The New York Yankees’ season ended with that familiar sting of unfinished business. They powered past the Boston Red Sox in the Wild Card Series but couldn’t overcome the Toronto Blue Jays in the Division Series, falling just short of another deep playoff run. Now, as the World Series wraps up and the offseason door creaks open, the Yankees are already preparing their next move.
Their winter checklist is long and layered: several players are headed for free agency, opening both roster spots and financial breathing room. But with that flexibility comes responsibility — and a string of decisions that could reshape the club’s direction heading into 2026.
Five Yankees land on top-50 free agent list
According to Jim Bowden of The Athletic, five players from the 2025 Yankees are among his top 50 free agents this offseason — a sign of both the roster’s depth and its volatility.
At No. 10 sits Cody Bellinger, the versatile outfielder and first baseman who rediscovered his rhythm in pinstripes. Bellinger hit .272 with 29 home runs and a .480 slugging percentage, reestablishing himself as one of baseball’s most dynamic power bats. Bowden expects him to opt out of his current deal and test the market again, betting on himself for a longer-term contract. The Yankees will have a tough choice: pay to keep his resurgence in the Bronx, or risk losing another middle-of-the-order threat.
Trent Grisham comes in at No. 24 after the best season of his career. The 28-year-old finally broke through offensively, blasting 34 home runs and becoming a steady presence in center field. Bowden projects a two-year, $30 million deal for Grisham, naming the Yankees among several logical fits. His blend of power and defense could make him a valuable piece, whether in New York or elsewhere.
Bullpen arms headline mid-tier rankings
Every contender needs reliable relief, and the Yankees’ bullpen could see notable turnover. Bowden ranks Devin Williams at No. 35 and Luke Weaver right behind him at No. 36.
Williams, known for his devastating “Airbender” changeup, remains one of baseball’s most electric late-inning arms when healthy despite an uneven season.
Bowden suggests a one-year, $10 million “prove-it” deal — a fair gamble for a pitcher who can change a game’s rhythm in a single pitch. Weaver, meanwhile, could command a two-year, $20 million contract.
A veteran first baseman near the end
Rounding out the group at No. 49 is Paul Goldschmidt, the veteran slugger whose reputation precedes him. The 38-year-old showed flashes of his old self in the first half of 2025, bringing leadership and professionalism to a lineup that often leaned young.
But his production faded as the season wore on. Bowden notes that Goldschmidt might be best suited for a part-time or platoon role moving forward. Given the Yankees’ push for youth and speed, his return feels unlikely.
What’s next for New York
The Yankees’ presence on Bowden’s list underscores the franchise’s crossroads. Five key contributors, five decisions that will test how far New York is willing to go to stay in contention. The front office has money to spend, yes, but also lessons to learn from another October that ended too soon.
In many ways, this offseason feels like a chess match — one where every piece matters, and every move must anticipate the next two. For the Yankees, the board is set. Now comes the strategy.