NEW YORK, NEW YORK – OCTOBER 08: Aaron Judge #99 of the New York Yankees walks off the field after the Toronto Blue Jays defeated the Yankees in game four of the American League Division Series at Yankee Stadium on October 08, 2025 in New York City. (Photo by Al Bello/Getty Images)
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The New York Yankees have become synonymous with postseason failure since 2010 while clinging to a World Series-or-bust mantra that has become farcical to fans and many throughout Major League Baseball. It’s a bitter pill to swallow given how the Yankees have won at least 90 regular season ball games 10 times since their last World Series victory in 2009 and are now spending more than $300 million annually on payroll. Let’s not forget nearly $278 million in Competitive Balance Tax penalties since 2010 according to the Associated Press and are expected to be a fourth-time payor under the current collective bargaining agreement this winter. October is no longer a month-long celebration that concludes with a World Series victory for the Yankees, but an observation of how a crown jewel franchise is blinded by its history which is affecting decisions regarding player development.
New York Yankees And Prime Years Of Aaron Judge
The problems plaguing the Yankees go well beyond the perceived front office influence on manager Aaron Boone’s decision-making in the dugout. It even surpasses outcries from disgruntled fans to fire senior vice president, general manager Brian Cashman and for the Steinbrenner family to sell the franchise based on the $8.2 billion valuation according to Forbes. The Yankees are wasting the prime years of right fielder Aaron Judge’s career as questions regarding organizational philosophies on hitting, pitching and defense are being called into question. Judge earns $40 million annually throughout the length of his nine-year contract, but his value in what he would have made in free agency for the 2025 season based on FanGraphs’ calculation of wins above replacement (WAR) was $81 million courtesy of a 10.1 WAR. According to Cot’s Baseball Contracts, there are six years remaining on the 33-year-old Judge’s contract totaling $240 million.
The Toronto Blue Jays enjoyed a champagne-soaked celebration at Yankee Stadium after winning their first postseason series since defeating the Texas Rangers in the 2016 American League Division Series. First baseman Vladimir Guerrero Jr. couldn’t help but join FOX Sports analyst David Ortiz in mocking the Yankees during a clubhouse interview while the Blue Jays played Frank Sinatra’s famous song, “New York, New York.” Even manager John Schneider seized the opportunity to antagonize his defeated adversaries given the aura of invincibility that accompanies the Yankees. Success for the Blue Jays has been built on three principles of player development: high contact approach to hitting, low strikeout percentage and stellar defense. Fans of a certain age recognize those principles as hallmarks of legendary Yankees first baseman Don Mattingly who happens to be the bench coach for the Blue Jays.
New York Yankees And Anthony Volpe Concerns
Shortstop Anthony Volpe has become a target of criticism. While 19 errors over 1,303.2 innings with a -5 fielding run value (FRV) will not put you in the upper echelon of shortstops within Major League Baseball, what are the Yankees doing to help the 24-year-old Volpe grow and learn from his experiences? Volpe has struggled with defensive positioning and confidence. It wasn’t until September that news surfaced how Volpe was dealing with a partially torn labrum in his left shoulder since May.
The bat slips out of New York Yankees Anthony Volpe’s (11) hands as he swings during the second inning of Game 3 of baseball’s American League Division Series, Tuesday, Oct. 7, 2025, in New York. (AP Photo/Frank Franklin II)
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The same conversation goes for 22-year-old Jasson Domínguez as he posted a -9 FRV over 793.0 innings in left field and an unflattering 26.8% strikeout percentage over 429 plate appearances. As both were once viewed as top-flight prospects, it is hard to discard young talent so flippantly given their combined 2025 contracts were valued at $1,653,300 according to Cot’s Baseball Contracts. Volpe is arbitration-eligible for the first time this offseason and Domínguez would like to play a prominent role in next year’s outfield given the potential departures of Cody Bellinger and Trent Grisham to free agency.
Besides the dilemmas regarding Volpe and Domínguez, what are the Yankees going to do when it comes to the development of pleasant surprises such as first baseman/catcher Ben Rice and right-handed pitcher Cam Schlittler? Rice needs to improve as a defender at first base if he wants to be an everyday ball player at the position. The Yankees also need to see offensive improvement in catcher Austin Wells amid strong defensive statistics as evident in an 11 FRV over 1,001.0 innings.
New York Yankees And Reunion With Cody Bellinger
Bellinger opted out of the final year of his contract in which he would have been paid $25 million ($5 million buyout) according to Cot’s Baseball Contracts. A reunion between Bellinger and the Yankees must be a top priority given his offensive contributions and defensive versatility. Grisham is a wild card as he earned $5 million for the 2025 season and could be extended a qualifying offer by the Yankees. However, are the Yankees willing to pay the estimated value of a qualifying offer being a one-year contract at $22 million? If extended, would Grisham be willing to sign a lucrative, but short-term contract after a career year in the Bronx?
NEW YORK, NEW YORK – OCTOBER 07: Jazz Chisholm Jr. #13 of the New York Yankees reacts after hitting a solo home run against the Toronto Blue Jays during the fifth inning in game three of the American League Division Series at Yankee Stadium on October 07, 2025 in the Bronx borough of New York City. (Photo by Ishika Samant/Getty Images)
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Second baseman Jazz Chisholm Jr. is entering his final year of arbitration eligibility before free agency next offseason. After earning $5.85 million for the 2025 season, do the Yankees envision the 27-year-old Chisholm Jr. as their second baseman of the present and future? If so, what does a development strategy look like for Chisholm Jr.? Miscues at second base and lapses in judgement have plagued Chisholm Jr. even after becoming only the third ball player in franchise history to have hit at least 30 home runs and steal 30 bases in the same season. In 851.0 innings at second base during the 2025 season, Chisholm Jr. posted a 5 FRV which ranked third among second basemen in Major League Baseball based on a minimum of 850.0 innings played at the position according to FanGraphs.
Will New York Yankees Pursue Munetaka Murakami?
The Yankees will be the first to tell you they aren’t a bank. However, expect them to pay close attention to Munetaka Murakami, a left-handed hitting corner infielder for the Tokyo Yakult Swallows of Nippon Professional Baseball (NPB) in Japan. An all-star on four occasions, the 25-year-old Murakami hit 246 home runs over eight seasons in NPB while winning two Central League Most Valuable Player Awards. While he possesses intriguing power, Murakami’s propensity to strike out is a concern as evident in a career 25.8% strikeout percentage according to Baseball-Reference. If he becomes available, Murakami will be subjected to Major League Baseball’s Japanese Posting System and would be a costly investment in terms of a contract and release fee.
Prestige will always accompany the New York Yankees, but that doesn’t mean a sense of entitlement is woven into the fabric of the uniform. The marketing strategies associated with selling the history and tradition of the franchise work well when it comes to memorabilia, merchandise and stadium tours. However, it’s hard to sell a championship pedigree every season to at least 3 million fans who attend ball games at Yankee Stadium and expect them to pay premium prices for a product that fails to deliver on that expectation. Radical change is not needed, but careful attention to player development is important given the current disconnect between messaging and results.