Yankees are now risking the end of a streak that leaves rivals in awe

Aug 9, 2023; Chicago, Illinois, USA; New York Yankees right fielder Aaron Judge (99) runs to first base after hitting a single against the Chicago White Sox during the eight inning at Guaranteed Rate Field. / Kamil Krzaczynski-USA TODAY Sports

When rival executives, often mired as they are in rebuilding, retooling, reimaging and rebranding, consider Brian Cashman’s Yankees, they express awe about one fact above all others: The team has not endured a losing season since 1992.

That 30-year streak is by far the longest active in Major League Baseball (the St. Louis Cardinals are second with 15, and that will end this year). It is almost comically longer than any active streak in the American League — Tampa Bay is in second place with five.

It is the second-longest stretch of winning seasons in the history of baseball, trailing only the 1926-64 Yankees (36 seasons).

And we’re writing about it today because it’s time to say it: There is a very real chance that the streak will end this year. What began with Mike Stanley, Dion James and Melido Perez might close with Ben Rortvedt, Billy McKinney and the ghost of Luis Severino.

Lost as we often become in the moment, it’s worth zooming out to both acknowledge the Yankees’ astounding, multi-decade achievement — and the significance of its possible conclusion. Sporting a 59-56 record after Wednesday night’s lopsided loss to the lowly Chicago White Sox, the Yankees have now earned this discussion.

Over the past week, I’ve asked Cashman and other high-ranking team officials if they are cognizant of the streak, and if it is important to them. They all quickly brush off the topic, preferring to focus on trying to salvage this season’s team.

Clearly, an organization doesn’t win every year for three decades without knowing how to stay in the moment. But since they won’t say it, I will: It would be a big deal to end an era-defining streak that can’t be duplicated until 2054 at the earliest.

And if the Yankees fall out of the playoff picture, as it appears they will, the possible end of this streak will be the most significant storyline down the stretch.

This is also the reason why there will be no legitimate discussion about Cashman’s job status after this season. What employer in their right mind would consider firing an employee after 25 consecutive winning years and one disappointing one (Cashman became GM in 1998 but was as assistant GM when the streak began)? This is not going to become a thing, period.

We’re not here to dismiss fan dissatisfaction with the season. It has become almost ghastly to watch. And clearly, Cashman and his staff need to reimagine the entire roster before next year, which will require another display of flexibility like the one the GM displayed when embracing the burgeoning analytics movement two decades ago. It won’t be easy.

But we will note the extreme gap between fan perception of Cashman’s streak and the perception of colleagues and competitors.

Nearly every other general manager or president of baseball operations takes it as a given that he or she will spend several years at a time losing, or even tanking, as a path to success. Nearly all of them go through it without a fraction of the fan and media scrutiny present in baseball-crazy markets like New York and Boston.

I can’t tell you how many times I’ve heard other GMs refer to Cashman as a certain Hall of Famer, which he is, and as one of the very best to have done the job. They say this because he finds a way to win across eras, and without ever taking a three-to-five year break. Virtually no one else knows how to do this.

Rivals don’t often cite the Yankees’ high payrolls as a reason for this streak, because no other rich team has won this frequently. They see only accomplishment.

But that particular accomplishment could end in less than two months. It is now a story to follow — and not a happy one — as the Yankees trudge toward the end of a season gone sideways.

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