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 an American former football coach. He achieved success as the head coach of the Oakland Raiders and Tampa Bay Buccaneers, winning Super Bowl XXXVII with the Buccaneers. Gruden later became a prominent football analyst for ESPN's Monday Night Football. He returned to coaching with the Raiders in 2018, signing a 10-year contract, but resigned in 2021 after emails containing racist, homophobic, and misogynistic remarks surfaced. He is currently employed by Barstool Sports.

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Full Timeline Career & Achievements

May 2009: Gruden Joins ESPN

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

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2010: Gruden calls the 2010 Rose Bowl and BCS National Championship on ESPN Radio

In 2010, Jon Gruden helped cover the 2010 Rose Bowl and 2010 BCS National Championship Game on ESPN Radio.

2011: Gruden calls the 2011 Outback Bowl and Orange Bowl on ESPN

In 2011, Jon Gruden was an analyst for ESPN's coverage of the 2011 Outback Bowl and 2011 Orange Bowl.

September 2012: Gruden Signs ESPN Contract Extension

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

2012: Gruden stars in Jon Gruden's QB Camp

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: Gruden and ESPN Agree to Contract Extension

On December 15, 2014, Jon Gruden and ESPN agreed to a contract extension through 2021 that allowed an opt-out if he wanted to return to coaching, making him the highest paid personality at ESPN.

2017: Gruden's Last Game for ESPN

In 2017, 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: Raiders Announce Gruden's Return

On January 6, 2018, the Raiders announced Jon Gruden's return as head coach with a 10-year, $100 million contract, which included a no-trade clause.

2018: Gruden Returns to Coaching

In 2018, Jon Gruden decided to return to the coaching ranks with the Raiders for the 2018 NFL season.

October 11, 2021: Gruden Resigns from Raiders

On October 11, 2021, Jon Gruden resigned as head coach of the Las Vegas Raiders after details of his emails containing racist, misogynistic, and homophobic slurs were released by The New York Times.

May 2023: Gruden Invited to Saints 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.

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, featuring on shows such as The Pro Football Football Show, the Shred Line, and Gruden's QB Class.