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.

The words of Frank Sinatra’s “New York, New York” crooned at Yankee Stadium late last Wednesday night, except they didn’t come from the Stadium speakers following a Yankees win to extend the ALDS. They instead came from a champagne-soaked visitors’ clubhouse, as the Rays played the Yankees’ victory song in celebration of eliminating their divisional rival in the minimum three games.

The ritual was nothing new. It started eight years ago after the Red Sox eliminated the Yankees at the Stadium. Sinatra’s hit became the Red Sox’ victory song following the 2018 ALDS and for the rest of that postseason, when they knocked off the Astros in the ALCS and then the Dodgers in the World Series. It became their song all because of Aaron Judge.

After the Yankees won Game 2 of the 2018 ALDS to even the series at a game apiece, Judge walked out of Fenway Park blaring the song on a boombox for all to hear. Acting like the Yankees had accomplished something simply by splitting the first two games on the road, the face of the franchise’s foolish decision served as a rallying cry for the Red Sox, who had won the AL East over the Yankees by eight games that year.

Two nights later, in the series’ next game, the Red Sox handed the Yankees their worst home postseason loss in franchise history. The following night, the Red Sox eliminated the Yankees to start a near-annual tradition of the opposition celebrating the Yankees’ elimination on their field, with the song being played in the visitors’ clubhouse and continuing to play throughout the postseason even though the Yankees were no longer part of it.

Since his foolish antics on Oct. 6, 2018 at Fenway Park, Judge has spent his career acting like he has won anything other than individual awards. He carries himself like he has captained a dynasty, talks like he was part of the Yankees’ last dynasty and acts as if he has done anything other than get eliminated from the nine postseasons the team has played in during his career.

The narrative that the Yankees have failed Judge throughout his career makes me cringe. Judge has failed himself. He’s the one with a postseason OPS 200 points lower than his regular-season OPS. He’s the one who has played in 17 rounds of the postseason and has performed well in six of them. He’s the one who continues to back the manager who has overseen nine of his 10 full seasons in the majors. He’s the one who wanted the team to trade for Alex Verdugo, re-sign Anthony Rizzo and hang on to DJ LeMahieu. He’s the one who said he wanted the team to “run it back” immediately after their elimination in the 2025 ALDS. Judge isn’t absolved from the Yankees’ failures during the Aaron Boone era just because he’s the best player on the team. For as good as Judge is from late March through September, he has played a role in the disappointments of October.

Judge didn’t play in the latest postseason disappointment, but he had a lot to say about it. Judge spoke with the media for just under 10 minutes after the Game 3 loss and tried to sound as much like Derek Jeter would after his teams lost in the ALDS as he could, just without a full hand of rings to fall back on as a defense.

“It’s always tough. Any time you’re not the last team standing and lose at home like that in three straight games, it’s definitely tough, difficult.”

Then I guess Judge’s entire career has been tough since he has never been on a team that was the last team standing, just like his manager. Judge has now been on the team for five home eliminations, so it was nothing new for him. And as for losing three straight games and being swept in the ALDS, it was the first time in 25 ALDS appearances that the Yankees were swept in the series.

“You gotta tip your cap to the Rays. They had an incredible season: go out there and win a division and put the pressure on us all year.”

This answer felt a lot like Boone saying, “The league has closed the gap on us,” after the Yankees finished third in the division, fifth in the AL and were eliminated in the one-game playoff in 2021. The Rays didn’t have to put pressure on the Yankees since they led the Yankees in the division from June 28 through Game 162. The Yankees were the ones needing to apply pressure, and whenever they did, the Rays answered with extended winning streaks.

“I don’t like [the Rays celebrating at Yankee Stadium]. I don’t like other teams celebrating in our place. But if you don’t like it, you gotta play better.”

The 2026 Rays joined the 2025 Blue Jays, 2024 Dodgers, 2022 Astros and 2018 Red Sox as teams that have celebrated ending the Yankees’ season at Yankee Stadium. The Yankees have never won a best-of-5 or best-of-7 series at home during Judge’s career, so all he knows is other team’s winning series at his home ballpark.

When asked what his message is to Yankees fans, Judge said, “That’s tough,” then paused for six seconds to try to recall past years’ excuses in his brain, and responded, “We gotta be better. None of us are satisfied.”

