Derek Jeter may never let Colin Cowherd off the hook.
After Jeter’s first appearance on The Herd around the All-Star Game in 2024, the veteran radio host went viral after misremembering the timeline of Jeter’s legendary career. During the interview, Cowherd asked Jeter what it was like to face Hall of Famer Nolan Ryan on the mound, only for Jeter to hilariously correct him in real time that their careers did not overlap.
“I never faced Nolan, slow down,” Jeter laughed. “No, I was way after Nolan.”
In fairness to Cowherd, Jeter’s rookie season came just two years after Ryan’s retirement.
But Jeter got another opportunity to rib Cowherd about the mistake on Monday, as the former New York Yankees star once again joined The Herd to promote Fox’s coverage of the All-Star game. And he did not pass it up.
“Before we get started, I just want to remind you … you just said, ‘Smart people make mistakes,'” Jeter said. “Last time I was on your show, you asked me about facing Nolan Ryan, so let’s just hope you got your facts straight this time.”
“Last time I was on your show, you asked me about facing Nolan Ryan. Let’s just hope you got your facts straight this time.” – Derek Jeter sets some ground rules before his appearance with Colin Cowherd https://t.co/CqKJgftqZe pic.twitter.com/ERwA1TdqHH
— Awful Announcing (@awfulannouncing) July 13, 2026
Jeter clearly has Cowherd’s respect and handled the gaffe cleverly, especially for someone MLB fans typically think of as defensive and dry on-air.
Jeter will be part of Fox’s studio coverage for the All-Star game on Tuesday night at 8 p.m. ET.
About Brendon Kleen
Brendon is a Media Commentary staff writer at Awful Announcing. He has also covered basketball and sports business at Front Office Sports, SB Nation, Uproxx and more.