After another October disappointment against the Toronto Blue Jays, the New York Yankees face a pivotal offseason to address core issues from a faltering offense to uncertain leadership, marking a crucial juncture for the franchise’s championship aspirations.
The New York Yankees‘ postseason journey ended not with a bang, but with a disheartening whimper in the ALDS against their division rivals, the Toronto Blue Jays. While the 4-2 series defeat wasn’t the “total embarrassment” some might associate with the 2024 World Series, it was undoubtedly a significant disappointment for a franchise perpetually burdened by “supersonic expectations.” As the Yankees’ World Series drought stretches to a painful 16 years, the focus immediately shifts to a winter of tough decisions and strategic re-evaluation.
The series revealed a Blue Jays team that was simply better, outplaying the Yankees in most facets of the game. Despite a high-profile error from Jazz Chisholm Jr. in Game 4, it wasn’t the defining mistake that swung the series. Toronto, in fact, made more errors overall. Even a signature October moment from superstar Aaron Judge couldn’t tip the scales in New York’s favor. The narrative quickly turned from what went wrong in individual plays to systemic issues within the organization.
The blame for the early exit is multifaceted. Three of New York’s four starters—Luis Gil, Max Fried, and Carlos Rodón—delivered “stinkers,” combining to allow 15 runs across just eight innings. This capitulation was particularly unexpected given the rotation had been a relative strength all year, even after losing ace Gerrit Cole to Tommy John surgery in March. Offensively, the team outside of Aaron Judge struggled immensely, posting a paltry .179/.246/.304 slash line. Key culprits included Chisholm (2-for-14), leadoff man Trent Grisham (2-for-17), and young slugger Ben Rice (2-for-11). However, no one struggled more acutely than shortstop Anthony Volpe, who finished the series 1-for-15 with 11 strikeouts.
Despite these struggles, some areas did shine. The bullpen, initially considered a potential Achilles’ heel, stepped up admirably. Rookie hurler Cam Schlittler also impressed, providing a glimmer of hope for the future. Yet, their efforts, alongside Judge’s consistent performance, were ultimately not enough to prevent another disappointing October. As the Yankees stare down a “ringless winter,” the organization faces five big questions that will shape its direction for years to come, as extensively analyzed by Yahoo Sports.
Will there be any major changes in leadership?
For a franchise that often appears to prioritize stability, significant changes in leadership seem unlikely. Owner Hal Steinbrenner has maintained a consistent approach since taking control in 2008, having only one general manager in Brian Cashman during his tenure. Cashman’s impressive track record, including 22 playoff appearances in 27 years, is highly valued, suggesting his position is secure. Manager Aaron Boone also appears safe, confirming at the post-Game 4 press conference that he is under contract and expects to manage in 2026. While he faces criticism for in-game decisions, his ability to manage a clubhouse filled with stars in a demanding media market draws considerable praise from the organization.
Which free agents are leaving?
The Yankees have a substantial list of players entering unrestricted free agency, including Trent Grisham, veteran first baseman Paul Goldschmidt, utility man Amed Rosario, bench outfielder Austin Slater, high-leverage relievers Luke Weaver and Devin Williams, and depth arms Paul Blackburn and Ryan Yarbrough. Outfielder Cody Bellinger, a key contributor in 2025, is widely expected to exercise the opt-out clause in his $25 million contract for next season, as reported by Yahoo Sports. The team is also expected to activate the $3 million option for lefty reliever Tim Hill, while declining the $5 million option for oft-injured reliever Jonathan Loáisiga.
Financially, the Yankees will have considerable flexibility. Approximately $30 million in dead money (from players like Aaron Hicks, Marcus Stroman, and JT Brubaker) is coming off the books, alongside the roughly $95 million paid to impending free agents. This provides New York with about $125 million to work with, though arbitration raises for younger players such as Jazz Chisholm Jr., Anthony Volpe, David Bednar, and Fernando Cruz will reduce that figure. Given the increasingly left-handed nature of the lineup, it’s difficult to see both Grisham and Bellinger returning. Bellinger, despite commanding a higher price, seems the more likely of the two. Similarly, it’s improbable that both Williams and Weaver will be back, as the Yankees have historically avoided shelling out big money for free-agent relievers. Goldschmidt is also a strong candidate to depart, paving the way for Ben Rice to become the everyday first baseman.
Which free agents make sense to add?
The Yankees will likely explore the market for impact players, but with an eye on fit and long-term strategy. While they might “dip their toes” into the Kyle Tucker discussions, a full commitment seems unlikely. Alex Bregman, potentially opting out of his contract with Boston, presents an intriguing option as a high-contact, right-handed bat, though his arrival would necessitate a significant defensive reshuffling. The starting rotation, with Max Fried, Carlos Rodón, and Cam Schlittler set to lead, and Gerrit Cole expected back mid-year, feels relatively stable.
Rumors surrounding Pete Alonso will undoubtedly surface, but committing long-term to another first baseman makes little sense with Ben Rice in the fold. Kyle Schwarber, primarily a designated hitter at this stage of his career, is also an improbable fit given Giancarlo Stanton’s presence. Japanese slugger Munetaka Murakami, at just 26 years old and capable of playing both corner infield spots, could garner attention. Bo Bichette, known for his hitting prowess, would be a significant offensive boost, but his defensive limitations at shortstop would be a notable downgrade if the team decides to move on from Volpe.
Do they stick with Volpe?
Anthony Volpe’s 2025 season was, by all accounts, dreadful. His offensive numbers regressed, and his defense appeared out-of-sync for much of the year. While his glovework improved down the stretch, his performance at the plate in the ALDS was particularly alarming. Over the years, the Yankees made a deliberate choice to pass on a string of high-profile free-agent shortstops, including Carlos Correa, Corey Seager, Trea Turner, Willy Adames, Trevor Story, and Dansby Swanson, all due to their unwavering faith in their homegrown talent. That faith is now undeniably waning. Whether Volpe enters spring training as the undisputed starting shortstop will be one of the most closely watched storylines of the upcoming winter, heavily debated within the fan community.
Do they leave a runway for Jasson Dominguez?
Jasson Dominguez, known to fans as “The Martian,” completed his first full season in the big leagues in 2025 with a mixed bag of results. He remained healthy, a positive sign, but his offensive output settled at a league-average batting line, coupled with concerning defensive numbers in the outfield. Consequently, his playing time dwindled as the season progressed; he started only six games in September and played a full nine innings just once. His sole contribution in October was a pinch-hit double in the ninth inning of Game 4. At just 22 years old, the switch-hitter still possesses immense potential, but the Yankees must provide him with consistent playing time for him to develop into a game-changing force. However, contending teams like New York often hesitate to risk everyday roles on “flawed youngsters” who require significant development time. The question of whether there’s a clear path for “The Martian” in New York’s competitive lineup remains a significant point of discussion among the fanbase.
