The New York Yankees are heading into one of their most important offseasons in recent memory. After another disappointing playoff run, the team faces a long list of free agents and several crucial decisions that could reshape the roster for 2026 and beyond.
General manager Brian Cashman has plenty to weigh, starting with three names that played major roles in 2025 — Cody Bellinger, Trent Grisham, and Devin Williams. Each presents a different kind of decision: one feels like a must-keep, one screams risk, and one could hinge on trust.
Bellinger’s consistency makes him a clear priority
Let’s start with the obvious. The Yankees love Cody Bellinger, and it’s not hard to see why. He’s versatile, reliable, and one of the few players who stayed on the field all year — 152 games, his most since 2019.
Bellinger hit .272 with 29 home runs and 98 RBIs, posting a balanced offensive season that complemented his elite defense. His ability to move between center field and first base gives the Yankees rare flexibility, and that kind of value is hard to replace.
Yes, his postseason performance dipped after suffering a heel injury, but it’s hard to hold that against him. In a year where durability was a problem across the roster, Bellinger was the steadying force. Expect Cashman to prioritize re-signing him, even if it takes a long-term deal.
Grisham’s breakout comes with too much risk
Trent Grisham, on the other hand, feels like the kind of player the Yankees will thank and quietly move on from. The 29-year-old had an excellent 2025 season offensively — hitting .235 with 34 homers, 74 RBIs, and a 129 wRC+ — but that production came out of nowhere.
Before this year, Grisham hadn’t been an above-average hitter since 2021, and his defensive regression raises red flags. Once a Gold Glove-level outfielder, he slipped into negative territory this past season, costing the Yankees runs instead of saving them.
Cashman knows better than to pay for a fluke. Grisham will likely chase a multi-year deal from a rebuilding team willing to gamble on his 2025 numbers, but that gamble won’t come from the Bronx.
Williams could get one more shot in pinstripes
The decision on Devin Williams will be a little trickier. The 30-year-old closer had a rough regular season, posting a 4.79 ERA over 56.1 innings, but he rediscovered his form in October, flashing the nasty stuff that once made him one of baseball’s most unhittable relievers.
It’s possible the Yankees extend a qualifying offer worth around $21 million for one year. Williams has the stuff to bounce back — his strikeout rate remains elite, and his playoff flashes were a reminder of what he can be when his mechanics are locked in.
If the Yankees walk away now, and Williams rebounds elsewhere, it’ll sting. Cashman knows it. A one-year prove-it deal might make the most sense for both sides.
Depth pieces and veterans on the way out
Beyond those headliners, several role players are also hitting free agency. Amed Rosario, Austin Slater, Luke Weaver, and Ryan Yarbrough are all expected to test the market. Yarbrough could still return — his ability to eat innings and spot start is valuable, even if his fastball barely touches 90 mph.
Weaver could also be a cheap retention due to his volatility this past season.
The Yankees hold a 2026 club option on lefty Tim Hill, who quietly posted a 3.09 ERA over 67 innings. That should be a no-brainer to pick up. As for Paul Blackburn and Paul Goldschmidt, the writing’s on the wall. Blackburn will likely depart, while Goldschmidt, 38, could be nearing retirement after a one-year stint as a veteran mentor and specialist against lefties.
The Yankees’ offseason priorities are clear: retain the right pieces, get younger, and rebuild a bullpen that ran out of gas. But the choices they make in the coming weeks will set the tone for how serious they are about finally getting back to championship form.