Dec 21, 2022; Bronx, New York, USA; Aaron Judge poses with Derek Jeter during a press conference after being named captain at Yankee Stadium. Mandatory Credit: Jessica Alcheh-Imagn Images Jessica Alcheh-Imagn Images

Yankees Looking to Extend 33-Year Streak

Originally posted on New York Yankees on SI
By Joseph Randazzo | Last updated Sep 9, 2025 3:30 PM ET

With a win over the Detroit Tigers at home, the New York Yankees will extend a streak that began in 1993. That's 33 consecutive seasons with a winning record.

Since 1993, the Yankees have 3,003 wins. The organization has won five championships, eight pennants, and were first in the AL East 16 times. The Yankees lead baseball with 6,766 home runs, are third in hits with 47,024, and third in batting average with. .266. They are also tied for first with the Boston Red Sox with a .782 OPS.

H. Darr Beiser-Imagn Images

During this span, the team home run leader is Aaron Judge with 358. Second to him is Alex Rodriguez, who has 351 homers. The team leader in Fangraphs War is Derek Jeter with 73. Second to him is Judge, who has 59.3. Jeter also amassed 3,465 hits. Bernie Williams is a far second with 2,187.

On the pitching end of things, Andy Pettitte has the most wins in the organization with 219 during this span. His 57.1 WAR, according to Fangraphs, is first. Second to him is Mariano Rivera with 39.1

The closest the streak came to snapping was in 2023, a year before the Yankees returned to the World Series. Andy Martino wrote for SNY that season that league executives are in "awe" of Brian Cashman's ability to extend the Yankees' ability to compile winning seasons. It's the opposite of fan reaction. If the typical social media user were asked about Cashman, they would already have his walking papers written up. Most felt this way, dating back to losing out on Cliff Lee, or even that atrocious collapse in 2004.

During that lackluster 2023 season, Aaron Boone was asked about the streak. It was an interesting time to do so, given that the Yankees were on the way to missing the postseason. His answer was a dismissive one.

"I acknowledge the streak as impressive, especially when you frame it (as the second longest in baseball history) and all that," Boone said that season. "It is remarkable, but we go into certainly every season since I've been here with loftier goals than that."

The Yankees don't appear to be in danger of missing the postseason this year, but if they have an early playoff exit, milestones such as the years of consecutive winning seasons won't matter. All that matters to fans is a 28th championship. Anything less than that is a disappointment.

Unrelated to sports, the world since the Yankees last had a losing season is a different one. Smartphones are essentially alien technology compared to the rotary phones in everyone's homes at the time. As far as history goes, the events from 1992, the last time the organization had a losing season, are now taught in school. You had the Rodney King riots, the end of apartheid in South Africa, the debut of Barney the dinosaur, Hurricane Andrew, Bill Clinton beating George Bush in the presidential election, and the Dream Team winning the gold in Barcelona.

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