Inside The Pinstripes

Pressure Mounting for Yankees Championship

The New York Yankees haven't won the World Series since 2009.
Feb 12, 2026; Tampa, FL, USA;  New York Yankees right fielder Aaron Judge (99) during live batting practice during spring training workouts at George M. Steinbrenner Field. Mandatory Credit: Kim Klement Neitzel-Imagn Images
Feb 12, 2026; Tampa, FL, USA; New York Yankees right fielder Aaron Judge (99) during live batting practice during spring training workouts at George M. Steinbrenner Field. Mandatory Credit: Kim Klement Neitzel-Imagn Images | Kim Klement Neitzel-Imagn Images

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The New York Yankees are the winningest team in baseball, with a whopping 27 World Series titles, but that doesn't mean there's no drive to keep winning. In fact, the Yankees might just have more pressure than any other team to secure their next World Series title.

The Athletic's Jayson Stark polled 36 executives, scouts, coaches and managers and asked which teams will be feeling the pressure to win the most this season. Unsurprisingly, just under a third of those polled named the Yankees.

"I'm saying the Yankees, just because they're on this list every year," one rival exec said. "They're pretty much always the answer to this question, and they bring it on themselves. Those 27 (championship) flags will bring it out on you every time. It's been so long since they won, that pretty soon, those Red Sox fans are going to start chanting, '2009,' the way the Yankees fans used to chant, '1918,' at them."

New York Yankees outfielder Aaron Judge
Oct 30, 2024; Bronx, New York, USA; New York Yankees outfielder Aaron Judge (99) drops a fly ball during the fifth inning against the Los Angeles Dodgers during game five of the 2024 MLB World Series at Yankee Stadium. Mandatory Credit: James Lang-Imagn Images | James Lang-Imagn Images

It's no secret that the Yankees have a certain degree of expectations surrounding them because of their tremendous winning history. In the last thirty years, the Yankees have won five pennants, so a drought of 16 years, especially one that includes a World Series loss, is an excruciatingly long time to go without success. Though other franchises, like the Cleveland Guardians, who boast MLB's longest championship drought of 78 years, have gone without winning for longer, the Yankees have bigger expectations.

Yankees Players Hungry for World Series Championship

New York got insanely lucky when drafting Aaron Judge in 2013. Just four years after taking home their 27th championship, a generational player fell to the perfect spot in the draft. Now, the Yankees have to avoid wasting him.

Despite all his accolades — from AL Rookie of the Year, to three AL MVP awards — Judge is stil searching for that final accomplishment.

“I think I’d trade every award I’ve gotten and every All-Star appearance for an opportunity to win a championship,” Judge said last November.

With Spring Training games finally under way, the pressure is on. Aaron Boone's seat gets hotter and hotter as time goes on, and it's not just Judge who feels the urge to win it all. Jazz Chisholm Jr. has his sights set on not just a World Series ring, but an MVP award as well. Cody Bellinger said in a radio interview earlier this month that a championship parade in New York is his ultimate dream.

The Yankees are hungry for a win: they just have to take it.

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Delilah Bourque
DELILAH BOURQUE

Delilah Bourque is a writer and copyeditor based out of Pittsburgh, PA. She received her Bachelor's degree from the University of Pittsburgh in 2021. After a few years in corporate marketing, she joined On SI as a full-time copyeditor and contributor to the New York Yankees On SI, as well as occasional contributions across the Pittsburgh Pirates and Pittsburgh Steelers on SI.