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The Astros’ specter lingers over this generation of Yankees

Continued struggles against the Astros define the otherwise-enjoyable Baby Bomber Era.

MLB: World Series-Philadelphia Phillies at Houston Astros Troy Taormina-USA TODAY Sports

The Yankees are in a class of their own when it comes to baseball history. That fact is well-established and firmly backed by the 27 World Series titles to this organization’s name, firmly blowing the teams in any of the four major American leagues out of the water. During the late ‘90s and early 2000s, New York enjoyed one of the greatest runs of our lifetime, and there was a certain mystique about this club — particularly in the postseason that baffled many a team.

Derek Jeter talking about ghosts, and great visiting teams floundering in unimaginable fashion ... the stuff was real, and one couldn’t refute a whole different level of pressure. It was hell to try to beat the Yankees in October.

That generation came and went, accomplishing all it could have possibly imagined and then some. But here we are, several years later with the Yankees entering unchartered waters, and not because of a long drought or anything (believe it or not, that has happened even with this team in the past), but the real stickler is how it has happened: The Yankees have been Yankeed by the Houston Astros.

Historically, the Yankees have been the bully who repeatedly beats up on a particular team in October — even if it is a good one. Until the 2004 ALCS, the Red Sox simply were unable to beat the Yankees, and even today, every time the Twins see this matchup in the postseason, that crushing feeling of “here we go again” comes up. The same can be said about the Oakland A’s, who have never taken down the Yankees in a playoff series either.

The drought since 2009 certainly bothers everyone, but the three postseason series losses to the Houston Astros have created a particularly negative environment that’s new in the history of this team, especially to our generation.

Think about this for a second: Counting the last five seasons (excluding the shortened 2020), the Yankees have averaged 97 wins per year. Ninety-seven!

And yet, the feeling of success is completely overshadowed by the all-too-many playoff losses to the Astros. It’s true that we’re talking about the Yankees, and there would be plenty of disappointment anyway if these were defeats at the hands of a a few different teams. Nonetheless it has certainly added a new level. The Yankees endured brutal October losses to the Angels and Tigers between 2002-12, but this scenario over the last handful of seasons or so has fully turned the tables on this particular squad.

When a Houston Astros vs. New York Yankees playoff series comes in sight, the Yankees fans are the ones who get the “here we go again” feeling.

Consequences of this phenomenon

There isn’t an easy fix for this problem. The most recent ALCS in particular more or less highlighted a pretty clear gap between these two teams. Three of the four games were close, but it was hands-down a decisive sweep. Houston set the standard, and it is up to Yankees GM Brian Cashman and the entire front office to build a team that fans can feel confident about going toe-to-toe and beating a juggernaut that has now won two championships and four pennants in the past six years.

It’s a challenge to provide adequate criticism, while also remaining fair and realistic, and not entirely reliant on small samples. Aaron Judge and company did compete with Houston in both 2017 and 2019, and showed at times during the regular season that it could certainly do it again.

However, it’s hard to escape three series losses in a six-year span and the massive cloud that carries with you. The fact remains, if you group those three years, the Astros had better teams as a whole.

It is not as though the Yankees have found that one team capable of overcoming everything to consistently beat them in the playoffs. New York has consistently clashed with a superior team, one that has averaged 104 wins in the three seasons it beat them.

As stated above, this ultimately comes back to the front office, and the need to build better teams. The bar has been established, and it is pretty high — higher than usual, given the constantly-refreshing cycle of terrific players churned out by the Houston organization. It’s now the Yankees’ move.

The big consequence of this is that in the journey back to World Series glory, a simple playoff series win over the Houston Astros will take a significant weight off this team’s back — much like how the Red Sox probably needed to beat the Yankees when they finally got over the hump. The Yankees probably need to do the same against the Astros. We can only hope that the day comes soon, redefining this generation of Yankees baseball.