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Derek Jeter has never been one for drama, but his decision to skip the Yankees’ upcoming Old-Timers’ Day has stirred up a storm anyway, per NYPost. As the Bronx Bombers prepare to celebrate the 25th anniversary of their 2000 World Series team on August 9, one of its most iconic leaders will be watching from home. Jeter's reason? Family first.
Jeter reportedly opted out to celebrate his daughter Bella Raine’s eighth birthday, a move that might resonate with most parents. But some New York sports voices are having none of it. WFAN’s Boomer Esiason called Jeter’s decision “elitist,” arguing the former captain should be present for such a milestone celebration.
Derek Jeter is ‘elitist’ for skipping Yankees Old-Timers’ Day: Boomer Esiason https://t.co/McpS8jp2xe pic.twitter.com/16mOU7ZmyR
— New York Post Sports (@nypostsports) July 22, 2025
“It’s a little bit insulting … he should be a part of it,” Esiason said Tuesday morning. His co-host Gregg Giannotti echoed the sentiment, suggesting Jeter just doesn’t want fans to see him swing a bat at 51.
That same hesitance led to a much-maligned change last year, when the Yankees scrapped the traditional Old-Timers’ Game in favor of a Q&A session out of respect for Jeter’s preferences. Fans hated it. Concession stands saw more action than the field. The event that once celebrated Yankees nostalgia had become a snoozefest.
But in a strange twist, Jeter’s 2025 absence seems to have saved the event. With him officially sitting this one out, the team has revived the beloved two- to three-inning baseball game featuring over 30 retired Yankees players. The very spectacle Jeter helped erase is now back in full swing.
Legacy vs. loyalty
While no one denies Derek Jeter’s legendary status, skipping the event—especially during a tribute to one of his championship squads—has drawn a line in the pinstriped sand. Esiason pointed out that legends like Mickey Mantle and Joe DiMaggio suited up for Old-Timers’ Day in their post-prime years. If they could pull on the uniform again, why can’t Jeter?
The irony is stark. The man who stood for Yankees tradition now finds himself on the outside of one. Whether fans see his decision as selfish or simply personal, it’s clear his absence has reshaped Old-Timers’ Day once again—only this time, for the better.
