Where did the New York Yankees go? They used to make winning look so easy that the entire industry reviled them, wrote rules around them, and chased them.
But these Aarons-era Yankees experience October like a ball of yarn experiences a cat, batted around by injuries or hot teams or other autumn inevitabilities – as if they, like the yarn, do not have the ability to decide where they go.
This generation’s triumvirate -- Aaron Boone, Aaron Judge and Brian Cashman -- has won more games than everyone but the Dodgers since the start of the 2018 season. But postmortem news conferences are the lingering images of all their shared Octobers.
“Every year’s a little bit different. There’s years where I feel like we’ve been, at times throughout the year, the best team or one of the very best teams in baseball,” Boone said Wednesday. “And you get to the finish line and you’re not that same team.”
Fairly or not – and of course it is fair, because these are the Yankees, and winning is what you promise when you sign – where they are at the finish line is all that matters. The fact that their banged-up 2026 group still managed 93 wins in a tough division without their biggest star does not qualify as consolation.
Those credentials do, however, qualify Boone and Cashman for at least one more try. Cashman’s contract expires after this season, but he announced Wednesday that he has agreed to the framework of an extension that will keep him in charge for a 30th season and potentially beyond.
As for Boone, his eighth made postseason in nine chances was enough to persuade Hal Steinbrenner that Boone deserved to keep his job – though he admitted he needed a week of deliberation.
“Every year, I’m going to look at the situation. I don’t think you can pin the season and the unacceptable end to it on Aaron. I don’t think you can pin it on [Cashman] based on the roster he put together,” Steinbrenner said. “Again, the offense – not the pitching, but the offense – had a big part in why, and I don’t mind saying it, why we didn’t get where we strive to get every year.”
So the offense, it seems, will be the problem the Yankees decide to address to avoid this fate next year. Steinbrenner, Cashman, and Boone all said Wednesday they will consider making changes to the coaching staff. Boone and Cashman both said they are always trying to emulate the successful parts of winning teams, so they are enamored with the athleticism of the Rays and Brewers.
Still, they have sort of tried that already: the acquisitions of Jazz Chisholm Jr., Jose Caballero and the promotions of young players like George Lombard Jr. and Spencer Jones have certainly made them more mobile.
“I feel like we, over the last number of years, have tried to address our athleticism, our defense, our baserunning skillset with, obviously, guys that can take the extra bag or steal a lot of bases,” Cashman said. “So I think we’ve tried to steer in that direction, and we’ll continue to try to steer in that direction.”
But when the Yankees couldn’t get runners on base against the Rays a few weeks ago, it did not matter whether those runners could have stolen a base. And when their defense fell apart in the first inning of Game 2, it did not matter that their position players should have been able to do better. Cashman also mentioned the importance of contact in October success, but he did not seem convinced enough to make a full pivot away from big sluggers, either.
“You don’t lose sight of the team that outhomers the opposing team in each playoff series is the one that moves on. So slug is important, too,” said Cashman, who acknowledged that they are both always trying to emulate the strengths of successful teams but sometimes feel their hand is forced.
“But then, what’s available in the marketplace? What’s available in the trade marketplace? What’s the availability in the free agent marketplace? What’s the flexibility in the payroll when those availabilities do come? What’s coming up through your system that you gotta lean into, you believe can maybe allow you to find the higher ground with a good [controllable] player?” Cashman said.
And indeed, the Yankees’ ability to make significant change offensively is somewhat limited given the runway they will likely give Lombard Jr. at shortstop, the need to preserve designated hitter at-bats for Ben Rice while crossing their fingers Judge is healthy enough to play right field, and the need to find a position for Luis Garcia Jr. if he isn’t.
“You’re always trying to incorporate the best of some teams,” Boone said. “But you also start with a lot of certainties that you have within your club, so a lot of times you’re just trying to improve things around the margins, and hopefully we can do that this winter.”
While the repetitiveness of these October seminars suggests they have not adapted enough by Yankee standards, Boone and Cashman have shown some ability to evolve. Boone arrived around when analytics cemented new strategic norms and evaluation methods. The Yankees did not struggle with these changes and in some cases, were early adopters.
“Evolve or die,” Cashman said Wednesday, though this version of the Yankees is uniquely capable of both.
The trouble, former Yankees like Anthony Rizzo and C.C. Sabathia have suggested in recent weeks, is a decline in clubhouse and franchise standards. Rizzo said Yankees players are too uptight and that the organization repeats too many fixable mistakes. Sabathia said a lack of input from Yankees stars with championship experience is fostering a slip in accountability, though Boone said he encourages former players to spend time around the team.
As for clubhouse standards, Boone was asked whether recent playoff failures leave him thinking he needs to be more publicly vocal about his players’ failings. He does not.
“There is probably a time and place for that, but generally speaking, to me, that’s not leadership,” Boone said. “That’s me giving red meat to people that want to be upset with somebody.
Wednesday, Steinbrenner assured reporters that whatever happens publicly, players hear from him or Cashman or Boone or Judge privately when they do not meet expectations. He sees no reason to start emulating his late father’s media strategy, either.
“I’m not convinced that with this team, in this day in age, that that’s as big a motivator as you think it is,” Steinbrenner said. “Twenty, twenty-five years ago? Different generation, just a different scenario.”
In this scenario, the Yankees will bet on patience. There will be change, but it will not be drastic.
As Steinbrenner explained, he sees the offense as the problem. As Cashman explained, they will continue to add as much talent as they can within realistic limits. As Boone said, he believes they had enough talent to win, but they will try to get better at everything. And they will hope that when another unpredictable baseball autumn is done batting them around, they will end up with a title.
It seems the Octobers when the Yankees knew how to pounce are gone.
