Every Yankees Player Set to Become a Free Agent This Offseason

An offseason that will require some self-inflection begins with decisions on several free agents.

Jazz Chisholm Jr. (left) and Trent Grisham (right) are two of several unrestricted free agents for the New York Yankees. | IMAGN IMAGES via Reuters Connect

The New York Yankees' season has come to a startlingly sudden end with a sweep at the hands of the Tampa Bay Rays, concluding in Game 3 of the ALDS on Wednesday night in the Bronx.

While there will be plenty of discussion on the long season we just witnessed, you don't make progress by looking backwards. Starting today, the front office and Brian Cashman will have to figure out how to navigate a likely lockout that will doom the offseason and how to ensure that, by the time we do eventually get baseball again, there's a roster more likely to jump what's becoming an in-division hurdle.

The first move that any team makes in an offseason is deciding who should stay and who should go. After all, a designated period of exclusive negotiating will happen immediately after the World Series.

Here's a list of every Yankee, sorted by 2026 salary, hitting the market this offseason.

Trent Grisham - UFA

Sometimes, you just overstay your welcome.

If Trent Grisham signed elsewhere last offseason, he would be considered a very good Yankee looking back as someone who turned from a throw-in salary dump in the Juan Soto trade to a leadoff hitter and center fielder for a very good offense in 2025.

His performance earned him a qualifying offer, which he accepted, looking to have another good season and parlay that into a big, multi-year deal. After this disaster of a season, it's safe to say his future outlook is significantly bleaker.

The decision to extend the qualifying offer was not a mistake on the Yankees' part. As much as some may believe this hard regression was expected, teams don't make decisions based on what players did five years ago.

In 2026, Grisham still had stretches of great baseball, but ultimately regressed to a .211/.308/.395 slash line with a 98 wRC+ and just 0.7 fWAR. With his glove collapsing as it did due to numerous hamstring injuries crushing his athleticism, the bat couldn't be this rough.

Whether they have data to suggest they can get 2025 Grisham back or not, he isn't a fit for this team anymore, nor is he a fit anywhere in center field. His future is in a corner outfield spot elsewhere that'll be less physically taxing.

Jazz Chisholm Jr. - UFA

No player has been more polarizing among baseball fans in pinstripes than Chisholm has been of late. He has by far the most personality of any Yankee in a long time, and for a while, the city embraced the Bahamian flair.

But like Grisham, a good tenure is now going to end with a black mark. After boldly calling his shot at a 50/50 season in spring training, he seemed to crumble under the pressure of lofty expectations in a contract year, sinking to a .231/.312/.399 slash line with a 98 wRC+. Every time he seemed to get going, he'd look lost again or suffer an injury halting his momentum.

As for his offseason outlook, there's a chance the Yankees extend the qualifying offer to a guy whose floor is high enough with his defense and baserunning that he still accrued 3.5 fWAR in an ugly season, but it would be best for both parties to split.

David Bednar - UFA

The New York Yankees should try to bring back reliever David Bednar (right) this offseason. | IMAGN IMAGES via Reuters Connect

It's hard to find a consistently good closer. It's equally hard to find someone who makes the jump from a small market to the shining lights of the Bronx and doesn't wince.

David Bednar has been with the Yankees since being acquired at the trade deadline in 2025. He slowly earned his way to being the closer by October of that year. He finished his first year and a half in pinstripes with a 2.39 ERA in 86 appearances, 111 strikeouts in 94 innings, and locking down 45 saves in 52 opportunities. He's also been a rock in October, allowing just one run in nine innings.

This is the type of player you re-sign, but the problem is that the Yankees have shifted away from paying relievers since the disastrous end of the "Super Bullpen" from 2020-22. He'll be one of the premier closers on the market with a big market entering his age-32 season. At a minimum, the Yankees should give him the $23 million qualifying offer, but should pursue a multi-year pact.

Paul Goldschmidt - UFA

New York Yankees first baseman Paul Goldschmidt is one of several players who will be free agents this winter. | IMAGN IMAGES via Reuters Connect

There's something poetic about a potential future Hall of Famer ending his career in pinstripes. It's even better when he's not a total husk of himself. We didn't get close to prime Paul Goldschmidt over the last two years, but he was a good Yankee.

