The Yankees have 2 glaring holes as Winter Meetings begin

As the baseball world descends on Nashville for the Winter Meetings this Sunday night, the New York Yankees find themselves in a familiar position: holding a checkbook that is ready to burst but a roster that is alarmingly incomplete.

While Brian Cashman has already made a move by extending Trent Grisham on the qualifying offer, that decision feels more like applying a band-aid to a bullet wound than a genuine solution. The pressure is mounting on Hal Steinbrenner to authorize a splash that signals the Bronx Bombers are serious about 2026, rather than just hoping their injured stars magically heal on schedule.

The narrative that the Yankees are “close” is dangerous because it ignores the glaring holes that could sink the ship before it even leaves the harbor.

We are looking at a team that is actively negotiating against itself in the outfield market while simultaneously staring down a rotation crisis that nobody seems to want to acknowledge. If the Yankees walk away from these meetings without a definitive answer in left field and a stabilizer for the rotation, the “championship window” might just slam shut on their fingers.

Vacant Outfield Spot: The Bellinger vs. Tucker Dilemma

The Yankees currently have one outfield spot accounted for with the return of Trent Grisham, but relying on him to be an everyday staple is a gamble this lineup cannot afford to take.

The real debate centers on whether the front office will finally meet Cody Bellinger’s price or pivot to a Kyle Tucker trade scenario that has been rumored for months. Bellinger is coming off a solid resurgence in 2025, slashing .272/.334/.480 with 29 home runs, proving he can handle the bright lights, but his asking price remains a sticking point for a front office that loves to count every penny.

On the other side of the coin, Kyle Tucker offers a slightly different profile, having hit 22 homers with a .377 on-base percentage last season, though his acquisition would require spending $350+ million.

Knowing Hal Steinbrenner’s tendencies, the smarter money is on the cheaper option, which likely points back to Bellinger or perhaps even an internal promotion if negotiations stall. However, if they decide to go the internal route, there is a “left-handed Aaron Judge” waiting in the wings who could force his way into the conversation, though banking on a rookie to anchor the outfield is a massive risk.

One More Solid Starting Pitcher: Stability Is Non-Negotiable

The rotation picture is arguably more terrifying than the outfield vacancy, specifically because the team’s two aces are starting the year on the shelf.

With Gerrit Cole recovering from Tommy John surgery and Carlos Rodon expected to miss the first few weeks of the regular season, the Yankees are essentially flying blind into April. It is malpractice to enter a season relying on depth pieces to carry the load against the AL East, which is exactly why the Yankees should be focused on pitching this offseason.

This desperation explains the heavy smoke connecting the Yankees to Japanese ace Tatsuya Imai, whose 1.92 ERA in the NPB last season suggests he has the stuff to translate immediately to MLB.

Imai isn’t just a depth piece; he is a potential frontline starter who could stop the bleeding while Cole and Rodon recover, offering the kind of high-upside stability the current rotation lacks. Whether they land Imai or attempt a reunion with Michael King, adding a proven arm isn’t a luxury anymore; it is the only thing standing between the Yankees and a disastrous first month.

Looking Ahead: Cashman Must Choose Aggression Over Caution

The Winter Meetings are rarely a place for the timid, and the Yankees have spent too many recent offseasons trying to be the smartest team in the room rather than the most talented.

The path forward is clear: secure a legitimate bat to pair with Aaron Judge and buy an insurance policy for the rotation that doesn’t rely on “hope.” If Cashman leaves Orlando with nothing but minor league deals and platitudes about “internal improvements,” the fanbase will have every right to hit the panic button.

This is the moment where the 2026 season is defined, not on Opening Day, but in the negotiation rooms of the JW Marriott Orlando Bonnet Creek Resort & Spa — not a bad destination for the GMs.

The Yankees have the resources to fix both problems by Sunday night, but it requires a willingness to overpay for certainty in an uncertain market. Tatsuya Imai and Cody Bellinger are sitting right there for the taking; the only question is whether the Yankees are bold enough to grab them.