College coaching (1986–1991) After graduating from the University of Dayton, Gruden was hired as a graduate assistant coach at the
University of Tennessee during the 1985–86 season. After his time with the Volunteers, Gruden spent two years as the quarterbacks coach at
Southeast Missouri State. He 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. In March 1991, Gruden became the wide receivers coach for the
University of Pittsburgh under head coach
Paul Hackett.
National Football League (1992–1997) In January 1992, at age 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. Gruden 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 (1998–2001) 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 2000 and 2001. 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 champion
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''.
Tampa Bay Buccaneers (2002–2008) tour of Iraq in July 2009, where a soldier tries on 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. According to one source, Davis detailed the trade as such: "I never liked it when teams would interfere with coaches under contract...Tampa Bay came to me and they said they wanted Gruden...I felt that I put the price tag so high that they wouldn't agree to it. And they did. Gruden is no longer our coach." Gruden signed a five-year contract with the Buccaneers worth $17.5 million. 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 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 first be surpassed in
Super Bowl XLIII by
Mike Tomlin, who previously served under Gruden as the Buccaneers' defensive backs coach, and then by
Sean McVay in
Super Bowl LVI. Gruden's mantra for the
2002 season was "Pound the Rock", a reference to commitment to the running game. 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
Warren 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) 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. in December 2006 In
2006, Gruden led the Buccaneers to a dismal 4–12 season, which was his worst record as a head coach. That 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 discussed the state of the Buccaneers. During the interview, 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 Buccaneers returned to the playoffs in 2007 with a 9–7 record, including five divisional wins (after resting starters for the final two games) and 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". The Buccaneers saw their season end in the
Wild Card Round to the eventual Super Bowl XLII champion
New York Giants. In
2008, Gruden was rewarded with a contract extension through the
2011 season. 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.
Post–Tampa Bay career In May 2010, Gruden became 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 (FFCA). The organization (a "football think-tank") had its headquarters in a rented office in a Tampa strip mall. 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. 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.
Oakland / Las Vegas Raiders (2018–2021) After nine years away from coaching in the NFL, the Raiders announced the return of Gruden as head coach on January 6, 2018. He 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. 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. 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." He added: "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, ''Shit. I'm wasting my time. I got to go compete."'' Some of Gruden's 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 finished 4–12 in his first year back with the team. In 2019, due to a strong rookie class showing, Gruden led the Raiders to a 6–4 record to start the season. However, after many crucial players suffering injuries, the Raiders ended their last season in Oakland 1–5 and 7–9 overall. Gruden was fined $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. He was fined an additional $150,000 for further
COVID-19 protocol violations on November 5, 2020. Gruden led the Raiders to an 8–8 record in the 2020 season. The Raiders finished second in the AFC West with an 8-8 record and missed the playoffs. The Raiders began the
2021 season with a 3–0 record, including two overtime wins. The Raiders lost the following two games. Under their interim coach
Rich Bisaccia, the Raiders made the playoffs, something they had not done under Gruden during his second stint with the team.
Email controversy and resignation In October 2021, a league investigation into the
Washington Football Team for workplace misconduct uncovered emails Gruden sent from 2011 to 2018 to then Washington
general manager Bruce Allen where Gruden used racist, misogynistic, and homophobic slurs. The emails referred to NFL commissioner
Roger Goodell as a "
faggot", and a "clueless anti football
pussy". Gruden also said Goodell should not have pressured the Rams to draft "
queers", referring to
Michael Sam, the
first openly gay player drafted in NFL history.
Jeff Fisher, who was the coach of the Rams at the time, denied that he was pressured and stated he drafted Sam entirely based on his football skills. Gruden stated that players who
protest the national anthem should be "fired", specifically referring to former 49ers safety
Eric Reid. Gruden used a racist stereotype to describe NFLPA executive director
DeMaurice Smith, saying "Dumboriss Smith has lips the size of
michellin tires". Gruden also criticized
Barack Obama during his 2012 re-election campaign and called then–Vice President
Joe Biden a "nervous clueless pussy". Gruden also joked to Allen that he should tell
Bryan Glazer, co-owner of the Buccaneers, to perform oral sex on Gruden, and mocked
Caitlyn Jenner for receiving an ESPN award following her gender transition. Gruden announced his intentions to sue the NFL and Roger Goodell for exposing his scandals. A Nevada judge threw out a bid from the NFL to dismiss the case on May 25, 2022. Gruden was removed from the
Buccaneers Ring of Honor, where he had been inducted in 2017, as a result of the content of the emails. However, in February 2025, the Buccaneers announced Gruden would be reinstated onto the Ring of Honor.
New Orleans Saints (2023) Gruden was invited by
New Orleans Saints head coach
Dennis Allen to attend offseason meetings in May 2023 to help the offensive coaching staff adjust to new Saints quarterback
Derek Carr, but did not join as a full-time member of the staff, himself. Gruden was spotted with the Saints training camp in August 2023 and was expected to continue his advisory role.
Milano Seamen (2024) In March 2024, it was announced that Gruden had joined the
Milano Seamen of the
European League of Football as an advisor.
Hula Bowl (2026) Gruden was one of the two head coaches at the 2026
Hula Bowl. The other coach was his brother,
Jay Gruden. The event was also known as the "Gruden Bowl." A documentary on the Gruden Bowl/2026 Hula Bowl was released on January 30, 2026. ==Broadcasting and media career==