I would argue they are satisfied, considering nothing changes. Each season, the Yankees start out well, slump during the summer months, rebound at the end of the regular season and then go home early in the postseason. Rinse and repeat. They show up, do enough to get by and then do it all again the next year. They are content with losing and satisfied with the results.

“We’re the Yankees. I feel like [the front office] should go all in and do what they need to do. If we got holes, if it’s finding certain players or personnel or whatever we need you gotta go out there and get it. That’s why I signed back here to play with the yankees is to fight for a championship and go all in.”

The Yankees have spent roughly $2.5 billion on payroll during the Boone era for zero championships. What does Judge consider all in? A $400 million payroll? A $500 million payroll? A team with roughly a $100 million payroll is going to win the 2026 World Series, whether it’s the Brewers, Rays or Guardians. Judge, Giancarlo Stanton and Trent Grisham made just under $100 million in 2026. Those three are equal to the combined payroll of the 26-man roster of whichever team wins the World Series.

“[The front office] give us a winning team every single year, but that’s not good enough here in New York. We’re the Yankees. You gotta go out there and expect championships and go all in every year.”

Let’s stop with the “expect championships” line. Judge has never won a championship. The organization hasn’t won a championship in 17 years. The championship-or-bust mantra is dead. At this point, it’s as meaningful as the Mets or Pirates saying they expect to win a championship.

“He’s our manger,” Judge said of Boone. “He’s running this ship. He puts us in the right position to go out there and succeed … He’s definitely had our back and is a guy.”

He’s definitely a guy, as in, yes, Boone is a male. If Judge wanted the Yankees to have a different manager, the Yankees would have a different manager. So whatever losing problem or culture problem or accountability problem the Yankees have, Judge has played a large part in them having that problem. He’s the team’s best player (when he plays). He’s the team’s highest-paid player. He’s the captain. He’s the face of the franchise. And he’s the one running out of time to change a legacy that will be one of being the face of the franchise during the team’s longest championship drought, an era of disappointment and underachievement.

It has been interesting to see Judge’s personality and media presence change in recent months. He used the media to have a back-and-forth with Boone when he was rehabbing his rib injury, openly questioned being pulled early from his first game back from that rib injury and handled the mid-September calf injury as poorly as he handled the fly ball hit to him in the fifth inning of Game 5 of the World Series.

Last offseason, in an interview with Kevin Durant, Judge said three players he was excited about were Jazz Chisholm, Austin Wells and Ryan McMahon.

“He can be one of the greats in the game,” Judge said of Chisholm. “I think this will be a big year for him to take that next step.”

Chisholm had the worst season of his career.

“I think this will be a big year for him,” Judge said of Wells, “he’s really going to take that next step.”

Wells had the worst season of his career.

“I think there’s just so much more potential,” Judge said of McMahon. “I think what he’s about to do with the bat this year, he’s going to take off for us.”

McMahon had the worst season of his career.

Just like when he walked by the Red Sox’ clubhouse with his boombox, when Judge speaks, nothing good comes from it.

Is there an ex-Yankee or current media member left who hasn’t criticized the current state of the Yankees and called for change? I don’t know what took everyone so long. I have been beating that drum for most of the nine years of the Aaron Boone era, but it took everyone until now — a second straight embarrassing ALDS exit — to realize the Yankees are no longer the Yankees and haven’t been for a while. Derek Jeter, Alex Rodriguez, CC Sabathia, Anthony Rizzo, Michael Kay, Mike Francesa, Joel Sherman, Jon Heyman and Ian O’Connor have all finally come around, but it won’t matter. There’s nothing the Yankees enjoy more than telling the world what they witnessed didn’t take place, even if the world has been watching the same season and ending for most of the last decade.

We know there is a lot of delusion within the organization. The general manager called the 2023 team “really fucking good” after they went 82-80. The manager has an excuse and a positive outlook for any and all situations. The players tell you they will make poor decisions “again” because there is no one to hold them accountable. The Yankees as a roster are a group of soft losers who were molded into soft losers by their manager and their front office. The owner doesn’t care if the team wins as long as the line on the revenue chart keeps going up, the general manager doesn’t care how the manager is perceived as long as he’s doing what the front office wants him to do, and the players are more comfortable losing than winning because all they know is losing.

