For as bad as you think things may be within the Yankees internally in terms of complacency and a lack of accountability, they’re worse. These Yankees aren’t just comfortable losing, they’re content with it and accepting of it. Hal Steinbrenner made that clear last Wednesday when he couldn’t answer Bob Klapisch’s question asking, “Aren’t you sick of having to explain every year why you didn’t win a championship?”
There’s nothing these Yankees are better at than holding their annual end-of-the-season press conference while the postseason is still taking place. Only once in the last 17 seasons did the Yankees not go through this traditional charade before the World Series. Well, except for 2023, when they decided to avoid the media completely after the franchise’s worst season in three decades and just skipped the end-of-the-season press conference altogether. If you watched Wednesday’s latest humiliating performance from the Yankees, you didn’t miss much. If you watched any of the previous iterations of these press conferences during the Aaron Boone era, you could have finished the sentences of Steinbrenner, Brian Cashman and Boone.
For 90 minutes, the media asked questions of Steinbrenner and Cashman about why Cashman’s latest roster failed to win yet again. Despite the purpose of the press conference being to dissect Cashman’s latest letdown, he somehow came out of the media session not looking so bad because Steinbrenner couldn’t help himself with nonsensical answers and contradictory statements. If you ever wonder why this Steinbrenner avoids speaking for extended periods (this was his first time speaking publicly since before the 2025 season), Wednesday served as a reminder. His line for this media encounter would look something like this: 0.1 IP, 5 H, 5 R, 5 ER, 3 BB, 0 K, 2 HR. Boone would tell you someone with that line had “good stuff” and “just threw a couple they would want back.”
Steinbrenner was asked about the upcoming expected lockout, for which he is leading the charge and was annoyed he was asked about it. He claimed that with the World Series beginning in two days, it was a time to celebrate the game of baseball, not talk about labor issues. It’s OK to celebrate baseball on October 22, but on December 1, it won’t be. He called the question “inappropriate.”
What Steinbrenner fails to recognize as one of the leaders of ownership vying for a salary cap is that the Yankees need the current baseball financial landscape to continue. The Yankees generate more revenue than any other team and have the highest payroll in the American League and still can’t reach the World Series. Does Steinbrenner think they will be more successful if the financial playing field is leveled? The countless monetary mistakes Cashman has made like taking on the salaries of Josh Donaldson and Ryan McMahon won’t be possible under Steinbrenner’s proposed system. The Yankees paid DJ LeMahieu more than any Tampa Bay Ray this year to not play baseball. Flushing $15 million down the toilet won’t work in a hard cap world.
The Yankees continue to live off their past. Their last championship was 17 years ago. The ’90s ended 27 years ago. I’m sure they have a pregame ceremony for the 30th anniversary of the 1998 team planned for the 2028 season and the same for 1999 in 2029 and 2000 in 2030, but then what? There are high school students who will graduate this year who haven’t been alive for a Yankees championship. The aura surrounding the franchise no longer exists. The power of the brand and what the interlocking NY represents has faded. In a salary-cap system, that will be erased completely and the Yankees will become just another franchise, if they haven’t already.
“Winning a championship is very difficult” is the phrase Steinbrenner leaned on Wednesday. He made sure to stay away from the buzzwords of “crapshoot” and “randomness” and “chance” that the Yankees’ media relations department likely drove into his head to avoid using. If any of those three words came out of the mouths of Yankees leadership on Wednesday, it would have been a worse look than Trent Grisham batting leadoff with the season on the line.
Steinbrenner mentioned discussing roster decisions with Aaron Judge several times. Steinbrenner may as well discuss such decisions with the marina dock attendant who fuels his yacht. Judge’s previous roster choices included trading for Alex Verdugo, re-signing Anthony Rizzo and preventing LeMahieu from being designated for assignment. It was just last winter that Judge openly said the three Yankees he expected to have big years were McMahon, Jazz Chisholm and Austin Wells, and they all went on to have the worst seasons of their careers. Judge is a horrific trash talker (think the 2018 ALDS Game 2 boombox incident or taunting Drew Rasmussen in July this year) and a horrible postseason performer, but the thing he’s worst at is playing general manager.
The actual general manager is pretty bad at it too. Cashman said he likes to use the phrase “evolve or die” when evaluating his team each season, which is an odd slogan to live by when you run it back with the same failed roster each season.
