Remember the line from “The Great Gatsby” in which the protagonist fights the notion of being unable to repeat the past? Although it is a slippery slope, the Yankees, more than any other team in baseball, must—in the first step towards a journey to the top spot in the sport—look to their past. It isn’t about trying to recreate exactly what we once saw because that can never be done; it’s a necessary effort to understand the disconnect between the fan base and management as to what exactly dictates
desired success and how far off they are from each other.
Before the late ’90s dynasty, the Yankees had lean years as a trigger-happy team in the hands of George Steinbrenner. Winning it all was all that mattered, and the inability to see certain moves through created plenty of turmoil. That is not what we want, but nearly as disappointing is the current feeling that the front office is content with a ticket to the dance and let it be what it will once it arrives.
The Yankees are now coming up on nearly two decades without a World Series title. And with a winning club for the entirety of this run plus resources second to none in the American League, it is unfathomable that not only have they not won a title, but they also haven’t come close to one—going down 3-0 before losing the World Series in five in misery back in 2024, their sole appearance to the Fall Classic since 2009.
Plenty of the Yankee teams in this period have been good, even very good, but have any of them been great enough long enough that you could justify management’s conformism with just running it back enough times until they eventually pull through? There are tough breaks here and there, but if we look through the list of the most dominant teams in the sport over the past 10 years or so, how many Yankee teams could make the list? How many times did it truly feel like an injustice that they came up short? It has routinely seemed like the 2018 Red Sox, the 2020 Dodgers, and the 2022 Astros have been more well-rounded, naming a few.
So much of the focus is on Aaron Boone for continuously dropping playoff series against teams with a better record. Obviously he has a lot of blame there, but can we stop to figure out why the Yankees keep coming up against superior opposition in the postseason in the first place? Take these last two seasons, for instance: the Yankees couldn’t even be the best team in their division. And it’s not as if, outside of Aaron Judge’s missed time, you could point to a high level of underperformance in the regular season that’s a factor among other sustained contenders. In fact, several of the key players performed well above expectations, such as the likes of Ben Rice and Cam Schlittler.
Disappointment comes in different shapes and sizes. The one from the last two seasons is much more about the built-up frustration of a long drought than the letdown of a team you truly believed would win it all. The here we go again feeling has gotten a little too familiar.
That said, the Yankees don’t have a talent issue, but you can count on one hand the number of times during this run that they fell short of a title, and you truly felt like they got the short end of the stick as the top team. That should be the goal—not to build just one of the very good teams, but to be the absolute best, and then if you are, eventually the breaks are going to go your way—eventually you’ll make your own breaks.
