The New York Yankees are heading into one of their most pivotal offseasons in recent memory — one that could redefine their roster and competitive window. Seven players are set to hit free agency, clearing roughly $60.35 million from the payroll and giving general manager Brian Cashman a rare blend of financial flexibility and roster uncertainty.
It’s a fresh start on paper. In reality, it’s a puzzle that needs to be solved quickly.
Bellinger headlines the offseason decisions
Cody Bellinger is the most expensive and most interesting name among the departing players. His $27.5 million salary in 2025 — partially covered by the Cubs in last summer’s trade — will come off the books, but the Yankees face a tough call on whether to bring him back.
Bellinger is expected to decline his $25 million player option for 2026, chasing a long-term payday after a resurgent year. He hit .272/.334/.480 with 29 home runs, 98 RBIs, and a 125 wRC+. Just as importantly, he played elite defense across multiple outfield spots while staying healthy, something the Yankees desperately needed.
Paying him won’t come cheap, but it might make more sense than doubling that number for someone like Kyle Tucker. Bellinger’s fit — both in Yankee Stadium’s dimensions and in the clubhouse — makes him a strong candidate for an extension if the price doesn’t spiral out of control.
Devin Williams’ late surge raises questions
Another key decision involves closer Devin Williams, who had a volatile regular season but rediscovered his form when it mattered most. After a rocky start, Williams locked in down the stretch and became nearly unhittable during the playoffs, giving the Yankees a glimpse of what their bullpen could look like at full strength.
He’s hinted that he enjoyed his time in New York, which could open the door for a reunion if both sides agree on a short-term deal coming off a volatile season. For a team that’s seen too many blown leads in October, keeping a proven closer like Williams could stabilize the backend of the bullpen.
Veteran departures and young replacements
The rest of the group looks easier to move on from. Veterans Paul Goldschmidt, Trent Grisham, Luke Weaver, and Amed Rosario are all expected to test the market. Each played a role down the stretch, but none are locks to return given the team’s shifting priorities.
The Yankees appear ready to hand the left field job to Jasson Dominguez, who flashed star potential before his injury in 2024. Grisham’s departure opens the door for Dominguez to take on everyday duties alongside Aaron Judge and whoever fills the remaining outfield slot.
Cashman’s bullpen cushion and financial outlook
One thing Cashman doesn’t have to stress over this winter is bullpen depth. The trade deadline acquisitions of David Bednar, Camilo Doval, and Jake Bird fortified the unit. Still, pitching depth can unravel quickly, so expect the Yankees to bring in at least two veteran arms as insurance.
With roughly $70 million to spend before hitting the $300 million luxury tax threshold, the Yankees have room to maneuver — but not to waste. Every dollar will count toward balancing a roster that’s still searching for the right mix of youth, power, and durability.
The decisions they make over the next few months will dictate whether this offseason is remembered as a step forward or another patchwork job in a cycle that’s become too familiar in the Bronx.