It was back in 1986 that Jon Gruden started his coaching journey, and since then, he has spent years mentoring the next generation of quarterbacks. And while he has etched several success stories during his career, a recent session saw him candidly admit he feels he failed a legendary QB, Randall Cunningham.

During Gruden’s QB Class episode with Arkansas quarterback Taylen Green, released on April 16, the former Eagles coach explained that the workout is meant to feel like a professional meeting. It focuses on sharpening a young quarterback’s mechanics, football IQ, and mental toughness as they prepare for the NFL Draft.

In the middle of a conversation, Gruden paused and reflected on his early coaching days in Philadelphia. He used that moment as an opportunity to advise Green on how best to leverage his skills, something he believes he failed to do for the legendary Eagles quarterback.

“I got to coach Randall Cunningham, and I screwed it up,” Gruden said. “All I wanted to do was teach him the 49ers’ offense that I learned when I was there… I didn’t know the s— 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.”

Before becoming a successful head coach, Gruden spent time with several teams in coordinator roles. In 1995, his path crossed with Cunningham when he served as offensive coordinator for the Eagles.

It could have been a special pairing, but Gruden now admits his approach held things back. He tried to fit Cunningham into a system he had learned under George Seifert and Mike Holmgren after their Super Bowl success, instead of building around Cunningham’s unique skill set.

Cunningham played just seven games that season under Gruden’s watch, starting four, before stepping away from football. He later returned with the Minnesota Vikings in 1997. Both men eventually found success in their own ways. Cunningham had a standout season in 1998 with Minnesota, while Gruden went on to win a Super Bowl in 2002.

After more than four decades in the NFL, Gruden joined Barstool Sports in November 2024. He now appears on shows like The Pro Football Football Show, Wake Up Barstool, and Gruden’s QB Class.

On the other hand, Cunningham continued playing until he retired in 2002. However, even years later, the legendary quarterback has still not been inducted into the Hall of Fame.

Randall Cunningham is still waiting for a Hall of Fame call

Randall Cunningham was the Eagles’ second-round pick and the first quarterback selected in the 1985 NFL Draft. He went on to become one of the most exciting players of his era, spending most of his career with the Philadelphia Eagles and also playing for the Minnesota Vikings, Dallas Cowboys, and Baltimore Ravens.

Over 16 years, he played in 161 games with 135 starts. He ended up with 29,979 passing yards and 207 touchdowns. He received four Pro Bowl selections.

Despite all that, Cunningham has never been selected for Pro Football Hall of Fame induction. In September 2025, he became one of 128 Modern Era nominees but failed to move forward due to stiff competition. His playoff performance is usually mentioned as one of the reasons, as it includes a 74.3 passer rating, 12 touchdowns, and 9 interceptions in 12 postseason games.

However, his impact on the Eagles cannot be denied. During his 11-year career with the Eagles, he played 122 games and registered a record of 63 wins, 43 losses, and one tie. His passing yards were 22,877 with 150 touchdowns at a 55.7% completion percentage.

On August 15, 2002, he signed a one-day contract to retire in the Eagles’ uniform. Nicknamed “Ultimate Weapon” of the Eagles, Cunningham became part of the Philadelphia Eagles Hall of Fame in 2009 and the College Football Hall of Fame in 2016.

While Canton continues to wait, Cunningham’s legacy as a game changer remains firmly intact.