Cashman is sensitive to any and all criticism. It’s why he felt the need to reach out to Derek Jeter in the past for comments he made about the team on FOX, and Cashman made sure to let everyone know he reached out to others over the last few weeks who have called out the team. That must have taken several days given the list of prominent former Yankees who have voiced their displeasure with the state of the team, a list that includes Jeter, Alex Rodriguez, CC Sabathia, Anthony Rizzo and Joe Girardi.
Cashman did admit baserunning mistakes “happen more often than they should,” yet he doesn’t think there is a managerial, coaching or culture problem with the team. All of the team’s fundamental issues continue to be a mystery to everyone employed by the team except for Steinbrenner. Steinbrenner blamed the team’s inability to win the division and advance past the ALDS on the players.
“I don’t think you can pin the season on Aaron Boone or Brian Cashman,” Steinbrenner said.
“It’s two years now … and we need to get to the bottom of it,” Steinbrenner added.
Two years of what? Does Steinbrenner think the Yankees won the World Series in 2024 or at some point in the last 17 years? This isn’t a two-year problem. It’s at best a Boone-era problem, which is now nine years complete, and it extends to the eight years before that as well. All of which Cashman has overseen.
“Winning 93 games is not a failure. Playing in the division series is not a failure,” Steinbrenner said with the most Hal quote of all time. If there was a little part of you that thought the team still cared about winning championships, that line from Steinbrenner puts an end to that.
Boone didn’t come out looking as bad as Steinbrenner did, but he was close. Boone is only capable of answering the everyday questions about why his offense sucked and why one of his low-IQ players ran into an out on the bases. Boone typically has several innings and sometimes hours to construct responses to anticipated questions about his team’s performance. But when Boone is put in a setting like Wednesday, he looks like McMahon trying to field a routine ground ball to open a playoff game.
At last year’s version of this press conference, Joel Sherman asked Boone, “What would make people believe that a team put together by the people who are putting this team together managed by you with Judge as the centerpiece will ever actually figure out a way to get to the finish line first?” Boone responded with, “I don’t know. I don’t know what to tell you.”
This year, Sherman asked Boone why the team with him as manager only beats lesser teams or AL Central teams in the postseason. Boone’s response? “I don’t have that answer for you.”
Asked about his future as manager entering the final year of his contract, instead of providing a worthwhile answer that would make fans believe he could figure out the job in Year 10, he instead said, “It’s in God’s hands.” So if God doesn’t want Boone to be the manager in 2028, he won’t be. Boone better pray God isn’t a fan of another AL team.
Asked if the season should only be considered a success if the team wins the World Series, Boone sarcastically responded, “Sure,” with a smug grin on his face.
He said, “In 2024, when we went to the World Series, we were a little bit more one-dimensional, but we were really good at that one dimension.” Was that dimension being unable to make simple managerial decisions (Nestor Cortes over Tim Hill) and fundamental plays (the fifth inning of Game 5)?
Boone brought up reaching the 2024 World Series as a positive several times. It’s sad that he’s done so much losing that being embarrassed in five games is his crowning achievement as manager.
“There’s one happy team at the end of the year,” Boone said as someone who has never been on that happy team, as a player or manager.
Boone said he “doesn’t know how to address” the critical comments made by Rizzo, and like his bosses, he “disagrees” with the criticism from CC Sabathia and others. Everyone is an idiot outside of the walls and offices of Yankee Stadium. No former Yankees player or manager knows what they’re talking about. The only three who know anything are the owner, who won the birth lottery, the general manager of three decades, who grew up with the owner like a brother and has never won without the core his predecessors built, and the manager, who is set to embark on his 10th season having never won anything as a manager or player. The Yankees were the most recognizable sports brand in the world when Hal took over as owner. The Yankees had a championship roster in place when Cashman took over as general manager. The Yankees had come within one win of the World Series with a young core when Boone took over as manager. Each of the three men had a flawless house built from scratch for them to live in, and all three act as if they built it themselves.
The Yankees did get a World Series appearance in 2026, it just didn’t come on the field. Prior to Game 1 in Milwaukee on Friday, a video montage was shown on the big screen at American Family Field of how each team reached the World Series, and the Yankees were the star of the Rays’ portion of highlights, serving as a red carpet to the World Series for a division rival for the second straight year and third time under Boone. All that’s left to complete the division Yahtzee is the Orioles. Who knows, maybe the Yankees will get to check that box next October. What we do know is, with the combination of this owner, this general manager and this manager, there will be another press conference like this next October and every October until a change is made.
Last modified: Oct 26, 2026
