The New York Yankees reach the Winter Meetings with as much promise as pressure. They believe they can contend in 2026 — but the roster says the window could slam shut just as quickly. Trent Grisham returned on the qualifying offer, Cody Bellinger remains a priority target, and top prospects Jasson Dominguez and Spencer Jones are pushing for roles. At the same time, the rotation is bruised, and the bullpen is missing key pieces. Next week in Orlando has a chance to determine whether the Yankees are in the race — or chasing one.
Rebuild the bullpen into a late-inning strength again
With Devin Williams now gone and Luke Weaver a free agent, too many high-leverage outs from last year are no longer accounted for. The Yankees still have David Bednar, who can finish games, but the path to the ninth inning is full of question marks. Adding one or two proven arms, preferably with swing-and-miss, is a non-negotiable part of this offseason. Too many winnable games turned stressful last year, and this team can’t continue living that close to chaos.
Reshape the outfield — and make a real decision about the kids
Grisham’s return gives the Yankees a veteran center fielder coming off a breakout offensive year. It also creates questions. A Bellinger deal would instantly change how opposing pitchers game-plan the heart of the order. If they sign him, what does that mean for Dominguez and Jones? If they can't resign him, there are still the same questions. The Yankees need to build clarity into the outfield now instead of improvising in April. A contending roster shouldn’t be trying to find itself on Opening Day.
Patch up the rotation depth before injuries take over
Max Fried tops the rotation, with Will Warren, Cam Schlittler and Luis Gil behind him — and that’s all the Yankees can count on early. Gerrit Cole and Carlos Rodon are expected to begin the season on the injured list, and Clarke Schmidt may not return from Tommy John surgery until late in the year, if at all. Ryan Yarbrough re-signed to swing between roles, but he can’t be the only safety net. The Yankees have been linked to multiple options, from past success stories like Michael King to new imports like Tatsuya Imai — and they need at least one of them.
The Yankees don’t need to overhaul their identity — just reinforce it. Add bullpen teeth. Bring in an outfield bat that fits the moment. Secure one more reliable starter. If they deliver those answers, 2026 can look like a real chase. If they don’t, this version of the Yankees could run out of time trying to figure out what it wants to be.
