Yankees' Brian Cashman and Aaron Boone keep the faith in the process despite a lack of results
Yankees manager Aaron Boone during the New York Yankees press conference at Yankee Stadium in Bronx, NY, Thursday, October 16, 2025 Credit: Ed Murray
The Yankees haven’t won a World Series in 16 years, but they deserve some kind of trophy for perfecting the art of explaining things the team apparently can’t figure out how to fix.
Thursday’s 2025 wrap-up in the Bronx provided more of the same, with general manager Brian Cashman and manager Aaron Boone combining for roughly an hour of injury updates, vague winter objectives and well-worn assurances that the Yankees will try hard again in 2026.
Cashman is 1-for-25 in delivering World Series titles since the Yankees beat the Mets in 2000. Boone is 0-for-8. The fact that both took turns at the podium Thursday means they’ll be returning for another swing, financed again by what we’ll presume to be another top-three payroll, courtesy of Hal Steinbrenner.
So why should anyone believe next year is going to be better than this October’s Division Series boot by the Blue Jays? Same owner, same architect, same shot-caller in the dugout.
We’re not saying this Bronx trio can’t finally end the second-longest title drought in franchise history, but history isn’t on their side, and it’s probably time to recalibrate our expectations regarding the Yankees’ superiority complex.
The Bronx dynasty years feel like a fairy tale at this point. No longer can the Yankees turn winning a championship into a cash transaction the way they did for that lonely 2009 crown. Without a Core Four or the biggest wallet, the Yankees are left to compete for a World Series ring like everyone else — and their track record indicates they’ve been lacking in those other areas.
Cashman summed it up perfectly near the end of his 37-minute session, using the term “championship-caliber intent” to describe the Yankees’ approach year after year. There’s certainly no disputing their intent. Steinbrenner has invested enough money to earn No. 28. But what is it about a franchise that has made the playoffs 26 out of the past 31 seasons but hasn’t been able to finish the job over the last 16 years?
Boone provided the most honest answer Thursday when asked why people should believe that running it back with this leadership group — namely him and Cashman — will get the Yankees that elusive World Series title.
“I don’t know,” Boone said. “The reality is we’ve had a really good club — in certain years, probably one of the best clubs in the league. But all I know is that it’s time to dust ourselves off and try to build another club that puts us in position to take a run again.
“I can’t answer that because I haven’t got this team to the top of the mountain. Until I do, all I can tell you is I’m confident in my ability to lead this team. I’m confident in our organization to build a team that gives us a chance to win. But ultimately I can’t tell you anything to make you feel good.”
Cashman clearly has faith in Boone. There was zero doubt that the manager would be back next season — he’s signed through 2027 anyway — and Cashman doubled down on defending Boone when asked if he is the right person to continue in that role.
There was a lot of talk about the handling of personalities in a “pressure cooker” like New York, the preparation behind the scenes and the zero-sum game that comes with navigating nine innings on a nightly basis. Cashman sees Boone as the ideal blend for this unique market, and that belief hasn’t wavered.
“These managerial jobs are so hard, so I try to keep it simple,” Cashman said. “Do they have a good process? Are they spending the time to assess the opponent, the scouting reports, the numbers, the players that they have? If they do all that work, I feel like I got a good one.
“He’s had a lot of success in the regular season. He’s had some success in the postseason. I think he’s one of the better managers, and in this environment, if he was out there right now, he’d get a job rather quickly . . . I trust him. I think he’s a good man.”
But even with that synergy between the manager and front office, it was interesting to hear their diverging viewpoints on the status of their newly repaired shortstop, Anthony Volpe, who had surgery for a left labrum tear earlier this week. Boone repeatedly said he didn’t think Volpe was significantly impacted by the injury; Cashman thought otherwise and suggested it got worse over time (as evidenced by his plate collapse during the ALDS against Toronto).
Neither one gave a satisfactory explanation as to why Volpe continued to play every day despite his cratering post-injury performance, especially when they had another viable option in deadline pickup Jose Caballero.
Volpe’s regression wasn’t what cost the Yankees a return to the World Series, but they definitely lost the AL East tiebreaker in the margins, and any number of different moves — especially during their annual summer Boone Swoon — could have amounted to the one additional win that would have gotten them past the Blue Jays for the division title.
“Should I have been a little more bold with some ideas and thoughts that maybe help net us a game along the way?” Boone said. “I think that’s what eats at me a little bit.”
The Yankees have another long winter to wrestle with those decisions (just like the previous 15). And then they’ll get another chance to see if that “championship-caliber intent” carries them any further next October.
David Lennon is an award-winning columnist, a voter for baseball's Hall of Fame and has covered six no-hitters, including two perfect games.
