Few traditions in baseball are as deeply cherished as the Yankees ‘Old-Timers’ Day. It’s a true celebration, blending nostalgia, history, and star power. What started way back in 1947 as a fundraiser for the Babe Ruth Foundation has blossomed into a beloved annual spectacle in the Bronx. But this year’s celebration carries an unexpected twist. The event, typically a love letter to pinstriped greatness, has become the center of a brewing storm involving none other than The Captain himself, Derek Jeter.
This year’s Old-Timers Day marks a significant milestone: the 77th edition, set for August 9. Last week, the Yankees announced Old-Timers’ Day would return this August, celebrating their 2000 World Series team. For the unversed, here’s the backstory. Last week, the Yankees announced Old-Timers’ Day would return this August, celebrating their 2000 World Series team. But the biggest star of that team, Derek Jeter, the Series MVP, won’t be there. The reason given? Reportedly, it’s because of his daughter’s birthday party.
What started as light chatter around the Old-Timers’ Day announcement has quickly escalated into a full-blown feud, punctuated by former NFL legend and proud New Yorker Boomer Esiason’s skeptical claim against Jeter. Well, the Yankees’ Old-Timers’ Day may honor the past, but this year, the headlines are being written in real time.
“I believe there’s an inaccurate part of this story out there,” the former Jets quarterback claimed on the Gio & Boomer Show on WFAN on Tuesday morning. “There is something going on, I believe. But I don’t believe it’s what everybody thinks it is. But maybe I could be wrong.“
Boomer Esiason doesn’t buy Derek Jeter’s birthday excuse for missing Yankees Old-Timers’ Day pic.twitter.com/bTUoXGxPM1
— Awful Announcing (@awfulannouncing) July 29, 2025
Esiason wasn’t buying it. On air, he insisted Jeter should absolutely show up for the event, suggesting skipping it felt “elitist.” Esiason further added, “Mickey Mantle and Joe DiMaggio played in an Old-Timers’ game together…if those guys put a uniform back on, then [Jeter] certainly can.”
Esiason also mentioned that someone in Jeter’s inner circle emailed him with the real reason the Hall of Famer will miss Old-Timers’ Day. While he didn’t spill all the beans, he did say that if the information is accurate, Jeter will be skipping the event for a family commitment—and no, it’s not a kid’s birthday party. As a New York native, Esiason’s reaction makes sense; he understands how special it is to have all the Yankee legends together for Old-Timers’ Day, and missing an icon like Jeter definitely stings a little.
But if you know anything about Jeter, you know he doesn’t let any curveballs thrown his way go unanswered.
Deter Jeter already triggered by the feud
Reportedly, Jeter is well aware of the chatter surrounding his absence from Old-Timers’ Day. Former Giants player Tiki Barber traveled to Cooperstown for the Hall of Fame ceremony and reportedly asked Jeter about it. The response was classic Captain: “He should have called me, don’t speculate about me, just talk to me!” Former player Barber quoted Jeter.
But Esiason claims he had already heard the birthday excuse and just doesn’t think that’s the full story. Even after listening to Barber recount a brief chat with Jeter at Cooperstown, Boomer is sticking to his guns. Now, Jeter is already annoyed with Esiason for calling him an ‘elitist.’ And things might heat up even more once he hears that Esiason also effectively accused him of lying.
“It bothers me when people question my work ethic. That’s when you’re talking about my integrity,” Jeter once called out the Yankees’ yesteryear boss, George Steinbrenner, for criticizing his work ethic.
While Jeter didn’t exactly fire back at Steinbrenner over the captaincy in 2002, he did talk to the media after “The Boss” questioned his work ethic and suggested he wasn’t fully focused. So yeah, we could expect a similar rebuttal from Jeter this time, especially when someone again questioned his dedication to the Yankees.
While very little ever rattled Jeter during his playing career, Esiason seems to have pushed a button with his ‘elitist’ remark and all the chatter about why Jeter’s skipping this year’s Old-Timers’ Day. Let’s wait to see what comes next from the other end.
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