The New York Yankees' offseason has kicked off much earlier than anyone anticipated, thanks to their playoff exit at the hands of the Toronto Blue Jays. The Blue Jays clinched Game 4 of the American League Division Series with a 5-2 victory, bringing the Yankees’ postseason campaign to an abrupt end and stirring emotions with a raucous celebration right on the Yankees' home turf. This unexpected early departure has left the Yankees’ fanbase simmering with frustration and disbelief — especially after the high hopes following their run to the 2024 World Series. And this is the part most people miss: despite another spectacular season from superstar Aaron Judge, the team couldn’t capitalize, leaving many to wonder how such a promising year ended in disappointment.
General Manager Brian Cashman faces pressing questions as he prepares for the offseason ahead. Here are three of the biggest challenges looming over the Yankees’ operations:
What lies ahead for Aaron Boone?
Aaron Boone remains the head coach with two years left on his contract, and it's widely expected he will remain in place. The backlash against Boone could have been deafening if the Yankees had lost in earlier rounds or been swept by the Blue Jays, but public pressure has notably cooled. The organization appears inclined to follow the familiar path of continuity, sticking with an operational model based on stability.
To put it bluntly, Boone’s tenure hasn’t produced a championship — his record stands at zero titles in eight years managing the Yankees. If the franchise had foreseen this outcome before hiring him, they might have considered other candidates or retained Joe Girardi. Yet, even with this postseason letdown, there are no indications from Cashman that a change is imminent. In fact, as of mid-August, Cashman praised Boone’s leadership through the team's summer struggles, highlighting the unique skill set required to handle a large roster under intense pressure in New York's high-profile environment.
Boone’s character and leadership have earned him strong support from key figures like owner Hal Steinbrenner and star player Aaron Judge, both of whom have publicly backed him. Despite some rough patches during the season, the Yankees still finished with an impressive 94-68 record, tying for the best in the American League. Boone’s regular-season winning percentage (.584) ranks second among active managers, just behind Dave Roberts of the Los Angeles Dodgers (.621). With two years left on his deal, Boone could reach a decade at the helm, matching the tenures of predecessors Joe Torre and Girardi. Notably, Cashman once expressed a desire to keep Boone for 10 more years, signaling a strong vote of confidence to stay the course.
Which free agents are likely to return?
This offseason presents critical decisions around eight Yankees players who are unrestricted free agents: Paul Blackburn, Paul Goldschmidt, Trent Grisham, Amed Rosario, Austin Slater, Luke Weaver, Devin Williams, and Ryan Yarbrough. Additionally, the team holds club options on Tim Hill and Jonathan Loáisiga, and there’s the notable case of Cody Bellinger, who has a $25 million player option he's expected to decline in search of a longer-term contract.
Some departures seem certain. Paul Goldschmidt won’t be offered a new deal, as the Yankees are committed to Ben Rice as the first baseman of the future. Austin Slater’s hamstring injury and poor performance likely shut the door on his return. After disappointing campaigns, it seems unlikely that Weaver and Williams will re-sign, especially since the Yankees traditionally avoid high-priced contracts for relievers. Yarbrough proved to be a respectable depth option, but his role does not extend beyond that.
That narrows the potential returnees down to Rosario, Blackburn, and Grisham. Rosario has been a repeated target as a valuable bench piece, and with José Caballero and a possible backup catcher like J.C. Escarra in the fold, keeping Rosario could come at the expense of a younger player like Oswaldo Cabrera, who might then face trade or reassignment.
Blackburn showed promise by significantly improving late in the season after the team adjusted his pitching style, leading some to hope he might be a savvy re-signing, similar to the surprise value they got from Weaver two years ago.
Grisham’s case is particularly intriguing. He had a career year with 34 home runs and a 129 weighted runs created plus (wRC+), ranking the second-best among primary center fielders this season. However, despite his age (29 next season) and standout performance, there’s risk in offering him a long-term deal. While his numbers suggest this season’s success wasn’t a mere fluke, his struggle against off-speed and breaking pitches and his below-average speed—especially critical in center field—raise questions about his future role and defensive position.
The Yankees might opt to tender Grisham a qualifying offer, a one-year, $22 million contract. Should he decline and test the free-agent market, his options could be limited due to the draft pick compensation attached to signing a player with a QO. If Grisham accepts the offer, it would provide the Yankees more time to evaluate promising prospects like Spencer Jones and Jasson Domínguez, who both aim to establish themselves at the major league level.
It’s expected the Yankees will pick up Tim Hill’s club option. Conversely, Jonathan Loáisiga is likely to be non-tendered following another injury-riddled season.
Will the Yankees pursue Cody Bellinger or Kyle Tucker?
The most heated offseason question revolves around how aggressively the Yankees will look to boost their roster. Boone has publicly stated that this season’s lineup was the strongest he’s ever managed.
Cody Bellinger played a pivotal role, delivering his best wins above replacement (fWAR) since his 2019 MVP campaign. His versatility in playing all three outfield spots and a pull-heavy hitting style help him overcome some striking contact quality issues. Represented by Scott Boras, Bellinger isn’t expected to accept a below-market, team-friendly offer. Yet, comparatively, he will be more affordable than Kyle Tucker—arguably the most sought-after free agent this offseason.
Tucker experienced a down year by his own high standards but still posted an impressive 136 wRC+ while with the Chicago Cubs. Half of his games being played at Yankee Stadium could elevate his performance, possibly positioning him as one of the game’s elite hitters. The catch? Tucker’s price tag could exceed Bellinger’s by as much as $200 million, presenting a significant financial hurdle. This might ultimately lead owner Hal Steinbrenner to view Bellinger as the more realistic and appealing option for the team’s future.
Here’s where it gets controversial: Would committing massive resources to a star like Tucker, regardless of cost, be a smarter move to push the Yankees back to championship contention? Or is prudence the wiser path, banking on affordable, versatile players and development from within? What do you think? Share your thoughts below—should the Yankees gamble big or stick to what they know?
