He held his first head coaching position with the Raiders franchise during their Oakland tenure from 1998 to 2001, where he won two consecutive division titles and made an AFC Championship Game appearance.

[4] His father, Jim, later served as a professional football regional scout, quarterbacks coach, and director of player personnel for the Tampa Bay Buccaneers.

[7] At the age of 15, he attended Clay High School in South Bend, Indiana, home to the University of Notre Dame, where his father served as an assistant to head coach Dan Devine.

[13] 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.

[12] After three seasons in Green Bay, Gruden became the offensive coordinator of the Philadelphia Eagles under former Packers assistant coach Ray Rhodes.

[17][18] 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.

[19][20] 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.

[25][26] 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.

[25] 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.

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.

[36] Gruden, for his part, publicly and graciously thanked Dungy for his contributions upon accepting the Lombardi Trophy at the Super Bowl XXXVII postgame ceremony.

[40][41] Upon returning to Tampa after winning Super Bowl XXXVII, he led a capacity crowd at Raymond James Stadium in chanting the phrase.

[citation needed] 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.

[42][43][44] 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.

[45] 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)[46][47] their 2004 and 2005 drafts yielded a few impact players, including 2005 Offensive NFL Rookie of the Year Award winner Carnell "Cadillac" Williams.

[48][49] 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.

During the interview, Glazer defended Gruden's performance, citing lost draft picks, injuries, and salary cap issues.

"[56] 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)[57] 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.

[58] The Buccaneers saw their season end in the Wild Card Round to the eventual Super Bowl XLII champion New York Giants.

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.

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.

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.

[89] Gruden also criticized Barack Obama during his 2012 re-election campaign and called then–Vice President Joe Biden a "nervous clueless pussy".

[97] In May 2009, Gruden was hired by ESPN to serve as a color analyst on its Monday Night Football telecasts, replacing Tony Kornheiser.