There’s this narrative out there that the Yankees haven’t met with the media yet for their end-of-the-season press conference because Brian Cashman doesn’t have a new deal in place. If you believe that, then you probably believe the organization cares more about winning the World Series than winning 93 regular-season games. Cashman didn’t have a contract at the end of the 2022 season, and the team still held their annual “We came up short” media session despite it. So the idea that they are waiting until Cashman gets a new deal is a stall tactic.

It could be a stall tactic that leads to them not meeting with the media at all. If you remember, they did this after 2023 when the team posted the franchise’s worst regular-season record in three decades. Things were bad then, but not nearly as bad as they are now. Each day former players (who played under Boone or were teammates with him), prominent media members and even current Yankees and YES employees are taking shots at the team. If the Yankees were to trot Cashman and Boone out there right now, it would be a disaster. Maybe not for Cashman because he has a way of just talking and talking endlessly in nonsensical speak, but certainly for Boone, who lacks improv skills. It was just last year that Boone was asked, “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?” and he responded with, “I don’t know. I don’t know what to tell you.”

I could see the Yankees holding their press conference on Tuesday, Oct. 20. That’s the same day the Knicks open their season at Madison Square Garden by raising their championship banner. What better way to address the stink that lingers on this awful Yankees season than by having the celebration of the Knicks mask it? There’s something poetic about a team that recognized its head coach couldn’t get them to the promised land, so they changed head coaches and won the championship the very next season celebrating said championship possibly on the same day the Yankees give the keys to their championship-less manager for a 10th season.

There’s really no need for the Yankees to hold their end-of-the-season press conference anyway. We all know Cashman is getting a new deal and Boone is returning. The duo will say that Boone is under contact for 2027, so why would they need to address his job status? There is nothing that is going to come from the press conference other than an injury update that could just come from a team press release or social media post. There’s no need to ask Boone why he batted Trent Grisham leadoff in an elimination game. We know it’s because he has no idea what he’s doing and hasn’t since the day he was introduced as the manager nine years ago. There’s no need to ask Cashman anything because he’s a Steinbrenner in everything but name and he will hold his position for as long as he wants.

If you want to continue to be a Yankees fan, you need to accept that Boone is going to be in his position for a 10th year. You also need to accept that Cashman is going to be the general manager until he no longer wants to be, and when he no longer wants to be, he will choose his successor for the Steinbrenners, so they don’t have to do any work. You need to accept that the Yankees will continue to operate as if they are smarter than everyone and every team. You need to accept that they care more about the consecutive-season winning streak than they do about winning in October. Only then can you accept that being a Yankees fan doesn’t mean what it used to mean.

The pinstripes are no longer intimidating and the interlocking NY is now just another logo. Yankee Stadium isn’t some hallowed ground where the opposition’s postseason dreams die. It’s baseball’s version of a party hall or wedding venue that the opposition uses to celebrate the Yankees’ demise. The Yankees’ victory song has become the victory song for whichever team eliminates them. John Sterling’s “Theeeeeeeeee Yankees win!” has been turned into a punchline for the opposition’s Dominican star to repeat on national TV while drinking champagne inside the Yankees’ home. The Yankees aren’t scary. They’re a joke.

With each passing year, the championship drought gets a little longer and the brand power fades a little more. It’s been 17 years since the Yankees last won the World Series. Their one appearance in the Fall Classic during that time was such a humiliating spectacle that they would have been better off being eliminated in an earlier round. But they weren’t eliminated in an earlier round because they only played AL Central teams on their way to the pennant — the only way they can win a pennant with this roster under this regime. Despite being equipped with the best starting rotation in the majors, they were unable to win a game in the ALDS against a non-AL Central opponent. They were unable to hold a lead for a single pitch, batter or inning. The same team playing the same style that always ends their season early did so again, and no one should expect anything different next season.

A year from now Yankees fans will be waiting for the team’s annual end-of-the-season press conference while people employed and associated with the team and anyone who covers the team beg the organization to make a change. Nothing is going to change in the front office this winter. Nothing will change in the dugout. Nothing will change in the clubhouse. And because of all that, nothing will change in October. The Yankees don’t need to hold an end-of-the-season press conference to tell everyone what we already know.