Initially signing as a successor to Anthony Rizzo, Goldschmidt gave way to the emerging Ben Rice and gradually sank deeper into a role as a righty platoon bat. Re-signing late in the offseason, he served as insurance for an injured Giancarlo Stanton and did his job in that aspect. In his two years as a Yankee, he slashed .265/.322/.423 with a 105 OPS+ and 2.3 fWAR.

The 39-year-old absolutely still has gas left in the tank as a strict platoon bat, but you wonder if he'd be redundant on a team with multiple first basemen and a big Giancarlo Stanton question. In 2026, he slashed .299/.393/.573 with a 168 wRC+ against left-handed pitching.

John Schreiber - UFA

Now to the reliever section, starting with the only midseason acquisition (off waivers).

John Schreiber is very good at his niche. He's there to get right-handed hitters out, which he does better than almost anyone in baseball. The Yankees got him off waivers from the Kansas City Royals in August and gave him an audition, so it's anyone's guess what his future outlook is.

His market will likely be limited due to him being a righty specialist, so it's in play that the Yankees bring him back as they did with Paul Blackburn last year and try to tweak things to make him more of a leverage option.

Tim Hill - UFA

It's truly sad how many people who were huge parts of the team's success in 2024 and 2025, like Tim Hill, are ending their Yankees tenures on a sour note.

Since he was claimed off waivers in early 2024, the funky lefty has been one of the best lefty specialists in baseball. And for a time, he even got enough outs against righties, putting him high on the trust tree. Through 2025, he had a 2.6 ERA in 111 innings as a Yankee.

However, things fell apart in 2026. When you're a soft-tossing, arm-angle-reliant guy like Hill is, the slightest mechanical error can completely end your career.

The 36-year-old reliever became unplayable for stretches and yielded significantly more barrels and home runs than before due to poor location. As such, he was left off both playoff rosters and will not be a Yankee in 2027.

Ryan Yarbrough - UFA

The Yankees re-signed Ryan Yarbrough to provide rotation depth as a built-up long reliever in the bullpen. But the team's plethora of strong rotation options and few instances of needing extra arms left him in the same role in low-leverage situations.

He was a useful pitcher, however. When you give a guy $2.5 million, who gives you a 3.69 ERA across 68.2 innings, you take that every day of the week. He exists at the same volatile level as Hill, where the 34-year-old could suffer a mechanical issue that torpedoes his career at any time, but he's a guy who, if you can get back for the same price, is worth considering.

Amed Rosario - UFA

New York Yankees third baseman Amed Rosario likely won't be returning to the Bronx after his struggles in 2026. | IMAGN IMAGES via Reuters Connect

The Yankees re-signed Amed Rosario for his ability to hit left-handed pitching and platoon with Ryan McMahon without being hopelessly bad defensively. In 2026, his platoon splits completely flipped, and his at-bats got dramatically worse against lefties, while his defense sank to "worst in baseball" levels.

He was left off an ALDS roster that still had 15 position players, which shows the Yankees are just about done with him.

Paul Blackburn - UFA

In a perfect world, the New York Yankees would want to bring back pitcher Paul Blackburn, as he was one of their more reliable bullpen options. | IMAGN IMAGES via Reuters Connect

Maybe the biggest offseason question mark about an internal free agent is Paul Blackburn, whose breakout 2026 stabilized the bullpen but also puts him in line for a big payday.

Blackburn, a failed starter with the Athletics and New York Mets, signed with the Yankees in 2025 as a long reliever and saw enough to bring him back this season for just $2 million. Whatever changes they made worked in a big way, as he broke out with a 1.69 ERA in 85 innings. He became one of baseball's best relievers out of nowhere.

The Yankees should want the soon-to-be 33-year-old back. Blackburn should want to return to the place that revived his career. The problem will be if someone looks at the veteran's 2026 results and overpays for him in the offseason while searching for bullpen help. In a world where the team should try hard to retain Bednar, Blackburn's price will depend on whether he's a Yankee in 2027.

Get Yankees On SI straight to your inbox: sign up for our free newsletter here.