
via Imago
Character Counts session during Fanatics Fest NYC on August 16, 2024 at the Davits Center in New York City Featuring: Derek Jeter Where: New York City, New York, United States When: 16 Aug 2024 Credit: MediaPunch/INSTARimages EDITORIAL USE ONLY. NOT FOR USE BY NEWSPAPERS BASED IN THE UK. Copyright: xmpi34x instar54032154

via Imago
Character Counts session during Fanatics Fest NYC on August 16, 2024 at the Davits Center in New York City Featuring: Derek Jeter Where: New York City, New York, United States When: 16 Aug 2024 Credit: MediaPunch/INSTARimages EDITORIAL USE ONLY. NOT FOR USE BY NEWSPAPERS BASED IN THE UK. Copyright: xmpi34x instar54032154
In the baseball world, inundated with several moments of glory and viral moments, it is quite rare to find someone like Derek Jeter, who lived baseball. In fact, such has been his legacy that even to date his class, consistency, and character continue to inspire young generations. Even though Jeter is no longer wearing a pinstripe, his grace and tenacity have brought him attention on multiple occasions.
Now Derek Jeter has, once again, found himself in the spotlight. But this time in a different way, since he came across something unexpected. Caleb Pressley recently asked Jeter what nickname he would give himself in a small video that he posted on X. While Jeter made a confession of going with “couple and a half”, the interviewer surely turned it into a laughingstock with his response.
“Dumba** Derek” – the nickname was given to Jeter by Caleb Pressley. As funny as it gets, the post quickly went viral for the funny name and the way Jeter reacted to it, laughing it out. And guess what, this new nickname is making its fair share of rounds among the fans as well. But it was not something new though for him.
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New nickname @derekjeter pic.twitter.com/RbvPGILJVE
— CALEB PRESSLEY (@calebpressley) June 25, 2025
In the year 2001, Jeter was named “Mr November”. For the unversed, he was the only player to hit the first home run in November during the World Series game between the Yankees and the Diamondbacks. However, the most beautiful name came up in 2003, when he became the 11th skipper for the Yankees. He earned the nickname “The Captain.” But now, after all these years, things have taken a different turn, albeit in a funny way.
Of course, Derek Jeter didn’t expect that coming face-to-face. However, he took it sportingly and burst into laughter when he heard about it. The entire conversation was intended to inject a little bit of humor into the environment. And guess what? That worked perfectly fine for everyone, as both Pressley and Jeter soon were found indulging in a laughing riot.
What’s your perspective on:
Did Caleb Pressley cross the line, or is 'Dumba** Derek' just harmless fun?
Have an interesting take?
Derek Jeter was a cornerstone of the Yankees for years. Shortly after signing with the Yankees in 1995, he helped the team to win the World Series title in 1996. He was part of the Yankees victories from 1998 to 2000.
However, now that the entire spotlight is shifted to his new nickname, fans were quick enough to share their hilarious reactions as well. Let’s take a look at how the fans reacted.
Derek Jeter’s new nickname has caused a laughing riot among the fans
Shortly after Derek Jeter is provided with the nickname, the viral clip is all over the news. And one of the first comments came from a fan named Kevin O’Connor, who’s been well-known for covering the NBA since 2013. “Lmao, didn’t see that coming.” Well, neither did we expect something like this to happen. That too from someone who is so calm and cool to sit in front of Jeter and nicknamed the legend “Dumba** Derek”. LOL. No one—literally no one—would have that amount of courage to say that, right?
Lmao didn’t see that coming
— Kevin O'Connor (@KevinOConnorNBA) June 25, 2025
Another fan, commenting in a funny way, adviced Caleb Pressley to go a little bit easy on the Yankee legend. “Easy, Caleb, don’t come at the GOAT like that, bro.” If you’re wondering why he’s frequently referred to as the greatest of all time, there should be an explanation. Other than being part of the Yankees in the World Series Championship wins, Jeter finished his career with 1923 scored runs, 3465 hits and 4921 total bases. No wonder why the fans call him a GOAT!!
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“I love that you looked the goat in the face and called him a dumbass hahahaha.” An X user took a hilarious gibe at Pressley, who didn’t shy away from speaking out the name loudly. Caleb Pressley was a former quarterback for the Tar Heels football team. He currently hosts the Sundae Conversation series on the YouTube channel. However, he is known for his humor and often interviews players, asking questions that really matter. But asking Jeter something like that and then responding with such a nickname was something new, funny, and self-assured on his part this time.
“Didn’t @kobebryant come up with his own nickname?” For sure, something new is coming up every moment. It was Jeter and then it came down to Kobe Bryant out of nowhere. However, the comment seems to align with a similar incident that took place when Kobe Bryant also came up with a unique nickname. He called himself “The Black Mamba”, which was intended to show his professional life was quite different from his personal life. Well, we cannot wait to hear some more nicknames, though, can we?
The final comment is from a fan who wants to see Pressley and Glenny in a movie. Any guesses which movie? “A Caleb & Glenny Dumb & Dumber or Jay & Silent Bob Remake Would Feed Families.” Caleb and Glenny, both hosts for the Sundae Conversation, should probably work on a sequel to Dumb and Dumber, replacing Jim Carrey and Jeff Daniels. That’s what the fan hopes to see or even maybe another movie remake that may keep them in the news all the time. The fan didn’t intend to hurt the feelings of anyone, as it was entirely sarcastic, meant to bring some smiles to the faces of many who will be going through the comment section.
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There is no doubt that Derek Jeter is adored by his fans and will remain so for years to come, regardless of what we call him or force him to do. Any other nicknames that you probably have heard of before?
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Did Caleb Pressley cross the line, or is 'Dumba** Derek' just harmless fun?