Juan Soto's decision to head across town got the New York Yankees' offseason off to a rough start last year. GM Brian Cashman and his staff did a nice job of recovering after the loss of the left-handed slugger, but they'd prefer not to lose another crucial internal free agent this year.
The Yankees have nine eligible free agents heading into the offseason but keeping all of them in the fold is not in Cashman's plans. A handful of the veterans won't be back for another season in pinstripes because they did not do enough to help the team in 2025.
That does not mean New York can afford to let the entire class walk and replace them on the open market. Keeping hold of these three veterans is a crucial part of Cashman's offseason plans. If any of these stars bolt the Bronx in the coming weeks, it will deal a serious blow to the franchise's World Series aspirations in 2026.
Cody Bellinger is the top priority for the Yankees
Cody Bellinger is comfortably the biggest free agent the Yankees have a chance to retain. He arrived in New York with relatively modest expectations last year but he ended up slugging 29 home runs and posting a healthy WAR of 5.1 in his lone season with the club.
Aaron Judge is the only outfielder certain to retain a spot in manager Aaron Boone's starting lineup next season. Trent Grisham is also headed to free agency, but New York did take a meaningful step towards retaining him by making him a Qualifying Offer. Jasson Dominguez and Spencer Jones both have a chance to carve out meaningful playing time, but they could easily start the campaign as fourth outfielders.
The one caveat here is that Cashman could opt to spend big on Kyle Tucker instead of bringing Bellinger back via a long-year deal. Any offseason that doesn't see Tucker or Bellinger holding up a Yankees' jersey at a high-profile press conference will be seen as a disaster for Cashman and his staff. He's likely going to be overpaid on the open market but the Yankees can't afford to cheap out and let Bellinger play elsewhere.
Trent Grisham made more than enough of a case to stay in NY
The aforementioned Grisham is another player the Yankees need to bring back for at least one more season. He's a prime candidate for offensive regression after a career season in 2025, but the lack of viable options available on the center field market make him a prime candidate to return to the Bronx.
The big question is whether or not Grisham will accept the team's Qualifying Offer. That would represent an overpay by the Yankees, but it would limit the team's exposure to just a one-year deal. If Grisham and his representatives are smart, they'll try to squeeze a three-year deal out of the Yankees with a slightly lower average annual value.
The only way the Yankees can afford not to bring Grisham back is if they find a better option in center field via a surprising trade. That option can't be ruled out but bringing the veteran lefty seems like a much more straightforward option for New York's front office.
Luke Weaver is the bullpen piece Cashman can't let walk
Luke Weaver is not hitting free agency at the best time. He struggled with pitch-tipping down the stretch last year and those ugly outings will suppress his free agent price tag. The Yankees would be wise to take advantage of that and ink him to a new contract to keep him in Boone's bullpen.
Weaver is at his best when he's permitted to operate as a flexible late-inning option. He's performed well as the team's closer at various times, but New York should be looking for a new, bulletproof option to handle things in the ninth. Weaver can give Boone more value as a versatile, multi-inning option who can operate in various high-leverage situations.
The Yankees need to make sure they don't overcommit to Weaver with a long-term deal, but giving him two or three-years of guaranteed money as an above-average reliever could turn into a terrific value. The Yankees should move quickly to retain his services before a competitor beats them to the punch.