In January 2003, Jon Gruden walked into the Philadelphia Eagles’ Veterans Stadium, where he once drew up plays as the Eagles’ young offensive coordinator, and sent the Eagles home with a 27-10 NFC Championship loss. It was the last game ever played at the Vet.
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But when Gruden looks back on his career, the moment he calls ‘the most disappointing thing’ isn’t a loss or a firing. It’s what happened in Philadelphia between 1995 and 1997.
During a recent conversation on his Family Football Show, Gruden revealed what his time with the Eagles was like.
“I was offensive coordinator for the Eagles in 1995. I was 31 years old. I was brought in to coach Randall Cunningham and put him into the West Coast offense,” Gruden recalled. “It didn’t work out. Randall was in a different space in his career. He didn’t really fit the West Coast offense. And it was the most disappointing thing in my career ’cause I love Randall.”
“He was such a friend to me and such a nice guy. He bought me suits. He was my friend, man. And we were working hard to put this offense together, but it didn’t work out.”
Gruden’s regret stems not from the offensive failure itself, but from his inability to help a friend and mentor adjust to a new system.
Before joining the Eagles as the offensive coordinator in 1995, Gruden had accumulated nine years of coaching experience across both the collegiate and NFL levels, starting from Graduate Assistant at Tennessee Volunteers to Wide receivers coach at the Green Bay Packers.
At age 31, these qualifications made him the youngest offensive coordinator in the NFL at the time. Hired by first-time head coach Ray Rhodes, Gruden was brought in to revive Philadelphia’s stagnant attack by installing a West Coast offense that uses short, high-percentage passes to stretch the defense horizontally instead of relying on traditional deep throws and heavy running plays.
Having learned under Mike Holmgren at the San Francisco 49ers and George Seifert at the Packers, Gruden was expected to elevate the Eagles with his offense, especially quarterback Randall Cunningham.
However, Gruden’s time in Philly turned out quite the opposite of those expectations. He felt the team couldn’t adjust to the West Coast style of offense. So in three years, he recorded a 26-21-1 regular-season record and a 1-2 playoff record across two postseason appearances.
Gruden then left the Eagles in January 1998 after taking the job of head coach at the Oakland Raiders. His time with the Eagles did not end on a sour note; he accepted a major career promotion. At age 34, he became the youngest head coach in the NFL at the time.
From then on, Gruden continued his NFL career as the head coach of the Oakland, now Las Vegas Raiders (1998-2001, 2018-2021) and then the Tampa Bay Buccaneers (2002-2008). He collected several honors along the way, including winning the Super Bowl XXXVII with the Buccaneers.
However, Gruden has actually stepped away from full-time NFL coaching twice in his career to take on other roles, first voluntarily, to move into broadcasting in 2009, and most recently in October 2021, when he resigned from the Raiders.
As things stand, it has been years since Gruden’s tenure with the Eagles ended. He currently works full-time as a sports media personality for Barstool Sports.