NEW YORK, NY — What’s going on here? I refer again to words of the late New York sports columnist Dick Young.

And this time in an attempt to answer as to why the Yankees failed again in defense of manager Aaron Boone. 

A week-plus removed from Tampa Bay’s three-game sweep of the Yankees in the American League Division Series and there is uncertainty regarding the status of Boone’s job. 

Junior Caminero breaks out the broom for a Rays sweep 🧹 pic.twitter.com/iIPtknS6Rf

— MLB (@MLB) October 8, 2026

The usual season ending Q&A media session with general manager Brian Cashman, Boone and potentially owner Hal Steinbrenner is still on hold. Until then, the answers of what went wrong as well as the future of Boone and even Cashman are constant storylines.

To begin, the Yankees need to restructure and it will have to come at a rapid pace. Maybe minutes after the final pitch of the World Series later this month due to that December 1st lockout imposed by owners to players towards a new CBA looming. Then again, the two parties are not at the bargaining table yet and when they meet issues of a salary cap will be discussed which could create a 2027 season to be in the balance.

But first, the issue of a Yankees manager who is signed through 2027. An extension is also in the balance for Boone, realizing each of his predecessors Joe Torre and Joe Girardi fulfilled 10 years before he was hired. Then again, it has been a Yankees theme of retaining a manager long-term. A contrast of the actions from late owner George Steinbrenner, one being his temperament to seek rapid change when the Yankees failed with expectations to win.

With their postseason ending in the ALDS at the hands of the Rays on a sweep (3-0) after sweeping the Red Sox in the AL Wild Card Series (2-0), the Yankees find themselves looking for answers for 2027 and beyond – Image Credit: Alan Bautista/Latino Sports

Remember the soap opera drama with the late Billy Martin, Bob Lemon, Dick Howser and Lou Pinella? Steinbrenner would hire and fire, back-and-forth a manager gone. Back-and-forth the carousel of managers in the Yankees dugout and different philosophies, though loyalty with George was important. The leader of his franchise to him had to win.

Different, though with the new regime of his son Hal, and Cashman, with longevity in the Bronx. Cashman is Hal’s guy and always will be, yet he is the GM and the architect of this failure. And a lot of it is from roster construction and their reliance on analytics despite having a $341 million team payroll, the third highest among teams in MLB this season. 

Regardless of outcomes the past few years, ugly with Dodgers (2024), Blue Jays (2025), and Rays (2026) celebrating a championship, AL pennant, and ALDS victory on their home field, respectively, the signal was for the Yankees to institute change. 

Whether that be removing Cashman or Boone, the leadership remained.

Yankees general manager Brian Cashman will once again have a busy offseason with this winter including the current Collective Bargaining Agreement between MLB team owners and the MLBPA expiring on December 1st – Image Credit: Bill Menzel/Latino Sports

And as an observer with some clarity of the situation, both are expected to return in 2027, whether it be a lost season or abbreviated due to the impending lockout. It’s frustrating to the Yankees hierarchy and a fan base that has seen Cashman constructed teams with expectations without a World Series championship since 2009—the first year in their new stadium across the street from the old historic ballpark. 

That 28th World Series championship and lifting the Commissioner’s Trophy is elusive.

Yet Cashman with all the resources and top lieutenants regarded as such in baseball have failed. The Yankees’ dependency on the home run ball, errors and injuries were too prevalent. And they were not constructed as younger and athletic—two key components to a winning team with the third highest payroll.

Need I say, it’s about winning in New York. The Yankees don’t fail almost every year with being a part of postseason baseball, but rather by not finding a way or assembling a properly constructed roster to reach the finish line.

Aaron Judge was sidelined for the Yankees’ 2026 AL Wild Card Series vs. Boston and ALDS vs. Tampa Bay due to a moderate right calf strain – Image Credit: Bill Menzel/Latino Sports

Anything below a World Series championship is not an accomplishment based on Yankees standards. Standards that Aaron Judge, the captain commented on in a solemn clubhouse last week. 

“There’s a standard to winning a championship,” he said. “It’s black and white. There’s no gray area.”

