The New York Yankees face another winter of high pressure decisions after falling short of their championship expectations yet again.
Following a disappointing playoff exit, the organization is facing calls to move on from manager Aaron Boone. But however the front office resolves the future of the team’s manager, it will also have to make some difficult free agent decisions for some key roster members.
“It’s been a week since the New York Yankees’ season ended, the final humiliation a three-game sweep in the American League Division Series by the Tampa Bay Rays. Since then, there’s been radio silence from the club as it licks its wounds and figures out what’s next,” Brendan Kuty wrote for The Athletic. “But the team also has a slew of pressing roster questions.”
A pair of those questions involve some key members of the roster who will reach free agency, with the Yankees needing to decide whether or not to extend a qualifying offer in an initial attempt to retain them.
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Two of those questions concern players who could depart in free agency, and who appear to have very different evaluations from the front office.
According to the New York Post’s Yankees insider Jon Heyman, the club is expected to take vastly different approaches on star closer David Bednar and polarizing infielder Jazz Chilsholm Jr.
“The Yankees are expected to extend the $23.15M qualifying offer to free-agent closer David Bednar, who had a terrific year, sources say,” Heyman reported. “Meantime, it’s believed the Yankees are unlikely to extend the same offer to second baseman Jazz Chisholm Jr., which would represent a shocking turn off his 30-30 2025 season.”
The reported plan would put Bednar in position to most likely decline the one-year offer and pursue a longer-term agreement, which could still be furnished by the Yankees. Extending the offer would provide a chance to retain a productive late-inning reliever while potentially securing draft-pick compensation if he declines and signs with another team.
Chisholm’s situation appears less straightforward. Despite his impressive 2025 campaign, the second baseman’s uneven performance this season may have complicated the club’s assessment of his future.
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Chisholm has expressed interest in returning to New York, but that does not necessarily mean the Yankees share his preference.
“Chisholm kindly said he’d like to be back after the Yankees’ sudden playoff exit, but word is Yankees higher-ups believe it’s time to move on following his rough season,” Heyman reported. “(They may also believe he might accept considering he said he wants to stay.)”
The qualifying offer is not the only way for New York to retain either player, and the reported expectations do not constitute official decisions. Still, the contrast suggests the Yankees could prioritize keeping Bednar while exploring alternatives at second base.
After another postseason disappointment, those choices will help determine whether New York makes meaningful changes or largely runs back the same group in 2027.
This article was originally published on Forbes.com