This Monday, when Derek Jeter appeared on The Herd to discuss the Midsummer Classic, that wasn’t the only thing on his agenda. Back on July 16, 2024, while discussing the game and various players, Cowherd referred to Jeter as someone who belonged to an era that predated his own professional debut. Jeter had to stop him mid-conversation to correct the mistake. Fast forward to now, Cowherd might have forgotten about the mistake, but Jeter wasn’t about to let it slip from his mind.

“Before we get started… Last time I was on your show, you asked me about facing Nolan Ryan,” Derek said, as per Awful Announcing on X. “Let’s just hope you got your facts straight this time.”

And before he could even finish his sentence, Cowherd burst into laughter. 

The 52-year-old is a Yankees legend, and he is known as one of the greatest shortstops in baseball. He spent the entirety of his two-decade-long MLB career in New York. The 14x All-Star helped the Pinstripes win the World Series on five occasions. 

Nolan Ryan, on the other hand, is one of the most famous pitchers. The Hall of Famer recorded 5,714 strikeouts (All-time strikeout leader) in the majors and managed 7 no-hitters. While both of these individuals were phenomenal, they were never contemporaries on the field. 

Ryan started his career in 1966 and retired in 1993. Jeter made his MLB debut with the Yankees in 1995 and concluded his chapter after the 2014 season. Derek Jeter never faced a single pitch from Nolan Ryan. While the error was huge for a baseball fan, Jeter and Colin Cowherd shared a light moment as the host tried to be factually correct for the remainder of the show. 

Derek Jeter’s callback wasn’t Colin Cowherd’s only memorable on-air mistake 

Back in 2024, Cowherd was actually discussing Paul Skenes. He was probably trying to come up with a suitable comparison and mentioned Jeter facing Ryan. The Yankees legend had to step in and stop him in his tracks. 

“No, no, no,.. Slow down. Slow down,” Jeter said. 

Cowherd tried to recover from the mistake, asking, “Not even an inning?”

“No, I was way after Nolan, way, way, way after Nolan,” was the reply.

And on Monday, the joke landed immediately for the viewers who were already aware of the previous chat. But this wasn’t the lone blunder from Colin. 

Just a year before that, he was discussing first-round football quarterbacks “who could or couldn’t win a Super Bowl.” And one of the images was of Dwayne Haskins. 

The QB had tragically passed away on April 9, 2022, at the age of 24. While this could have been an honest mistake, it still appeared insensitive, and the show earned a good amount of backlash. It was later corrected during a rebroadcast. 

However, the incident between Derek Jeter and Colin Cowherd wasn’t as serious. Rather, the duo, including the viewers, got a good laugh out of it.