Career Timeline of Jon Gruden: Major Achievements and Milestones

How Jon Gruden built a successful career. Explore key moments that defined the journey.

Jon Gruden is a former American football coach and media personality. He achieved significant success as the head coach of the Oakland Raiders (1998-2001, 2018-2021) and Tampa Bay Buccaneers (2002-2008), leading the Buccaneers to a Super Bowl XXXVII victory. Gruden also had a prominent career as a color commentator for ESPN's Monday Night Football. His coaching career ended abruptly in 2021 after emails containing racist, misogynistic, and homophobic remarks surfaced, leading to his resignation from the Raiders. He is currently employed by Barstool Sports.

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Full Timeline Career & Achievements

1985: Graduate Assistant Coach at University of Tennessee

In 1985, Jon Gruden was hired as a graduate assistant coach at the University of Tennessee.

1989: Offensive Assistant at University of the Pacific

In 1989, Jon Gruden became an offensive assistant and tight ends coach at the University of the Pacific.

1990: Special Assistant with the San Francisco 49ers

In 1990, Jon Gruden was a special assistant with the San Francisco 49ers, working under quarterbacks coach Mike Holmgren.

1990: Raiders First Division Title

In 2000, the Oakland Raiders won their first division title since 1990.

March 1991: Becomes Wide Receivers Coach at University of Pittsburgh

In March 1991, Jon Gruden became the wide receivers coach for the University of Pittsburgh under head coach Paul Hackett.

January 1992: Hired by Green Bay Packers

In January 1992, Jon 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.

1998: Became Raiders Head Coach

In 1998, Jon Gruden became the head coach of the Oakland Raiders.

1998: Named Head Coach of the Oakland Raiders

In 1998, Jon Gruden was chosen by Al Davis, the owner and general manager of the Oakland Raiders, to be the Raiders' new head coach.

1998: Raiders Post 8-8 Season

In 1998, under Jon Gruden, the Oakland Raiders posted an 8-8 season record.

1999: Raiders Post 8-8 Season

In 1999, under Jon Gruden, the Oakland Raiders posted another 8-8 season record.

2000: Raiders Reach AFC Championship

In the 2000 season, Jon Gruden led the Oakland Raiders to the AFC Championship after finishing with a 12-4 record and winning their first division title since 1990.

2001: AFC Championship Appearance

In 2001, Jon Gruden coached the Oakland Raiders, leading them to an AFC Championship Game appearance.

2001: Raiders Return to Postseason

In 2001, the Oakland Raiders returned to the postseason with a 10-6 record under Jon Gruden.

2002: Hired as Buccaneers Head Coach

In 2002, Jon Gruden was hired as the head coach of the Tampa Bay Buccaneers, replacing Tony Dungy.

2002: Traded to Tampa Bay Buccaneers

In 2002, Jon Gruden was traded to the Tampa Bay Buccaneers from the Oakland Raiders. He subsequently led the Buccaneers to their first Super Bowl title in Super Bowl XXXVII the same season.

2003: Draft Pick Trade with Raiders

In 2003, the Tampa Bay Buccaneers traded their first-round draft pick to the Raiders as part of the compensation for acquiring Jon Gruden in 2002.

2004: Bruce Allen Joins Buccaneers

In 2004, Bruce Allen joined the Tampa Bay Buccaneers as general manager, forming the partnership that Jon Gruden desired.

2004: Draft Pick Trade with Raiders

In 2004, the Tampa Bay Buccaneers traded their second-round draft pick to the Raiders as part of the compensation for acquiring Jon Gruden in 2002.

2005: Buccaneers Return to Playoffs

In 2005, the Tampa Bay Buccaneers posted an 11-5 record, returning to the playoffs, despite injuries and controversial coaching decisions.

2006: Dismal Season for Buccaneers

In 2006, Jon Gruden led the Buccaneers to a 4-12 season, which was his worst record as a head coach.

March 28, 2007: Joel Glazer Defends Gruden

On March 28, 2007, Buccaneers executive vice president Joel Glazer defended Jon Gruden's performance, citing lost draft picks, injuries, and salary cap issues.

2007: Buccaneers Return to Playoffs

In 2007, the Tampa Bay Buccaneers returned to the playoffs with a 9-7 record, despite significant injuries to key players. Jon Gruden declared "The future is so bright around here I have to wear shades".

2008: Contract Extension Through 2011

In 2008, Jon Gruden was rewarded with a contract extension through the 2011 season. The Buccaneers collapsed in December, failing to make the playoffs.

2008: End of Tenure with Buccaneers

In 2008, Jon Gruden's tenure as head coach of the Tampa Bay Buccaneers came to an end, after setting the franchise record for wins, but only making two further playoff runs.

January 16, 2009: Gruden Fired by Buccaneers

On January 16, 2009, Jon Gruden was fired by the Tampa Bay Buccaneers after seven seasons with the team.

