Is The Yankees World Series Window Now Closed?

The New York Yankees made the World Series in 2024 for the first time since 2009. They play in the country's biggest market, have Major League Baseball's biggest brand, play in an iconic stadium, and have one of the best hitters in the sport's history.

They own part of their own television station dedicated entirely to Yankees content, for crying out loud. So why does it feel like their window to win a World Series might be closing?

Because it might actually be closing.

The randomness of the baseball postseason means that just making it to October is enough to have a legitimate chance at a title. But the Yankees built their roster around an aging core, with few top-level prospects nearing the big leagues, and an injury-prone slugger raking in a massive salary through the 2027 season.

Then there's Gerrit Cole, who just had Tommy John surgery and is set to miss the entirety of 2025, meaning he won't return to a big league mound until likely after turning 35.

And they have an owner who's more prone to contradictory statements than putting his money behind building the best possible team. 

TORONTO, ON - JUNE 19: Aaron Judge #99 of the New York Yankees reacts to striking out against the Toronto Blue Jays in the eighth inning during their MLB game at the Rogers Centre on June 19, 2022 in Toronto, Ontario, Canada. (Photo by Mark Blinch/Getty Images)

New York Yankees Have Major Questions, Few Answers

The Yankees lost out on Juan Soto in the offseason, as he signed a 15-year, $765 million deal with the rival Mets. Their replacements range from solid, to unspectacular, to temporary.

Max Fried, though generally one of baseball's most consistent starters, had just a 3.4 WAR season last year, per Fangraphs. For context, that was around the same value as Michael Wacha and Erick Fedde, and below Yusei Kikuchi. They're paying him $215 million over the next eight years. 

Paul Goldschmidt had the worst season of his career in 2024, putting up a league average .245/.302/.414 batting line in St. Louis. Devin Williams, while still a top two or three closer, is signed for just one season. Cody Bellinger will also reach free agency after 2025, with his MVP days far behind him. Aaron Judge just put up one of the best offensive seasons in baseball history, but turns 33 in April. 

Jasson Dominguez has high expectations, though his 67 plate appearance debut in 2024 was ugly, to say the least.

With Giancarlo Stanton likely to miss most, if not all, of the 2025 season, their projected DH is Ben Rice, who was nearly 30% worse than league average on offense in 2024 and actually cost his team -0.3 wins.

It's not a cohesive, deep roster. And their owner has signaled he has no intention of spending his way out of it. Hal Steinbrenner last month, per The Athletic, expressed concern over the team's payroll, sustainability, and correlation between spending and winning. 

"Should I really need a $300 million-plus payroll to win a championship?" Steinbrenner said. "Does having a huge payroll really increase my chances that much of winning a championship? I’m not sure there’s a strong correlation there."

Steinbrenner's remarks contrast with his other recent complaints about the World Champion Dodgers and their offseason spending. "It's difficult for most of us owners to be able to do the kind of things they're doing," Steinbrenner said in January. "We'll see if it pays off. They still have to have a season relatively injury free for it to work out for them."

READ: Billionaire Yankees Owner Cries Poor, Says He Can't Keep Up With Dodgers

So which is it? Does spending not correlate to winning a championship? Or is it just too hard for the richest team in baseball to spend money and increase their odds of winning a championship?

With this level of dysfunction, poor planning, and misplaced spending, New York has very little margin for error. Now and in the seasons to come.