Examining Yankees free agency targets as MLB Winter Meetings arrive

Examining Yankees free agency targets as MLB Winter Meetings arriveStory byThe Bergen RecordPete Caldera, NorthJersey.comThu, December 4, 2025 at 9:01 AM UTC·4 min read

NEW YORK - Trent Grisham accepted the $22.025 million free agent qualifying offer last month, having a dual effect on the Yankees’ winter strategy.

At least they had some insurance in center field, a thin position in MLB’s marketplace.

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But it’s already a hefty 2026 contract for a club that – ideally, per owner Hal Steinbrenner – would like to lower its $319 million payroll of 2025.

That “ideal’’ plan could also “go bye-bye in two seconds,’’ Steinbrenner said recently, based on player recommendations presented by GM Brian Cashman.

“The job right now is to find out what’s available,’’ Cashman said in the leadup to MLB’s Winter Meetings. “And those all have different price points.’’

Let's examine where the Yankees - who routinely inquire on nearly all impact free agents - might go in this winter's market.

Yankees' free agent priority: Cody Bellinger

Mar 20, 2025; Sarasota, Florida, USA; New York Yankees outfielder Cody Bellinger (35), New York Yankees third base Jazz Chisholm Jr. (13) and New York Yankees outfielder Aaron Judge (99) high five after scoring during the third inning against the Baltimore Orioles at Ed Smith Stadium. Mandatory Credit: Kim Klement Neitzel-Imagn Images

Asked about Bellinger last month, Cashman said “we’d be better served if we can retain him. If not, we’ll have to look at alternative ways to fill it and see where it takes us.’’

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If the deep-pocketed Dodgers, Phillies and Mets are in pursuit, would it be surprising to see Bellinger commanding $30 million annually for at least five years?

After Kyle Tucker, the 30-year-old Bellinger is the best outfield option in free agency, and Tucker’s final price might land above $400 million.

And if Tucker signs first, agent Scott Boras likely gains further negotiating leverage by representing the clear-cut best outfield option remaining in free agency - one with a track record of success in L.A., Chicago and New York.

Yankees potential free agent position targets

Mar 21, 2023; Miami, Florida, USA; Japan first baseman Kazuma Okamoto (25) bats against the USA in the sixth inning at LoanDepot Park. Mandatory Credit: Rhona Wise-USA TODAY Sports

Asked about the potential to sign a Japanese free agent, Cashman said he’d “play in those markets if it’s a fit for us.’’

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Based on scouting reports, right-handed hitting corner infielder Kazuma Okamoto’s power, plate discipline and plus defense could provide a solid complement to lefty hitters Ben Rice and Ryan McMahon.

By shifting between first and third (if that’s even appealing), Okamoto could get regular at-bats, especially if Rice remains a catching option.

After his bounce back season in Seattle, switch-hitter Jorge Polanco could be a consideration for his versatility and .896 OPS versus lefty pitching in 2025.

A one-year reunion with infielder Amed Rosario can’t be ruled out, with the added benefit of his leadership and New York experience.

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Speaking of reunions, Cashman has checked in with first baseman Paul Goldschmidt's rep (.981 OPS vs. lefties in '25). Old friend Miguel Andujar has been lethal against lefty pitching, though his defense at third base and left field remains subpar.

And on the high-end side, if the Yanks fail to reel in Bellinger, would they use those savings to pursue first baseman Pete Alonso?

In need of a right-handed hitting backup catcher, AL East veteran Danny Jansen might be a pricey one-year option suited to more regular play, but he's a solid choice worth exploring.

Yankees potential free agent pitching targets

San Francisco Giants pitcher Justin Verlander (35) reacts after putting two Arizona Diamondbacks runners on first and second bases in the fourth inning at Chase Field in Phoenix on Sept. 17, 2025.

There’s an acute need to improve the Yankees’ setup relief, but they’re likelier to find relievers via trade – as they did with Devin Williams and Fernando Cruz last winter.

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Bidding on big, free agent bullpen arms – led this time by Edwin Diaz – hasn’t been a Yankee trait in recent years, and they’re also likely to see Luke Weaver follow Williams (Mets) to another club.

Steinbrenner’s stated satisfaction with his rotation doesn’t rhyme with a pursuit of big-name starters, a group that includes Japan’s Tatsuya Imai.

Last year, Max Fried ($218 million) made it a trio of expensive, pinstriped free agent starters, joining Gerrit Cole ($324 million) and Carlos Rodon ($162 million).

But Cole, Rodon and Clarke Schmidt will start the season on the injured list, and there’s incentive to add a one-year veteran option – perhaps inviting Justin Verlander and Max Scherzer into the conversation.

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Right-handers Chris Bassitt, Merrill Kelly and Nick Martinez are potential short-term options, while Michael King - reluctantly traded in the Juan Soto deal - is a far more expensive but worthy target.

This article originally appeared on NorthJersey.com: Yankees free agency targets as MLB Winter Meetings arrive

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