The 2025-2026 offseason has been a curious one, to say the least. To say that the “Hot Stove” period has been as cold as the polar ice caps would be a massive understatement. Allegorically, the movement of the offseason can only be categorized as a tortoise trapped in molasses-covered quicksand. Yet, for as slow as the offseason has been around all of Major League Baseball, one team that’s always expected to be heavily involved in the market has found itself frozen in time. The New York Yankees are losing grip of their reality. And time is of the essence if the Yankees are to secure their legacy and save their 2026 season.

WHAT’S THE DIRECTION?

It seems for the Yankees, this offseason was about stating that the lackluster ending of 2025 was nothing more than a fluke. That the “crapshoot” of the postseason and their subsequent flushing by the Toronto Blue Jays shouldn’t diminish the “success” of the 2025. However, anyone with two spare brain cells to rub together can examine the Yankees and see their flaws. And those flaws are from more than just a season ago. The failures of this organization date back to 2010. Thus, the failures of this organization have largely been overlooked by ownership and the front office. Seemingly, the only ones asking the question about what is being done to correct the misdirection, misdiagnosis, misalignment, and mismanagement of this team are the fans.

The major question on the mind of Yankee fans this offseason, as several quality, albeit lower-level players have come off the board, is what is the direction of this team for the upcoming 2026 season? It seems as if the Yanks’ front office is solely looking at bringing back Cody Bellinger, but only at their number. Offering Trent Grisham the $22 million qualifying offer has come to bite the Yankees in a way Mike Tyson would be proud of, in jest, of course. However, the Yankees front office’s belief, or some would say their over-reliance on analytics, has diminished their ability to see what’s right in front of them. Leading fans again to question, what is the direction of this team?

NATURE VS. NURTURE OR BETTER YET DEVELOPMENT VS. DETRIMENT

Many fans have pleaded, begged, downright groveled online for the benching (or banishment at this point) of starting shortstop Anthony Volpe. In the same breath, they have pleaded, begged, and downright groveled online for the opportunity to give Jasson Dominguez the full run of opportunity and the proverbial leash that Volpe has received in his three-year tenure in the Major Leagues. Dominguez was viewed as a much better overall prospect, yet J-Dom has not been given the keys to drive his potential future with the club.

The culture created within the Yankees organization has been scrutinized and commented on by many baseball insiders and pundits. But it’s also been called out by former players, most recently by Clint Frazier. In some ways, the culture created has empowered certain players (ie, Anthony Volpe) while other players are shunned into obscurity, like Frazier, J-Dom, Deivi Garcia, Manny Banuelos, among others.

Certain aspects of the Yankees’ development tree have matured wonderfully. For example, the pitching lab for New York is rivaled by only the best in the game. While the catching development is the envy of the league. However, the offensive core of the team’s development structure had been abysmal. But wait…what about Aaron Judge? He’s arguably the best hitter in the game today. Aaron Judge sought help from outside of the organization to become the hitter that he is today. And no one brought up and drafted by the organization has come close to replicating the same level of offensive contributions as other organizations have developed. The culture core of the New York Yankees stops any and all clubhouse infighting that could present issues, like the rumored issues across town for the Mets. However, the culture is also one that doesn’t help develop positive offensive talents. There is a rigidity to the Yankees’ philosophy when it comes to offense; it’s Bronx Bombers or bust. Being a home run-hitting team works in the macro (ie, over the course of the 162-game season). However, it isn’t a philosophy that lends itself to success in the micro (ie, a 5-7 game postseason series). For the Yankees, the detrimental development structure needs a significant overhaul in philosophy. Yet it doesn’t stop there.

It’s Not Just a Money Thing Either

Most Yankee fans will just say that Hal Steinbrenner (Yankees Managing Partner) is just being cheap. However, that statement is both inaccurate and misleading. The truth is that the Yankees are spending money at the top tier of the baseball world. In 2025, the Yankees (*$303.3 Million) ranked third in team payroll after the Los Angeles Dodgers (*$346.9 Million)and the crosstown New York Mets (*$338.52 Million) (*according to Cot’sBaseballContracts.com). Hal Steinbrenner has authorized and allocated a tremendous payroll for the Yankees to try and be successful. And depending upon how you define success, the Bronx Bombers have been a rousing success. If the goal is to field a “competitive-looking” team that generates a profit for the Yankee shareholders, then New York has been wildly successful. However, if you measure success by the ruler of Hal’s father, George M Steinbrenner III, then the true measure of organizational success is winning championships. And the Yankees have failed at that goal for the last sixteen seasons. New York is just two seasons away from tying the longest stretch without a championship since someone with the last name Steinbrenner owned the team.

So that’s the biggest determining factor, and the biggest difference in the mental philosophy of this current iteration in the Bronx. The definition of how success is truly measured and achieved has changed under the current regime. For the ownership and front office, the goal appears to be to maximize the appearance of desire to “win”. While in reality, the goalpost for success is now measured by the thickness of the wallets of their shareholders.

It’s All About Putting on a Good Show

As a franchise, the New York Yankees were once the most feared and respected team in baseball. There was a mystique and aura about them that lived up to the hype. (Despite the dancers that Curt Schilling claimed them to be years ago.) However, since the fall of 2004, the Yankees have not been the same team. New York has gone through several changes in the way the team has performed its act for the fanbase. We all recall the last time the Yankees hoisted the World Series trophy and banner back in 2009. And since then, the team has endured countless losing seasons despite their winning regular-season record.

For fans of the New York Yankees, winning isn’t measured in regular-season victories. Winning isn’t measured by the number of tickets sold or the seemingly endless quantities of merchandise moved with the iconic NY symbol on it. There is a simple and basic principle of success, an easy and childlike way to define winning. Are you the last team standing when the dust falls and the smoke clears? Is it yours that’s the final team shaking hands and taking pictures on the field in front of the Commissioner’s trophy? If you are not, and the Yanks have not been that team for sixteen long seasons, then you are not the best franchise. Then you are not able to say that you’ve had a successful season. And you can not sit idly by, and then this glacial offseason continues without making any noticeable improvements to your team.

The 2025 Yankees were not good enough to win, and “running it back” with the same crew will yield worse results than last season. It is time for the New York Yankees to remember who they are, who they are required to be in the lexicon of baseball history. The Yankees are at their best and baseball is at its best when the Yankees are the “Evil Empire” and the villains of the baseball world. The time is now for the Yankees to strike. No longer can New York sit by and let the rest of the division pass them by, despite what the early betting odds and prognosticators’ projections say about them. Time is of the essence for the New York Yankees!