Five questions facing the Yankees this offseason
Yankees shortstop Anthony Volpe reacts after he strikes out in the second inning against the Toronto Blue Jays in Game 4 of the American League Division Series on Wednesday at Yankee Stadium. Credit: Newsday/J. Conrad Williams Jr.
1. Is the window closing on Aaron Judge’s chance to win a World Series?
The reigning and two-time American League MVP — with a shot to make it back-to-back wins next month — will turn a hard-to-believe 34 in April. The Yankees have made the postseason in eight of his nine full seasons, including the World Series last year, when they were steamrolled by a superior Dodgers team.
On the eve of this postseason, Aaron Boone had reason to say he felt better about this team going into the playoffs than any of his previous ones. From a top-to-bottom standpoint, it was the most complete roster and represented Judge’s best chance at a title since his rookie year in 2017. That club, managed by Joe Girardi, lost in seven games to the Astros in the ALCS (and led that series three games to two before dropping Games 6 and 7 in Houston).
Judge, as evidenced by this season, is still at the peak of his powers. But that time isn’t forever.
2. Will Anthony Volpe be the starting shortstop next season?
Volpe, 24, capped a miserable 2025 — his third season in the big leagues — with a dreadful performance against Toronto (1-for-15 with 11 strikeouts). He regressed offensively and defensively, something he would be the first to acknowledge even as Boone defended his shortstop in public.
Though there already are howls for hyped shortstop prospect George Lombard Jr. to be given a chance to win the job in spring training, that isn’t going to happen. Lombard, who turned 20 in June, stalled a bit this season after a quick promotion — which he earned — to Double-A Somerset. The Yankees, as well as rival scouts, don’t find Lombard’s struggles in Double-A to be especially relevant and believe he’ll be a big-leaguer, and a good one, soon. It just won’t be late March of next year as the Yankees’ starting shortstop.
As for Volpe, he heads into a critical offseason. Shortstop of the Yankees isn’t a lifetime appointment. After getting the tear in his left labrum addressed — likely with a procedure of some kind — it will be down to Tampa, where Volpe spends most of his offseason, to start preparing for the most important year of his career.
3. Which free agents will return in 2026?
The Yankees have a slew of them, a group that will include outfielder Trent Grisham, first baseman Paul Goldschmidt and relievers Devin Williams and Luke Weaver and also figures to include outfielder Cody Bellinger. After Wednesday’s loss, Bellinger all but said he will opt out of the final year of his contract, though he “absolutely” would be interested in a return to the Bronx. The feeling is mutual, and re-signing Bellinger, who excelled in all facets of the game in his first season in pinstripes, will be among the organization’s top priorities.
The Yankees, with some exceptions over the years (Aroldis Chapman, for one), generally don’t pay top dollar for relievers. That means, though nothing can be ruled out, Williams and Weaver are likely to get paid elsewhere. Ben Rice’s emergence makes Goldschmidt, a long shot to return anyway because of his age (38), a goner.
4. What version of Gerrit Cole will the Yankees get in 2026?
Cole, the 2024 AL Cy Young Award winner, was lost for the season in spring training after undergoing Tommy John surgery. His rehab, including the throwing program he began in August, has gone without incident, and the righthander has talked about being able to report in February and have a “normal” spring training. Still, Cole just turned 35 and, regardless of his age, the general time frame for a return for pitchers who have had Tommy John surgery is 12 to 18 months, with many of them saying they didn’t fully feel like themselves again until two years after the procedure.
On paper, the rotation should be strong, composed of Cole, Max Fried, Carlos Rodon, Cam Schlittler and Luis Gil, with Will Warren as an option as well.
5. Will there be any major organizational changes stemming from the ALDS loss?
All indications are that general manager Brian Cashman (signed through next season) and manager Aaron Boone (signed through 2027) remain good in the eyes of owner Hal Steinbrenner. Look at it this way: After the embarrassment that was the playoff-less 2023, the organization all but doubled down on how it operates. The Yankees did put an emphasis on defense this year, unlike in the past, when it generally treated it as a back-burner issue. This was reflected in the trade deadline acquisitions of Jose Caballero, Ryan McMahon and Amed Rosario.
Maybe there’s a change or two on Boone’s staff, but the Yankees, for better or worse, collectively have never been more sure of their overall methodology. If “The Process” World Series was a thing, the Yankees might be 10-time defending champions.
Erik Boland started in Newsday's sports department in 2002. He covered high school and college sports, then shifted to the Jets beat. He has covered the Yankees since 2009.
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