Once again, the New York Yankees enter the offseason following a disappointing playoff exit, as they lost to the Tampa Bay Rays in the ALDS.
While the team didn’t have Aaron Judge at its disposal in the playoffs, there was still the expectation that New York could make a deep playoff run. Instead, the Yankees head back to the drawing board to try and figure out how to best build around their star players.
Aaron Judge will, of course, be back, hoping for a healthier season after he had an injury-riddled 2026 season. Judge is getting older, though, and his superstar abilities will only be on display for so much longer before New York has to reckon with a diminished version.
This offseason could be strange, with the lockout looming, but the Yankees are in good shape regarding most of their team for 2027. However, fans will demand major changes with another year going by without a World Series title, even if the market for players isn’t as robust as in years past.
Here’s a breakdown of how the Yankees can approach this crucial offseason.
Yankees free agents 2027
- OF Trent Grisham
- 2B Jazz Chisholm Jr.
- RP David Bednar
- RP Paul Blackburn
- 1B Paul Goldschmidt
- IF Amed Rosario
The Yankees have most of their roster set to return in 2027, with only a few notable free agents hitting the market. Trent Grisham and Jazz Chisholm Jr. are the biggest names, but New York has possible in-house replacements for them in Spencer Jones and Anthony Volpe making it so the team can move forward without them.
The area that will need total attention for the Yankees in the offseason is the bullpen. David Bednar was excellent for the team since the 2025 trade deadline, making it so he should be New York’s top free agency priority. Paul Blackburn also hits free agency after a career year along with other Yankees middle relievers, and New York will have either bring them back or replace them next year.
Of note, the Yankees are set to bring back their entire rotation, which was one of the best in baseball in 2026. The six-man group led by Cam Schlittler is as deep as any team’s rotation, with the lone free agent being Clarke Schmidt coming off of Tommy John surgery.
MORE: Yankees playoff history with Aaron Judge
Yankees offseason targets
Entering the offseason, the biggest area of offensive improvement the Yankees could make is in the infield with Jazz Chisholm hitting free agency and Ryan McMahon on the final year of his deal. New York should have Ben Rice, Luis Garcia Jr. and George Lombard Jr. all play big roles, but they could use some help.
The free agent market, however, is thin this year, especially on the infield. The best infield free agent would be Bo Bichette if he opts out of his deal, but he is more likely to return to the New York Mets for another season. Other possible targets include Brandon Lowe, Gleyber Torres, Luis Arraez, Alec Bohm and J.P. Crawford.
If the Yankees look towards the trade market, there are a few options that could come into play. The Washington Nationals could look to move C.J. Abrams, and New York could inquire about Los Angeles Angels shortstop Zach Neto or Houston Astros shortstop Jeremy Pena.
For the bullpen, Bednar is perhaps the best closer on the market, so it would be prudent for New York to re-sign him. Otherwise, the Yankees could look to veteran relievers like Raisel Iglesias, Jason Adam or Evan Phillips on the free agent market, or they could try to trade for a closer like Jhoan Duran of the Philadelphia Phillies.
It’s also possible the Yankees pursue Tarik Skubal in free agency, like the rest of the big-market teams, but New York’s full rotation means that isn’t a need.
MORE: Should the Yankees fire Aaron Boone
Will Yankees fire Aaron Boone?
For the Yankees to make a big move, they could look to shaking up the coaching staff. Aaron Boone has been the team’s manager for the last nine years, making the playoffs eight times but failing to secure the coveted World Series championship.
At some point, the Yankees will decide to go in a different direction at manager, but the possible managerial targets aren’t too clear. Joe Espada, the Astros manager since 2024, was a former Yankees coach and could be out of a job in Houston, while Yankees legend Don Mattingly has plenty of managerial experience himself. The Yankees could also try to lure Rob Thomson back to New York, as the former Phillies manager spent a few decades with the Yankees organization.
