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Derek Jeter trolls Colin Cowherd two years after interview blunder

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Last updated: July 13, 2026 11:40 pm
amedpost
Published: July 13, 2026
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Derek Jeter brought the high heat just the way Colin Cowherd once mistakenly thought Nolan Ryan did to the Yankees legend.

As a guest on “The Herd” Monday, Jeter reminded Cowherd of when he had to correct his comment about the Hall of Fame shortstop facing the flame-throwing Ryan.

“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. Let’s just hope you got your facts straight this time.”

Derek Jeter trolls Colin Cowherd on “The Herd” during the lead-up to
the MLB All-Star Game. @awfulannouncing/X

Cowherd laughed off the joke, not taking it seriously, and the segment continued.

Jeter was referencing when he was on Cowherd’s show two years ago and the sports media personality said he played “in the Nolan Ryan era.”

“No. I was way after Nolan,” Jeter responded. “Way, way, way after.”

While Jeter and Ryan just missed each other in their MLB careers, their peaks came at very different times.

The legendary pitcher played 27 years in the big leagues, debuting in 1966, finishing his career in 1993.

His heyday came mainly in the 1970s and 1980s.

Colin Cowherd reacts to Yankee legend Derek Jeter trolling him
on his show. @awfulannouncing/X

Jeter’s first game with the Yankees came in 1995, but the legendary shortstop didn’t get to his prime until the late 1990s and 2000s.

Jeter and Cowherd laughed off that exchange as well.

The former Yankee was brought on “The Herd” this year to talk about the MLB All-Star Game and where the game is as a whole.

Alex Rodriguez, Derek Jeter and David Ortiz are seen during MLB
All-Star Week in Philadelphia, Pennsylvania. Ouzounova / SplashNews.com

He was specifically asked about the ABS system and said that he loves it.

Jeter said there were times in his career where he felt he was seeing things perfectly and he would have been really accurate with it.

He has turned into a sports media personality in his own right since retiring from baseball, now working as a studio analyst for Fox Sports.

Jeter regularly makes appearances on MLB pregame and postgame shows.

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