May 2009: Gruden Hired by ESPN

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

2009: Joins ESPN's Monday Night Football

In 2009, Jon Gruden became an analyst for ESPN's "Monday Night Football" broadcasts.

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May 2010: Volunteer Assistant Offensive Line Coach

In May 2010, Jon Gruden became a volunteer assistant offensive line coach at Carrollwood Day School in Tampa, Florida.

2010: Analyst for College Football Games

In 2010, Jon Gruden served as an analyst for ESPN's coverage of the NFL draft and postseason college football games, helping to call the 2010 Rose Bowl and 2010 BCS National Championship Game on ESPN Radio.

2011: Gruden's Contract Extension

In 2008, Jon Gruden was rewarded with a contract extension through the 2011 season with the Buccaneers.

2011: Analyst for College Football Games

In 2011, Jon Gruden served as an analyst for ESPN's coverage of the NFL draft and postseason college football games, helping to call the 2011 Outback Bowl and 2011 Orange Bowl on ESPN.

September 2012: Contract Extension with ESPN

In September 2012, Jon Gruden signed a contract extension with ESPN, lengthening his tenure with the broadcasting company for another five years.

2012: Jon Gruden's QB Camp Series

In the spring of 2012, Jon Gruden became the focus of the series Jon Gruden's QB Camp, where he went over the NFL development process with prospective NFL draftees at quarterback, including Andrew Luck and Robert Griffin III.

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December 15, 2014: Further Contract Extension with ESPN

On December 15, 2014, Jon Gruden and ESPN agreed to a contract extension through 2021, allowing an opt-out in the event he wanted to return to coaching.

2017: Final Season on ESPN's Monday Night Football

2017 was Jon Gruden's final season as an analyst for ESPN's "Monday Night Football" broadcasts.

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2017: Departure from ESPN

In 2018, after deciding to return to the coaching ranks with the Raiders, Jon Gruden's last game for ESPN was the 2017 AFC Wild Card Round between the Tennessee Titans and the Kansas City Chiefs.

January 6, 2018: Gruden Returns to the Raiders as Head Coach

On January 6, 2018, the Raiders announced Jon Gruden's return as head coach, signing him to a 10-year, $100 million contract with a no-trade clause. This marked his return after six years of attempts by Raiders owner Mark Davis to lure him back.

2018: Closes FFCA and Returns to Coaching

In 2018, Jon Gruden closed the Fired Football Coaches Association (FFCA) upon his return to coaching, moving its assets to Oakland.

2018: Returns to Raiders as Head Coach

In 2018, Jon Gruden returned to the Raiders as their head coach.

2018: Departure from ESPN

In 2018, after deciding to return to the coaching ranks with the Raiders, Jon Gruden's last game for ESPN was the 2017 AFC Wild Card Round between the Tennessee Titans and the Kansas City Chiefs.

2019: Raiders' 2019 Season

In 2019, Jon Gruden led the Raiders to a 6–4 record to start the season, thanks to a strong rookie class. However, due to injuries to crucial players, the Raiders finished the season with a 1–5 record, ending 7–9 overall.

October 11, 2021: Gruden Resigns

On October 11, 2021, Jon Gruden resigned after details of his emails were released by The New York Times. Gruden announced his intentions to sue the NFL and Roger Goodell.

2021: Resignation from Raiders

In 2021, Jon Gruden resigned as head coach of the Raiders after it was publicly revealed that he wrote and sent many racist, misogynistic, and homophobic emails between 2011 and 2018.

2021: Raiders' 2021 Season

In 2021, the Raiders began the season with a 3-0 record, but lost the following two games. The Raiders made the playoffs under interim coach Rich Bisaccia, something they had not done under Jon Gruden during his second stint with the team.

2021: Contract Extension with ESPN

On December 15, 2014, Jon Gruden and ESPN agreed to a contract extension through 2021, allowing an opt-out in the event he wanted to return to coaching.

May 2023: Gruden Invited to Saints' Offseason Meetings

In May 2023, Jon Gruden was invited by New Orleans Saints head coach Dennis Allen to attend offseason meetings to help the offensive coaching staff adjust to new Saints quarterback Derek Carr.

August 2023: Gruden Spotted at Saints Training Camp

In August 2023, Jon Gruden was spotted with the Saints training camp and was expected to continue his advisory role.

2023: Saints Offensive Coaching Workout

In 2023, Jon Gruden was brought in by the Saints for a work-out for their offensive coaching.

March 2024: Gruden Joins Milano Seamen as Advisor

In March 2024, it was announced that Jon Gruden had joined the Milano Seamen of the European League of Football as an advisor.

November 2024: Gruden Joins Barstool Sports

In November 2024, Jon Gruden joined Barstool Sports and is featured on shows such as The Pro Football Football Show, the Shred Line, and Gruden's QB Class.

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