At some point between the dismissal of Joe Torre and the cementing of Brian Cashman's status as emperor, the New York Yankees lost the impenetrable aura that made them undeniably the most important franchise of the 20th century.
Greatness can't last forever -- or, at least, it shouldn't, given the sheer amount of ebbs and flows in the MLB rule book, from regional scouting to free agency to the luxury tax to the information age. And, yes, the modern Yankees, post-2009, have still been mostly very good. As Aaron Boone said last week, they've "probably" been "one of the best clubs in the league" in "certain years".
But the Yankees haven't been the iconic destination stars flock to in order to win a championship for quite some time now. Say what you will about Juan Soto's aging curve, but he turned down a $760 million offer to stay in pinstripes, and chose the Mets' trajectory instead. That would never have happened in one trillion years in the mid-2000s, or the mid-90s, or the mid-70s, or the mid-50s.
Aaron Judge certainly remains championship-focused. His mindset would've fit perfectly in this clubhouse in any era. But what about those in charge, who believe that the Yankees have built a title-winning team, but just haven't gotten the bounces yet to properly crown themselves? There's a middle ground between "World Series or Bust!" and "We'll Win It, We Just Have to Get the Breaks..." and the modern Cashman Yankees simply cannot find it -- or maybe they don't believe it exists.
It does not seem accidental that the Yankees receding from being the envy of every other franchise to being the butt of every other franchise's celebration coincides with Cashman (and Boone) somehow becoming invincible, while franchise icons find themselves spread across the game, sowing seeds of wisdom with the rest of the league.
We may never know the full story of his exit, but Reggie Jackson, feeling as if the Yankees' past championship glory wasn't being respected and that his input wasn't being valued, left for a position in the Houston Astros' front office. Houston has produced more bonafide playoff winners than any other franchise since the Yankees' last reign, from Jose Altuve to George Springer to Carlos Correa. Jackson claimed he left the Yankees because he felt like a "hood ornament" in New York. It should've been a lesson to Cashman and Co. that honoring your past should go further than Old-Timers' Day, especially when your past is more expansive and greater than anyone else's.
And then there's Don Mattingly, who Yankees fans can't help but feel for as he heads to his first World Series in his entire career, but also can't help but be somewhat agitated he's doing so as a member of the Toronto Blue Jays family.
The Blue Jays thought so much of Mattingly's intangible leadership qualities that, despite elevating him to a hitting advisory role in 2024, then watching the offense crash and burn, they still retained him and brought him back as the bench coach in 2025. The Yankees didn't hold him in similar regard; they gave him an interview to fill Torre's shoes in 2007 and most presumed he'd be the favorite for the job. Instead, they gave it to Girardi, and let Mattingly exit in less than graceful fashion. He quickly joined Torre in Los Angeles, rising to the role of hitting coach by midsummer.
Mattingly, who played in an era without a Wild Card until the tail end of his career, then saw his lone playoff run crash and burn at the hands of the very same Mariners he helped defeat last night, retired as an active player just as the next wave of Yankees greatness was beginning. With an extra playoff spot, he might've had a few more bites at the apple. Instead, he played during the previous "low point" in modern franchise history.
Despite not being on the field, Mattingly was reportedly crucial to the early development of Derek Jeter, who extolled his virtues on the Fox postgame show in the wake of Toronto's celebration. Mattingly's career full of near-misses came during the height of Steinbrenner's untenable rage, sure, but it also came with Billy Martin and Yogi Berra in the dugout, firmly holding onto the era-transcending cable running through time as the owner attempted to steer the Yankees off course.
These days, the only connection to the past the Yankees still lean on is Cashman's late-'90s dynastic coattail ride and Boone's singular home run, which came in a postseason where the Yanks lost the World Series to the Marlins.
Somewhere along the way, Yankee fans had to grow into the types of people who were happy to watch Mattingly reach his dream in the dugout of one of their rivals, knowing full well the door to their clubhouse had closed.
The Yankees' coaching staff doesn't have to be filled with the greats of yore for them to make an impact on the team's timeline. They just have to feel included. For whatever reason, the ghosts seem to have mostly gone to sleep as Cashman's power has increased, and you can trace the pattern directly to Mattingly and Jackson symbolically popping champagne in Toronto and Houston.