And about that previous “running it back” quote, it can’t apply to restructuring whenever spring training 2027 commences.

The Yankees in 2027 are expected to have a much a different look up and down the roster, but time will tell on just how much – Image Credit: Bill Menzel/Latino Sports

Instead, the Yankees will eventually move on, and it will be again in the hands of Cashman. Younger with Ben Rice, Spencer Jones, Anthony Volpe, the assumed AL Cy Young Award winner Cam Schlittler, and George Lombard Jr. 

Also better without re-signing Jazz Chisholm Jr. and Trent Grisham. A run it back mantra for the bullpen perhaps by re-signing a revived Paul Blackburn and closer David Bednar (35 saves in 39 opportunities this year)—two of Cashman’s best moves the past two years. And eat the remaining $29 million contract of the constantly injured Giancarlo Stanton. 

Additionally, the hope is Judge, who turns 35 this coming April, will be healthy and return to his standards. There is that need for a right-handed catcher in the lineup as well.

The Yankees are confident that Aaron Judge will return back to his complete MVP form although the superstar is turning 35 this coming April – Image Credit: Bill Menzel/Latino Sports

Easier said than done, the free agency period will be rapid and busy. The lockout will push a deadline for some more than others with roster changes and salary structure. Younger and more athletic is a must, with the ability to play small ball, something the Rays and Brewers, even the Guardians have displayed in their march towards a World Series championship.

Yes, it’s up to Cashman. He’s staying unless there are changes in philosophy with him and the owner. Don’t expect that to happen.

Boone is on watch, but I don’t expect a change. He knows the roster complexion and changing managers with a lockout imminent does not help in a restructure or said retool. As much as Yankees fans continue to place blame on the manager, is it his fault for the failure?

Remember what I stated earlier, management embellishes longevity and consistency. Boone has met that criteria. And a manager is as good as his players presented, like the “Core Four” under Torre and those repeated World Series championships in the old ballpark.

All things considered with injuries piling on, Yankees manager Aaron Boone did a stellar job this season in navigating his club to a 93-68 record, which was good for the top AL Wild Card spot – Image Credit: Bill Menzel/Latino Sports

Boone, and I will not always agree, maneuvered the lineup and had to scramble and juggle with the constant injuries and call-ups from Triple-A Scranton this year. A lineup presented to him from that deep analytical department. Sometimes it worked, but numerous times it failed and that irked many fans of the pinstripes.

Yes, José Caballero in the lineup during the ALDS vs. Tampa Bay could have made a difference with his long at-bats, speed, and defensive ability at various positions.

But the numbers that define baseball instead had Chisholm out there, who was not productive and prone to costly errors.

José Caballero has played a major impact for the Yankees ever since arriving to the Bronx in the summer of 2025 prior to MLB’s trade deadline on a trade with the Rays – Image Credit: Ernesto Diaz/Latino Sports

Boone is not the culprit, perhaps coaching changes are needed. The Yankees at-bats contain too many first pitch swings. Too many swings and misses and lack of contact. Boone doesn’t take the field or step up to the plate. Pitching though is not a need of the Yankees, it’s an asset. Though all being one year older in 2027 could result in them in the market for another starter or arm in the ‘pen.

Players in the clubhouse speak highly about their manager, perhaps Boone needs to be more outspoken about the mistakes, inconsistency, and not be as repetitive with positives in his postgame comments.

Then again, Boone is that low level type exception of course with his record amount of umpire ejections that are showcased.

The expectation in the Bronx is the Yankees, still in search for their first World Series championship title since 2009, will officially start back up in their quest as soon as MLB’s World Series concludes – Image Credit: Bill Menzel/Latino Sports

Regardless, the Yankees are no closer to winning a World Series than they were the year before, or when they last got there in a humiliating loss to the Dodgers in 2024. There is a need to change the roster up and leaving Boone in place is a start as much as fans believe differently.

Cashman will stay, loyalty again is a factor. The moves to change the standards have to be different. 

The Yankees complexion awaits with so many questions as to what went wrong again.

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