Why Yankees Failing to Win World Series Would Spell Disaster for Franchise

The New York Yankees are all-in for the next few seasons, but what happens if things don't go to plan and they can't win the World Series?

Mar 16, 2025; Tampa, Florida, USA; New York Yankees outfielder Aaron Judge (99) looks on against the Pittsburgh Pirates at George M. Steinbrenner Field. | Kim Klement Neitzel-Imagn Images

The New York Yankees are in a pivotal moment for their franchise, as they have focused all their resources on building for the current window of time. If things pan out, they will be able to snag a World Series title for the first time since 2009, or potentially even a few more.

If things don't work out and they fall apart, things could get extremely messy very quickly for the storied franchise.

Obviously the key piece to everything is locked down long-term with Aaron Judge on a deal through 203. However, at 32 years old, nearing 33 years old, there will be a time about halfway through that contract life where he begins to lose some of that high-end production.

Thankfully so far that has not been the case, but if things don't go the way the franchise wants here for a few more years, they may miss out on winning in his prime.

The other major concern that will come into play is Gerrit Cole, who at 34 years old is starting to show some of the signs of wear that pitchers get later into their careers.

With Tommy John surgery ahead of the 2025 season, he will miss one of the crucial years of this Yankees core. Additionally, once this season is a wrap, New York only has him under contract for three more seasons of the initial nine year deal, and who knows how those seasons look now after his surgery and with his age only going up.

Then the focus heads to upcoming free agents given the payroll is among the highest in baseball at No. 7.

Paul Goldschmidt and Devin Williams will both be in free agency after this season, Marcus Stroman has a vesting option based on his performance, and Cody Bellinger has a player option for $22.5 million before hitting free agency the next year. 2027 looks no better, with Jazz Chisholm being the headliner of that group, as well as DJ LeMahieu and Jonathan Loáisiga.

On top of all of that, Aaron Boone, despite being extended, will only be locked in through the 2027 season. Many have had mixed reviews about him which is understandable, so maybe him leaving is not the worst part of the scenario if the team hasn't won by then. Regardless, it leaves them with one more decision to make on top of all the roster questions.

With that all said, it is definitely win-now mode for the Yankees, as they head into the 2025 season down some key players, but look to make a push to the trade deadline, and hopefully the postseason when all is said and done.