When Jon Gruden became the youngest offensive coordinator in the NFL, he had the job of designing plays for a quarterback 5 months older than him: Philadelphia Eagles’ Randall Cunningham. Under first-year head coach Ray Rhodes, Gruden brought an infectious enthusiasm to the job that the organization appreciated. But looking back at that stint, Gruden has some regrets.

On the latest edition of The Originals with Suzy Kolber, the host asked if he could have allowed himself some “grace” for the limited ball knowledge he had at the time. Gruden agreed, but on the same breath, noted Coach Rhodes should have gone another way.

“Yeah, I obviously can. I could say, ‘Well, I was just a young scrapper back then,’” Gruden said. “But maybe I shouldn’t have got the job. Maybe Ray Rhodes shouldn’t have hired me because he inherited Randall Cunningham. That’s why this profession is – it’s crazy to see 10 head coaches, 20 offensive coordinators replaced. It seems like it’s every year.”

Even with all the enthusiasm Jon Gruden brought to the team in 1995, he and Rhodes couldn’t get the offense going. Injuries and missed time were consistent with Cunningham, leaving the Eagles scrambling for answers. While Cunningham played only seven games that season (starting 4), the Eagles still managed a 10-6 record, reached the playoffs, and lost in the divisional round.

Cunningham – being benched behind Rodney Peete, felt unhappy in his diminished role, and retired from football after that campaign. Rhodes and Gruden had found success, though, and they kept their jobs. Nobody signed Cunningham in ‘96, and he finally got another chance with the Minnesota Vikings in ‘97.

Now, Gruden had spent a year with the San Francisco 49ers (1990) as an offensive assistant – a stint that shaped a lot of his early offensive philosophies and also impacted his time with the Eagles. While speaking to Kolber, Gruden revealed how the Niners created their system, and how he differs from that old philosophy now.

“We used to have a library in San Francisco where Bill Walsh would keep all of his game plans over the years,” Gruden said. “They were protective of their system. That 49ers system – it was very exclusive to them. Now, I kind of look at football like, ‘Who gives a sh*t? You know, let’s run some plays and clap our hands and snap the ball.’”

But when Gruden brought that Niners playbook with him to Philly, he tried to force it onto Cunningham instead of learning the Eagles’ system that Cunningham had been a part of since 1985. Back in April 2026, on an edition of his Gruden’s QB Class, Gruden revealed how that messed with Cunningham’s style of football.

“I got to coach Randall Cunningham, and I screwed it up,” Gruden had said. “All I wanted to do was teach him the 49ers’ offense that I learned when I was there… I didn’t know the sh*t I know now. I didn’t know all the zone reads and all the stuff we could have done. I didn’t tap into any of the stuff he had. He had it all.”

After the Eagles stint, Gruden earned his first head coaching role with the Oakland Raiders (1998 – 2001). In his next role as HC for the Tampa Bay Buccaneers, he even earned himself a Super Bowl ring (XXXVII). But for Randall Cunningham, things didn’t go as well. He had a spectacular 1998 season with the Vikings, but as his performance dipped in 1999, he reverted back to being a backup – a role he couldn’t shake off with the Dallas Cowboys (2000) and the Baltimore Ravens (2001).

Would the Eagles have been able to get more from Cunningham if Jon Gruden wasn’t their offensive coordinator in 1995? That’s a rhetorical question nobody can accurately answer now. But for Gruden, how he handled that year remains a source of regret even now when he looks back on his coaching journey.