Jon Gruden

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.[8] After his time with the Volunteers, 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. Walt Harris was the offensive coordinator at Tennessee, where Gruden was one of his graduate assistant coaches, and later hired him at Pacific. In 1990, Gruden was a special assistant with the San Francisco 49ers under quarterbacks coach Mike Holmgren.[9][10] In March 1991, Gruden became the wide receivers coach for the University of Pittsburgh under head coach Paul Hackett.[11]

In January 1992, at the age of 28, Gruden was hired by Mike Holmgren, his former boss at the San Francisco 49ers, to be the special offensive assistant/wide receivers coach with the Green Bay Packers.[10] 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.

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 they made the playoffs in three consecutive 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 successful season 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 champions Baltimore Ravens. In 2001, the Raiders would return to the postseason with a 10–6 record, but in the AFC Divisional Round a negated fumble proved costly as they were defeated, 16–13, in overtime by the eventual Super Bowl champions New England Patriots. 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 slasher movie Child's Play.[12][13]

Gruden visited U.S. troops in Iraq during a USO tour in July 2009, where he allowed a serviceman to wear his Super Bowl ring.

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.[14] The trade took place for a number of reasons, including Davis's 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's 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.[14]

The Buccaneers' search for a head coach had taken more than two months, and 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 fact that the coach who the Buccaneers wanted had 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 Buccaneers 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 Buccaneers to give up as much as they did to acquire Gruden.

Immediately after arriving in Tampa Bay, 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 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 Buccaneers. Gruden, for his part, publicly and graciously thanked Dungy for his contributions upon accepting the Lombardi Trophy at the Super Bowl XXXVII postgame ceremony.

The victory made Gruden the youngest head coach to win the Super Bowl at age 39. This record would be surpassed in Super Bowl XLIII by Mike Tomlin, who previously served under Gruden as the Buccaneers' defensive backs coach.

Gruden's mantra for the 2002 season was "Pound the Rock", a reference to commitment to the running game. Gruden even went as far as to display a large chunk of granite in the locker room, a tactic mimicked by the Jacksonville Jaguars. (The Jaguars' slogan, "Keep choppin' wood", was tainted though 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.

Unable to afford replacements, the following season saw the team decimated by injuries to many of the Super Bowl stars, including Joe Jurevicius, Greg Spires, Shelton Quarles, and Brian Kelly, as well as acrimony with highly paid veterans such as Sapp and wide receivers Keyshawn Johnson and Keenan McCardell. The Buccaneers finished 7–9 in 2003 and 5–11 in 2004 to become the first team to have consecutive losing seasons after winning the Super Bowl. A particular low point during this period occurred in a Monday Night Football home matchup against the Indianapolis Colts, led by Gruden's predecessor Dungy. The Buccaneers dominated much of the game, allowing them to take a 35–14 lead near the end of the fourth quarter, but were overcome by a Colts rally that resulted in them losing 38–35.

When former Raiders general manager Bruce Allen joined the Buccaneers 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)[15] 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 Buccaneers 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 Bay and eliminate the Buccaneers from the wild-card round of the playoffs.

Gruden speaking to an official at Heinz Field in December 2006

In 2006, Gruden led the Buccaneers to a dismal 4–12 season, which was his worst record as a head coach. The 2006 season was 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 discussed the state of the Buccaneers. 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."[16]

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 Buccaneers returned to the playoffs in 2007 with a 9–7 record, including five divisional wins (after resting starters for the final two games). This 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".[17]

In 2008, Gruden was rewarded with a contract extension through the 2011 season. On November 30, Gruden earned his 100th career victory, which came 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 Gruden was fired by the Buccaneers on January 16, 2009, after seven seasons with the team.[18][19]

In May 2010, Gruden became a volunteer assistant offensive line coach at Carrollwood Day School in Tampa, Florida.[20] Shortly after being fired from Tampa Bay, Gruden created the Fired Football Coaches Association.[21] The organization (a "football think-tank") had its headquarters in a rented office in a Tampa strip mall.[22] The FFCA was known to have a large amount of game and player film collected by Gruden as well as playbooks and Gruden was known to have game plans of his own that he kept updated over the years he was not actively coaching. Many coaches such as Chip Kelly, Urban Meyer, Jim Haslett, Rick Venturi, Sean McVay, Greg Schiano and Monte Kiffin and many players came to the facility to watch film and talk with Gruden.[23] Gruden closed the FFCA upon his returning to coaching in 2018 moving the game and player film along with the other information he held there to Oakland.[24]

After nine years away from coaching in the NFL, the Raiders announced the return of Gruden as head coach on January 6, 2018.[25] Gruden signed a 10-year, $100 million contract, one of the biggest contracts in the history of the league which also includes a no-trade clause, closing the loophole that saw the Raiders trade him to the Buccaneers in return for draft picks and cash.[26] Gruden came back to coaching after six years of attempts by Raiders owner Mark Davis to lure him back to be the Raiders head coach.[27] Gruden said that he came back due to his need to go compete "I got tired of sitting in a dark room, watching tape by myself," Gruden says. "I took rumba-dancing classes; that didn’t last—I wasn’t any good. Bought a boat; I never used it. Live on a golf course; I never play. I’d go to the FFCA early, and next thing I know it’s 10:30 at night. I’m thinking, S---. I’m wasting my time. I got to go compete."[28] Some of his first few moves included signing several veterans, drafting Kolton Miller in the first round of the 2018 draft and trading away Khalil Mack for 2019 and 2020 first round draft picks, and later trading Amari Cooper for the Dallas Cowboys' first round draft pick. The team would go 4–12 in his first year back with the team. The following year, due to a strong rookie class showing, Gruden led the Raiders to a 6–4 record. However, after many crucial players suffering injuries, the Raiders would end their last season in Oakland 1-5 and 7-9 overall.

Gruden was fined US$100,000 by the NFL for not properly wearing a face mask, as required for coaches during the COVID-19 pandemic, during a week 2 game in the 2020 NFL season on September 22, 2020.[29] He was fined an additional US$150,000 for further COVID-19 protocol violations on November 5, 2020.[30]