The curtain fell early on the Yankees’ 2025 championship aspirations, leaving the organization at a crossroads that feels all too familiar. Sixteen years have passed since the Yankees last stood atop the baseball world, their floats rolling through the Canyon of Heroes. As they turn the page to a new season, here are five of the biggest questions that will define their direction. 1. What is the plan for Aaron Judge’s elbow?
Ahead of the American League Wild Card Series against the Red Sox, Aaron Boone waved away questions about Judge’s past postseason performance, predicting that his captain “will have one where he goes crazy.” The world saw exactly what that meant when Judge collected 13 hits in 26 at-bats (.500), including a signature October moment, his three-run homer that clanged off the left-field foul pole to tie AL Division Series Game 3 against the Blue Jays. |
Unfortunately for Judge and the Yankees, we’ll never know how he would have continued to perform if they had advanced to the next rounds. Now the focus shifts to Judge’s elbow. He sustained a right flexor strain making a throw in late July, and he had an accelerated in-season rehab that allowed him to return to outfield play in September. Judge anticipated opponents would test his arm, and though he was clearly compromised, he did uncork a few strong throws in October. Judge said after Game 4 that “we’ll do some work on it and get it right.” When asked if that could include surgery, he replied: “I’m not a doctor. I don’t know.” The most likely outcome is that Judge will try to avoid surgery, understanding that a procedure could cost significant time. |
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2. Will Cody Bellinger return? What about other free agents?
Bellinger will opt out of the final year of his contract, which would have paid him $25 million in 2026. After a strong season (.272/.334/.480, 29 homers, 98 RBIs), the 30-year-old has said his priority is to play for a contender, a stance that could keep the Yankees in the mix. “I had an unbelievable time putting on this uniform -- Yankee Stadium, the fans, the organization, the culture that these guys have created in this locker room,” Bellinger said. “And it really is special.” |
Trent Grisham transformed into an everyday contributor; his defense and left-handed power project to make him an appealing target for multiple clubs. Paul Goldschmidt says he plans to continue playing in 2026, while Devin Williams said he’d “definitely” be open to a reunion. “At first it was a challenge. But I've grown to love being here,” Williams said. Other potential departures include Luke Weaver, Jonathan Loáisiga, Ryan Yarbrough, Paul Blackburn and Amed Rosario. 3. What does the future look like at shortstop?
Anthony Volpe called the ALDS loss “brutal,” noting, “I’m kind of in shock.” As the offseason begins, the Yankees must ask hard questions about him. It has been three years since they anointed Volpe as their starting shortstop, and by any measure, the 24-year-old’s progress has stalled. Volpe said his takeaway of the season was that there is “a lot of work to be done.” And though some of that may be due to the partially torn left labrum he played through, that might not stop the Yankees from exploring other options. |
One year after belting a World Series grand slam, Volpe was a nonfactor in the ALDS, hearing boos as he went 1-for-15 (.067) with 11 strikeouts. José Caballero picked up some playing time in September, and the Yankees could stage a spring competition -- perhaps even bringing in other candidates. Volpe didn’t rule out surgery, saying he expected to keep playing another month before reassessing the shoulder. “I had a really good relationship with the training staff, and they trusted me. I trusted them,” Volpe said. “We grinded the whole way. I could've done a lot better.” 4. What will the outfield look like?
With Bellinger and Grisham set to test free agency, the Yankees must consider their outfield alignment. Jasson Domínguez’s pinch-hit double in Game 4 was his first at-bat since Sept. 21 -- a surprising absence for a player once billed as part of the club’s future. Do the Yankees really believe Domínguez is part of the solution moving forward? And if not, how much is his development being hurt by spending so much time on the bench? |
The Yankees also have Spencer Jones -- their No. 4 prospect per MLB Pipeline -- banging on the door after he slashed .274/.362/.571 with 35 homers and 80 RBIs in 116 Minor League games. Yankees general manager Brian Cashman has said that if Jones were in another organization, he might have already been promoted. “He’s earned his way to be up here, but there’s no spot to put him right now,” Cashman told MLB Network Radio on SiriusXM in September. “So let’s get through our winter, see what that looks like and get him into Spring Training. But he should take a bow; he has made his adjustments, he’s learned and grown and showed he’s capable of fighting through things.” 5. Are changes necessary in leadership?
The Hal Steinbrenner Yankees prize continuity. On the day Boone was hired, Cashman said his expectation was that they would continue with the same field manager for at least a decade, just as they did with Joe Torre (1996-2007) and Joe Girardi (2008-17). That has nearly proven true, with one major caveat: Torre and Girardi delivered championships. Boone has not. If the Yankees’ last trophy were a human, it could register for a New York State driver’s permit. “I'm confident we'll break through, and I have been every year,” Boone said. “I believe in so many of the people in that room. That hasn't changed. The fire hasn't changed. It's hard to win the World Series. I’ve been chasing it all my life.” |
Boone is under contract for two more years and expects to return. But what about the rest of the front office -- are changes necessary in personnel, analytics and roster philosophy to change the outcome? Many believe that is overdue. After the 2023 season, there was a lot of discussion about an “audit” of the club’s operations. Much of that was misconstrued by media reports: It was essentially the Yankees taking a look at how an outside firm, Zelus, conducted its operations -- not the other way around. Cashman is already the longest-serving GM in Yankees history, having surpassed Ed Barrow in 2022. His contract expires in 2026, and he has been noncommittal about his future beyond this deal. It’s possible New York will look to elevate Cashman into an advisory role at some point, similar to the late Gene Michael, but that conversation has not yet occurred. |
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