The World Series

Now that the season is over for our boys in pinstripes, the ugly reality of this once precious sports franchise is undeniably rotten. The Yankees failed to reach the World Series this season after their 2024 World Series appearance against the L.A. Dodgers. The Yankees crashed back down to earth after beating the Boston Red Sox in the Wild Card Series. Facing the A.L. East division winners, the Toronto Blue Jays, the Yankees realized the Jays are really good at baseball.

Game 3 of the World Series is proof that the Blue Jays may be the only team that can keep up with the wealthiest team in baseball, the L.A. Dodgers. Toronto’s GM, Ross Atkins, deserves plenty of credit for building a roster of this caliber. The Blue Jays’ payroll is ranked 5th this season with $255,380,936 invested in players who perform as expected. The Blue Jays have built a solid lineup around star player Vladimir Guerrero Jr. Guerrero’s postseason dominance has increasingly improved each game. Despite facing a difficult L.A. Dodgers’ roster in the World Series, the Blue Jays’ Ross Atkins is confident in the team he’s built. 

Aaron Judge

The Jays are not built on ideas of the “wait and see approach.” It’s not built on hopes that players past their prime can resurrect prior success. These guys are hungry to win. Their performances this season, as well as in the postseason, speak for themselves. Fans and baseball analysts see the inception of a Blue Jays team that is built for long-term success.

Most importantly, the Jays are a team that plays the game of baseball with passion and focus. As I watched my New York Yankees begin to slowly crumble in the A.L. Division series with Toronto, it’s clear that Aaron Judge’s loyalty to the Yankees is admirable. Aaron Judge is 33 years old, and regardless of his age, the guy’s offensive stat line is insanely greater than MLB’s greatest hitters in history. I believe Judge is wasting his precious years with the Yankees despite obtaining individual accolades for performance. Judge could’ve easily signed with the San Francisco Giants during his free agency to play with young players eager to win.

Honoroble Judge

Judge left hundreds of millions more on the table in comparison to Stienbrenner’s offer. Judge is loyal to Hal, and is rewarded with another losing season. Yet, Brian Cashman and Hal Steinbrenner are intentionally clueless as well as misguided in their efforts to complement Judge’s presence. The Yankees continue relying on a cast of employees whose expertise and experience are no longer relevant in today’s environment.

Cashman’s Solution

The practice of surrounding Aaron Judge with mediocre talent has failed continuously for Cashman. The attempts from the Yankees’ front office and analytics department is middling. Substituting A Graded players with B’s and C’s is almost as bad as Cashman’s repeated quotes to the media. More embarrassing is Cashman’s similar approach in obtaining players, which mimics Brad Pitt’s “Moneyball” film. In one scene, the Oakland Athletics’ master plan is replacing a star-studded team with cheaper options who produce similar offensive stats.

Money Ball

The film is centered on the Athletics’ true-life events. The film’s analytical philosophy of success has influenced vulnerable minds such as Brian Cashman’s. If we analyze the film Money Ball and its claims of success, then baseball has become a predictable sport. The plot of the film overly simplifies replacing players like Jason Giambi with another player whose projections can imitate Giambi’s stats for a 1/4 of his price. If the anayltics are correct then there’s no need for Giambi, right?. The problem with this baseball ideology is these are flesh-and-blood individuals playing the sport, not AI robots or a humanoid. What’s even more comical, since 2015, the Oakland Athletics have finished the 8 of their last 11 seasons in 4th or 5th place in their division.

This moneyball approach by the Yankees and other MLB teams has become a staple in the sport. It exposes the low level of intelligence team owners and GMs are endowed with. Perhaps it shows their high level of intelligence in sourcing a financial solution. Establishing greater personal wealth rather than reinvesting profits into building an adequate roster. It’s not coincidential many MLB teams have adopted this method of business. Many have chosen a hybrid approach that offers a balanced outlook that focuses on rational thinking. 

Yes Man

The heart of a winner is irreplaceable. Athletes like Aaron Judge, Shohei Ohtani, and Vladdy Guerrero are perfect examples of that. The basis of their high salaries is not granted because of their nice smiles and light-hearted personalities. It’s because these players excel mentally and physically on the field. Expecting Aaron Judge to score every run for the Yankees is unrealistic, but so is Brian Cashman’s World Series expectations with a group of washed, spoiled, and mid-tier cast of players. What’s worse is the front office’s blind confidence in managerial decisions by Aaron Boone. Boone’s antics have grown tiresome with his constant rotation of players in any game. Boone is possibly the perfect puppet Cashman has control over. Boone is Brian Cashman’s “YES” man, and finding another manager to fill Boone’s role will be difficult from that perspective. 

"I think he's a good manager. He's one of the better managers. If he was out there right now, he'd get a job rather quickly.

Because of our environment, he's someone that can be second-guessed ten million times over. I don't care who you put in that, it would be the same with… pic.twitter.com/ADDRDVnNtB

— Yankees Videos (@snyyankees) October 16, 2025

The Business

My greatest fear is that players such as Aaron Judge, Ben Rice, or Cam Schlittler will never taste the glory of winning the World Series. The dangerous truth about the New York Yankees is their management and ownership outlook under Hal Steinbrenner’s control. The Yankees use valuable assets such as their 27 World Series championships and brand-name players like Aaron Judge to simply give the illusion they are trying to rejuvenate their baseball relevance. The die-hard Yankees fans can clearly see that this roster is not championship quality. Brian Cashman’s blatant choice of talent in building this team year after year has become insulting to many fans.

The usual parade of using players like Gerrit Cole and Aaron Jude as circus monkeys to boost their revenue and profit is incredibly distasteful to witness. The Yankees are still the beloved baseball franchise we’ve grown to know. The rich history will continue to stand the test of time. Yankees fans should temper their championship hopes unless there is a meaningful and logical process to building a proper team.