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Oct 25, 2024; Los Angeles, California, USA; New York Yankees general manager Brian Cashman before game one against the Los Angeles Dodgers the 2024 MLB World Series at Dodger Stadium. Mandatory Credit: Jayne Kamin-Oncea-Imagn Images Jayne Kamin-Oncea-Imagn Images

Insider Rips Yankees After Failed Playoff Run

Originally posted on New York Yankees on SI
By Jack Markowski | Last updated Oct 18, 2025 3:00 PM ET

The New York Yankees failed to take home the Commissioner's Trophy yet again this postseason, extending their drought without a World Series title to 16 seasons.

As the Yankees try to put their ALDS elimination at the hands of the Toronto Blue Jays further behind them, the New York Post's Joel Sherman offered some pointed criticism towards the club after another fruitless October.

Yankees' Failure to Finish the Job

Sherman noted that while the Yankees are annually good enough to make it into the postseason and often win a playoff series or two, they haven't reached their ultimate goal since 2009 despite having numerous opportunities to do so.

"The organization good enough to get close to the goal line, without ever actually crossing it," Sherman wrote.

"The franchise that insists it is championship or bust annually, but has become all too familiar with bust.

"The team that can tease with title proximity, but completes each season with Brian Cashman and Aaron Boone sitting at a table at Yankee Stadium explaining again why they are close, yet not good enough."

Troy Taormina-Imagn Images

Yankees' Playoff History Under Boone

Since the Yankees hired Boone as their manager ahead of the 2018 season upon firing Joe Girardi, the club has made the playoffs on seven occasions.

During that span, New York has advanced six times and made the American League Championship Series in three instances, though the only time it reached the World Series was in 2024, where the Los Angeles Dodgers defeated it in five games.

Putting the Yankees' World Series Drought in Perspective

Since the Yankees' World Series victory over the Philadelphia Phillies in 2009, 10 different franchises have won the Fall Classic. That number would jump to 11 this year if either the Toronto Blue Jays or Seattle Mariners topple the Dodgers, who swept the Milwaukee Brewers in the NLCS.

New York's longest World Series drought in franchise history is 20 years, which stretched from its first year of play in MLB as the Highlanders in 1903 all the way to its initial championship in 1923.

The Yankees still have four more seasons to go before matching that mark, but it's certainly creeping up on them at this point.

Vincent Carchietta-Imagn Images

Will Yankees Keep Running It Back?

The Yankees are set to make a number of minor changes to their coaching staff, as bullpen coach Mike Harkey, first base/infield coach Travis Chapman and assistant hitting coach Pat Roessler all won't return, at least not in those roles, for the 2026 campaign.

Sherman acknowledged how tough it is to truly nail down the formula for a championship-caliber club, but with Cashman and Boone set to return after countless failed attempts, it's worth contemplating whether or not New York is heading down the right path towards baseball immortality.

"In other words, it is tough to get the right people to drive the right philosophy and have it all work well enough to get to the postseason and then rise in that tiny October window," Sherman wrote. "But some team does manage it annually. And year after year, for a long time now, it has not been the Yankees.

"Maybe they just need more tries with all the same folks doing the same thing.

"Or is that red zone insanity?"

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