New York Yankees Might Have a Culture Problem

The New York Yankees have turned into a bit of a laughing stock when it comes to the MLB playoffs, which is not something we thought we would ever see.

For the second straight year, the Yankees find themselves in a 2-0 hole against an AL East squad. Last October, it was the Toronto Blue Jays. This time, it's the Tampa Bay Rays.

Yes, two divisional opponents that were once doormats for New York.

The Yankees have a $308 million payroll, and yet, they are on the brink of losing to a club that ranks 28th in baseball in that category. What is going on?

We sit here and make fun of the Mets all the time, and, well, we should. They're the Mets, after all. But the Yankees are supposed to be different.

The Yankees aren't supposed to be constantly losing in the postseason. They are supposed to be showing everyone why they have 27 championships, the most of any team in any major professional sport.

Instead, all the Yankees have been doing is showing their playoff incompetence.

New York has not won a World Series since 2009, which marks the club's only championship since 2001. And since last winning a Fall Classic, the Yanks have only participated in one World Series since, which came in 2024 when they fell to the Los Angeles Dodgers (the new Yankees) in five games.

But what exactly is the issue?

Yes, I understand that Aaron Judge is sidelined and that Giancarlo Stanton has had one at-bat since April 24. But both players were healthy last year when New York was embarrassed by the Blue Jays.

On paper, the Yankees should be stampeding over these teams. They have the talent. They have the big names. They don't really have any glaring weaknesses. So why is it that they keep losing to opponents that should otherwise be inferior?

Could it be that New York simply has a culture problem?

Plain and simply, the Yanks have forgotten how to win when it matters. They used to be experts at it. They could be down in a playoff series and you still knew they would somehow find a way to win. That is no longer the case.

What other explanation is there?

New York has arguably the best starting rotation in baseball. Its lineup, even without Judge and Stanton, is impressive. The Yankees also ranked second in the majors in bullpen ERA this season.

Could it be Aaron Boone, who actually did a fine job navigating around a mountain of injuries during the regular season? Is it something upstairs with Hal Steinbrenner and Brian Cashman? Is there an organizational stench that is permeating the locker room in October?

The Yankees are locks to make the playoffs virtually every year. We know that. They have missed the postseason just five times since 1994. You can pretty much pencil them in.

But what New York does when it actually gets there is another story.

It's hard to pin down an identifiable problem with the roster. Maybe, just maybe, the Yankees are now suffering from the same curse as their little brother in Queens. Just not as extreme. God forbid.