Whether it was the coolness of Derek Jeter, the simmering intensity of Andy Pettitte, the self-flagellation of Paul O'Neill, the fiery nature of Jorge Posada, or the ice-water coursing through Mariano Rivera's veins, the players who made up the New York Yankees' last great dynasty all had something in common: an insatiable desire to win.
Over the last several years, the club has lost the plot. The last World Series victory came back in 2009. We're pushing nearly two decades without a parade through the Canyon of Heroes.
And while a lot has changed, including who calls the shots in the owner's box, a lot of what goes into creating a winning formula hasn't.
These days, the Los Angeles Dodgers have captured that magic. Their bloated payroll and disregard for luxury tax lines certainly have a lot to do with it, while Hal Steinbrenner has consistently whined that a $300 million payroll shouldn't be necessary to win, but it's more than the amount of money that is spent.
Instead, as Dodgers president of baseball operations Andrew Friedman recently put it, it's about getting the right kinds of personalities together in your clubhouse.
Andrew Friedman's comments shine a light on one of the biggest issues plaguing the Yankees in recent years
Friedman, of course, was talking up his team, but his sentiments ring true. "I can't say enough about our guys, the culture that has been created within them, and just how much they care about winning," Friedman explained. That is what he believes truly sets the Dodgers apart.
Dodgers President of Baseball Ops. Andrew Friedman emphasizes the importance of bringing in the “right” kind of players into a clubhouse:
— MLB Network (@MLBNetwork) December 10, 2025
“The type of person, the work ethic, how much they care is really important to us…”
MLB Network + @SageUSAmerica pic.twitter.com/TjrDWZ04Tg
That's a stark contrast from watching Anthony Volpe whiff, whiff, and whiff some more in the ALDS against the Toronto Blue Jays when he struck out 11 times in 15 trips to the plate, each time returning to the dugout with an emotionless blank stare.
When you see Devin Williams fail to update his social media bio to reflect pitching for the Yankees for the entirety of 2025, and then troll fans with a childish message about how they were all mad that he signed with the Mets, it becomes clear that he's not a player who values winning above all else.
And the Yankees have acquired far too many players without the necessary drive and determination for success.
It's bigger than just being able to handle New York. Heck, Paul O'Neill will tell you constantly how he's just a country boy from Ohio. Mariano Rivera came from a tiny fishing village in Panama and grew up playing baseball with a milk carton for a glove. Andy Pettitte's Texas drawl gives away where he comes from the moment he opens his mouth to speak.
It would have been easy for any of them, and many others who made up the last great Yankees dynasty, to be overwhelmed by the city, the media, the fans, and the expectations. But they weren't because, in their minds, winning was the only thing that mattered.
Until the Yankees get back to making that drive to win the primary characteristic they look for when acquiring players, they'll continue to fall short and end their seasons prematurely with a shoulder shrug. It's frustrating to see a franchise that had the blueprint for success stray so far from its roots, but that's the point we've gotten to now, and it needs to stop.
