5 moves Yankees must make to salvage no-show at 2025 Winter Meetings

Brian Cashman missed November's general manager meetings, and while he was in attendance in Orlando for the Winter Meetings, typically the part of the year where hot stove season reaches a fever pitch, the New York Yankees executive might as well have sat this one out as well.

The Yankees have come away without any major signings or trades. They nabbed Cade Winquest, a minor league hurler from the St. Louis Cardinals, in the Rule 5 Draft. The only rumor of substance they've been involved in is the strange interest in Colorado Rockies outfielder Brenton Doyle, because what team doesn't need a replacement-level outfielder?

Fortunately, the Winter Meetings as a whole were a relatively quiet affair, giving Cashman and the Yankees the opportunity to arise from their slumbers and actually improve the team, proving that the handwringing about profits and insistence that there isn't a strict budget can co-exist in a way that proves they can actually improve the team for 2026.

5 moves the Yankees can make to prove that a quiet Winter Meetings won't torpedo their 2026 chances

Sign Kyle Tucker to a short-term, high AAV deal with opt-outs

One of the undercurrents of this winter's proceedings is how the looming labor uncertainty will impact this free-agent crop. A lockout in 2027 is possible, and the rules could change drastically with a potential salary cap being on the table.

Kyle Tucker was long rumored to secure a massive $400 million deal that would span close to a decade, but coming off a good-but-not-great year, combined with the upcoming CBA drama, has led some to believe that a short-term deal to reset his market might be the way things play out.

In that case, the Yankees should be all-in. A three or four-year deal with a couple of opt-outs and a high AAV could do the trick, and would give the club another bright star who can do everything Cody Bellinger did well, and more.

Sign Japanese star Kazuma Okamoto

Brian Cashman has emphasized the need to add right-handed balance to the lineup and lean into more platoon options, and Japanese star Kazuma Okamoto could be a super platoon option for the club.

Okamoto has experience at both infield corners, as well as left field, all of which are positions where a right-handed complement is needed. A proven power threat, Okamoto's performance against higher velocities gives him a better chance to translate than most who come over from Japan.

Additionally, he comes with a diverse and varied skill set that features an above average walk rate, a better than average strikeout rate, and contact prowess that works hand in hand with his power potential. By rotating through first base, third base, and left field, as well as the occasional DH day, he'd be able to log a full season's worth of plate appearances while keeping the rest of the lineup fresh.

Sign Michael King to a three-year deal

The Yankees need to add another starter, but how they do that is tricky. The top remaining free agents, Framber Valdez and Ranger Suarez, both have red flags, but as southpaws they would be overkill on the Yankees' staff.

Tatsuya Imai brings tantalizing potential, but he is a high-variance gamble that will require a lot in dollars and years. With the injury issues and uncertainty regarding the likes of Gerrit Cole, Luis Gil, and Carlos Rodón, bringing in an option with as much stability as possible is paramount.

That's where Michael King comes in. The former Yankee has proven he can pitch in New York, and while his injury woes in 2025 are a concern, his well-above-average performance can alleviate that. All starters come with risk, and in this case, the devil you know is better than the devil you don't.

Swing a trade for San Diego Padres reliever Jeremiah Estrada

Fixing the bullpen cannot be overlooked. As volatile as Devin Williams and Luke Weaver were, the Yankees have done nothing to replace them. A dominant strikeout arm to set up for David Bednar would give the bullpen a different feel, and stealing one away from the league's best bullpen in 2025, the San Diego Padres, would be the best way to go about it.

The Yankees and Padres have done business before, and AJ Preller is always looking to make a big trade. One of the most likely names to be moved is that of Jeremiah Estrada, and the Yankees should be salivating at that possibility.

Estrada posted an absolutely dominant 35.5% K-rate in 2025, and that's no fluke, with the 27-year-old right-hander being even more lethal in 2024 with a 37.3% clip. He's also under team control through 2029, making him a valuable piece for the future.

San Diego is said to be seeking major league-caliber players and has a need for starting pitching. Will Warren could fit that bill, and if King is brought in for the rotation, he might be an expendable piece.

Double down on the bullpen by signing Tyler Rogers

The knuckle-dragging submariner might be an oddity, but in a sea of volatility, Tyler Rogers has been the paragon of consistency. The soon-to-be-35-year-old has pitched 70 innings or more every season from 2021 onward. Over that same time period, he owns a 2.71 ERA.

The Yankees can't simply count on Camilo Doval to bounce back, nor can they truly believe that Jake Bird can become something. Instead, they must secure one of the majors' most reliable bullpen presences, even if he is extremely unorthodox in how he gets outs.