NEW YORK — The man who has run the Yankees for nearly three decades just admitted something that might explain a lot. He never wanted the job in the first place.
Brian Cashman made the confession during an interview that aired Wednesday on the YES Network’s “Hot Stove” program. For Yankees fans who have watched their team go 16 years without a championship, the timing could not be worse.
The Yankees senior vice president and general manager opened up about his reluctance to take the top job back in 1998. He spoke about the pressure. He spoke about the fear. And he spoke about why he almost said no.
“I never, never wanted to be the GM of the New York Yankees, I’ll be honest,” Cashman said. “It’s a very tough environment. And the GMs under George Steinbrenner, you know, didn’t last very long. It was a year, a year and a half, maybe two tops, and it was a difficult situation, no doubt about it.”
That candor would have been refreshing a decade ago. Now it feels like a confession that arrives too late.
The Yankees championship drought stretches on
Cashman inherited a dynasty when he took over in February 1998. The Yankees won World Series titles in his first three seasons. They added a fourth in 2009. Those four rings still define his legacy.
But since that last championship parade through the Canyon of Heroes, the Yankees have become a team of regular season success and October heartbreak. They reached the World Series only once in the past 15 years. They lost to the Dodgers in five games last October.
This past October was even worse. The Yankees tied Toronto for the best record in the American League at 94-68. Then they lost the division on a head-to-head tiebreaker. The Blue Jays eliminated them in four games in the ALDS. Toronto piled up 23 runs in the first two contests alone.
“They hit the crap out of the ball,” catcher Austin Wells said after the loss. “They didn’t miss, and they took advantage of every free base we gave them.”
Manager Aaron Boone was blunt. “We got beat here. Credit to the Blue Jays. They took it to us this series.”
Cashman’s complicated Yankees legacy
The numbers tell two different stories about Cashman’s tenure with the Yankees. On one hand, he has more than 2,500 regular season wins. He reached that milestone in March 2025 when the Yankees crushed Milwaukee 20-9. His lifetime winning percentage of .589 is the highest of any GM with at least 10 seasons since 1950.
The Yankees have made the playoffs 21 times under Cashman. They have won 14 division titles. No franchise has more postseason berths since 1998.
But Yankees fans measure success differently. They care about championships. And Cashman has failed to deliver one for 16 consecutive seasons. That is the third-longest drought in franchise history.
“The ending’s the worst, right?” Boone said after the ALDS loss. “Especially when you know you have a really good group of guys that came together so well at the right time.”
Steinbrenner’s shadow still looms
Cashman worked for George Steinbrenner when The Boss ruled the Yankees with an iron fist. He watched 15 different GMs cycle through the job before he took over. Most lasted a year or two. Some barely made it through a single season.
“George Steinbrenner was a tough boss and he didn’t have much patience, and he was driven to non-stop success,” Cashman said. “And in baseball, you can’t have success every day.”
That fear of failure shaped Cashman’s early reluctance. It also kept him from becoming another casualty of Steinbrenner’s impatience. He outlasted The Boss. Now he works for Hal Steinbrenner, who has never publicly embraced the championship-or-bust mentality his father made famous.
Smart enough to take the job
Despite his initial hesitation, Cashman admits he made the right call. He joined the Yankees organization in 1986 as a 19-year-old intern. He worked his way up through scouting and became assistant GM in 1992. When the opportunity to run the show arrived, he grabbed it.
“And so it was not something I was ever aspiring to be,” Cashman said. “But I was smart enough to know, when I had an opportunity offered to me by The Boss, I was smart enough not to turn it down.”
The Yankees rewarded that decision with a four-year contract extension in December 2022. Cashman’s deal runs through 2026. Boone signed a two-year extension last February that keeps him in the dugout through 2027.
Neither man is popular among Yankees fans who believe the franchise needs fresh leadership. The calls for change grow louder after every October exit. Yet Cashman and Boone remain firmly entrenched.
Aaron Judge called last year’s World Series loss a “failure.” After the ALDS defeat to Toronto, he offered a softer assessment. “Not a good year,” he said.
The Yankees led Major League Baseball with 274 home runs in 2025. They scored 849 runs. They won the American League Team of the Year Silver Slugger award. None of it mattered when October arrived.
Cashman never wanted to be the Yankees GM. Twenty-eight years later, he still has the job. The question for Yankees fans is whether that reluctance ever truly went away.
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