The Yankees are heading into another winter with a long list of familiar names at the center of the conversation.
When the 2026 World Series wrapped up with the Milwaukee Brewers celebrating the first championship in franchise history, New York was left to sort through its own unfinished business. According to the MLB Players Association, 144 players have been declared free agents, and 10 of them came from the Yankees.
That group includes Jazz Chisholm Jr., Trent Grisham, David Bednar, Paul Goldschmidt, Paul Blackburn, John Schreiber, Ryan Yarbrough, Tim Hill, Amed Rosario, and Michael Fulmer.
This isn’t just a pile of fringe pieces, either. The Yankees are staring at decisions involving their starting second baseman, center fielder, closer, and multiple bullpen arms. For a club coming off another disappointing October exit, the fallout could help shape what the 2027 roster looks like.
Jazz Chisholm Jr. is one of the biggest wild cards. He hit .231 with 19 home runs, 55 RBIs, and 41 stolen bases over 137 games, giving the Yankees flashes of the dynamic athlete they wanted - speed, defense, and enough pop to change a game.
But the offensive dip was real, and his postseason finish didn’t help his standing. Being benched during the ALDS made for a rough ending.
There’s also a strong chance the Yankees let him walk. Reports suggest they’re unlikely to give him the approximately $23.15 million qualifying offer, and with Anthony Volpe potentially moving to second base down the line, the path forward may not include Chisholm.
Trent Grisham appears to be in a similar spot. He accepted the qualifying offer after his strong 2025 campaign, but 2026 was a different story.
He finished at .211 with 18 home runs and a .703 OPS, and his defensive numbers slipped as well. That’s a tough profile for an everyday center fielder, especially with Spencer Jones and Jasson Domínguez available as internal alternatives.
The feeling here is that the Yankees have seen enough.
David Bednar, though, is a different conversation entirely. He posted a 2.47 ERA and saved 35 games, showing he could handle the pressure that comes with closing in New York.
That kind of reliability matters, and the Yankees would be wise not to let it slip away. He could get a qualifying offer, but a multiyear deal may be what keeps him in the Bronx.
Retaining Bednar should be near the top of the priority list.
Paul Goldschmidt remains in the mix as a veteran first baseman who can still hit left-handed pitching, but age changes the equation. At 39, the Yankees have to be cautious about how much they commit to him, especially with Ben Rice becoming an important offensive piece.
The bullpen depth arms are a more straightforward call. Paul Blackburn and Ryan Yarbrough could come back on short-term, affordable deals. Tim Hill, John Schreiber, Michael Fulmer, and Amed Rosario don’t look irreplaceable, even if they add some depth.
The bigger issue is what comes next. The Yankees already have major money tied up in Aaron Judge, Gerrit Cole, Max Fried, Carlos Rodón, and Cody Bellinger. Add in a weak free-agent market and the possibility of another MLB labor dispute, and the front office may need to get more aggressive in trades rather than waiting for the market to solve its problems.
Brian Cashman and Aaron Boone are back for a reason, and it wasn’t to run out a version of the same roster with a few different bench names attached. Ten Yankees hitting free agency opens the door to real change.
Now the question is whether the organization is ready to make it.
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