The New York Yankees’ season did not end in the way they would’ve liked it to. After Wednesday’s 5-2 loss to the Toronto Blue Jays, the organization has a lot of decisions it needs to ponder this offseason. In particular, they have to worry about multiple key players hitting free agency.
What The Yankees Are Facing in Free Agency
To start, two of New York’s three starting outfielders will almost certainly hit the open market. There’s Trent Grisham, who had a career year with 34 home runs, 74 RBI, and an .812 OPS; and there’s Cody Bellinger, who revived his status as a star-caliber player by posting an impressive 5.0 brWAR. The latter, however, has a player option for 2026 worth $25 million, which, with Scott Boras as his agent, he will almost certainly exercise.
Then there’s the even more unlikely returns: Devin Williams, Luke Weaver, and Paul Goldschmidt could very well have ended their tenures in the Bronx, despite all of them stating their desires to come back to New York. So, who are the Yankees likely to retain for 2026, and who are they going to let walk?
The Likely Returns
Let’s start with who the Yankees would probably like to keep on the roster for next season. Williams, acquired from Milwaukee last offseason, was more or less a disappointment in 2025, with small spurts of success scattered among the disasters. Though his 4.79 ERA definitely decreased his value as a free agent, this could work out in the Yankees’ favor; Williams was a key piece of the bullpen down the stretch in September and into the postseason. The Yankees would have never signed him at top-dollar, so if the price is right, New York should definitely keep the two-time National League Closer of the Year.
In terms of the outfield, one would assume that the Yankees must keep either Bellinger or Grisham. With Jasson Dominguez looming in the wings for a starting spot, there is still one more spot in the outfield that must be filled, ideally with a solid defender. Both will likely earn a big payday, either in New York or elsewhere, so it might simply be a matter of who is willing to take less money to stay.
The Less-Likely Returns
Unfortunately, the Yankees are almost definitely saying goodbye to veteran Paul Goldschmidt. The longtime Arizona Diamondbacks and St. Louis Cardinals’ first baseman had a solid one-year tenure in New York, despite losing playing time as the year went on to Ben Rice. The latter has emerged as New York’s first baseman/backup catcher of the future, so they have no reason to retain Goldschmidt.
Then there’s the case of Luke Weaver. He was one of, if not the, best reliever out of New York’s bullpen in 2024 and for the first half of this season. After that, he just completely fell apart, posting a 4.40 ERA in the second half. It will be an interesting decision to see whether or not the Yankees bring him back, to say the least.
Also hitting free agency are left-handed reliever Ryan Yarbrough, right-handed relievers Jonathan Loáisiga and Paul Blackburn, and trade-deadline utility pickup Amed Rosario. The Yankees do not typically bring back relief pitchers unless they can nab them at great value (see the Tim Hill situation last offseason), so they will probably look to their internal system to find more pitching talent. Bringing back Yarbrough in particular would not be a bad idea, though; the 33-year-old started eight games for the Yankees towards the middle of the season, putting up a 3.83 ERA over 40 innings.
Many, Many Questions
The bottom line is that this upcoming offseason for the Yankees is already full of questions and decisions that will not be easy to resolve. Their 2025 roster was arguably one of the best they’ve had in the Judge era, and with the team’s captain turning 34 next season, how many more shots will he have to deliver a World Series to the Bronx finally?
Main Photo Credits: Kevin Sousa-Imagn Images
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