Gruden said. "I took rumba-dancing lessons, but it didn't work"; I wasn't any good," he said. I never used it because it was bought a boat. I live on a golf course; I never play. I'd get to the FFCA early in the morning, but then I'd see it's 10:30 at night. Shit, I'm thinking. My time is being wasted. "I have to compete." Khalil Mack's first few moves included signing several veterans, designing Kolton Miller in the first round of the 2018 draft, and then trading Amari Cooper for the Dallas Cowboys' first-round draft pick. In his first year with the team, the team will go 4-12. Gruden led the Raiders to a 6–4 record in the following year, owing to a solid rookie class record. However, the Oakland Raiders will miss their last season in Oakland 1-5 and 7-9 overall, after a number of key players are injured.

During a week 2 game in the 2020 NFL season, Gruden was fined $100,000 by the NFL for not wearing a face mask as required for coaches during the COVID-19 pandemic. On November 5, 2020, he was fined an additional $150,000 for further COVID-19 protocol infractions.

Las Vegas opened the 2021 season with a 3–0 record, two overtime victories, and then lost in the next two games. The Raiders made the playoffs under new head coach Rich Bisaccia, something they had not do under Gruden during his second stint with the team.

Gruden sent emails to then Washington general manager Bruce Allen in October 2021, where Gruden used racist, misogynistic, and homophobic terms. The emails were written between 2011 and 2018. NFL commissioner Roger Goodell was referred to in the emails as a "faggot" and a "clueless anti-foot pussy." Goodell may not have compelled the Rams to draft "queers," referring to Michael Sam, the first openly gay player to be drafted in NFL history. Jeff Fisher, the Rams' head coach, denied being threatened and said he was not pressured to draft Sam completely based on his football abilities. Former 49ers safety Eric Reid is among those who protest the National Anthem who protest the National Anthem should be "fired," Gruden said. "Dumboriss Smith has lips the size of michellin [sic] tires," Gruden said of NFLPA executive director DeMaurice Smith. Gruden also called then US Vice President Joe Biden a "nervous clueless pussy." Gruden also joked to Allen that he should instruct Bryan Glazer, the Buccaneers' co-owner, to perform oral sex on Gruden. Unknown members of the Washington Football Team staff sent Gruden, Allen, and others emails containing topless photographs of women, including two Washington Football Team cheerleaders. After the emails were revealed by The New York Times, Gruden resigned on October 11, 2021. Gruden also stated his plans to sue the NFL and Roger Goodell for exposing his scandals. On May 25, 2022, a Nevada judge dismissed a NFL attempt to dismiss the lawsuit.

Gruden was barred from the Buccaneers Ring of Honor, where he had been inducted in 2017 because of the emails' content.

Broadcasting career

Gruden was hired by ESPN in May 2009 to appear as a color analyst on its Monday Night Football telecasts, replacing Tony Kornheiser. He also contributed to the 2010 Rose Bowl and 2011 Orange Bowl on ESPN Radio and the 2011 Orange Bowl on ESPN, as an analyst for ESPN's coverage of the NFL Draft and postseason college football games. Gruden became the subject of Jon Gruden's QB Camp, where he went over the NFL Draftees at quarterback, including Andrew Luck and Robert Griffin III, which is when he speaks about what he feels to be the best play in football (in which the fullback travels on a flat route and is the primary target). Gruden awarded the "Gruden Grinder" weekly prize to the best player in the game this week during Monday Night Football's broadcast.

Gruden signed a six-year contract extension with ESPN, which extended his time with the broadcasting company for another five years. Gruden and ESPN agreed to a contract extension through 2021 on December 15, 2014, but gave an exception in the case where he wanted to return to teaching. Gruden became ESPN's highest-paid celebrity as a result of the hire. Since deciding to return to the coaching ranks with the Oakland Browns for the 2018 NFL season, he took his last game for ESPN, the Tennessee Titans and the Kansas City Chiefs.

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