Yankees checklist for 2025 MLB Winter Meetings: Breaking down the biggest needs

The Yankees’ offseason, so far, has been uneventful.

Aside from some minor signings, and one big qualifying offer being accepted, New York has yet to fill out its roster to try to get back to the World Series. While division rivals like the Red Sox and Blue Jays have already made big splashes, Yankees GM Brian Cashman is seemingly biding his time. While the team’s needs and priorities are very obvious, the Yankees enter the MLB Winter Meetings with a lot of questions and even more work to do.

Here’s a checklist of what the Yankees need to do this week during the Winter Meetings in Orlando…

Bring Cody Bellinger back

The biggest offseason move the Yankees need to make is to re-sign Bellinger. Cashman got a steal when he made the trade with the Cubs last offseason to bring the former NL MVP to The Bronx. Bellinger had one of his best seasons as a pro and helped the Yankees lengthen the lineup and shore up the defense in the outfield. He won games single-handedly with his defense alone this past season and has proven that he’s perfect for the pinstripes.

It’s clear Bellinger is Cashman’s priority this offseason, just as Juan Soto was a year ago. And while that pursuit didn’t pan out, Cashman can’t possibly allow Bellinger not to return, especially when teams like the Dodgers and Mets are vying for his services.

It won’t be easy, Bellinger — who is represented by Scott Boras — will look to have a lucrative multi-year deal and the Yankees may have to go further than they otherwise might be comfortable with; that’s how important Bellinger is to the 2026 Yankees. Aaron Judge and Trent Grisham can’t be the only veterans in the outfield next season while they try to capture lightning in a bottle with Jasson Dominguez or Spencer Jones. 

Enact Plan B if Bellinger leaves

This offseason is becoming eerily similar to last year. Soto took the money to go to the Mets and Cashman had to pivot, and pivot he did.

Cashman traded for Bellinger and Devin Williams while signing Max Fried. The GM’s moves worked and helped the Yankees tie the Blue Jays for the best record in the American League. Now, what could Cashman do for an encore?

If the Yankees can’t re-sign Bellinger, Cashman needs to be ready to enact his Plan B. Whether that’s signing Kyle Tucker or trading for an outfielder like Steven Kwan, the longtime GM has to show the fans that if Bellinger doesn’t come back, the outfield will be just fine.

Cashman has to be creative; he’s done it before, and he may need to do it again. Hopefully, he’s prepared.

Fill out the bullpen

Two moves the Yankees have made this offseason are re-signing Ryan Yarbrough and picking up Tim Hill’s option, which helps fill holes in the bullpen, but there’s still work to be done.

Devin Williams is gone and Luke Weaver is still a free agent. Cashman and the organization have been great at creating a bullpen in the past and I expect this year to be the same. Perhaps a reunion with Weaver is on the way, or signing former Padres closer Robert Suarez to pair with David Bednar is a possibility. And, who knows, perhaps a trade could happen in the same way Williams was acquired.

Figuring out the outfield is the priority for the Yankees, but finishing up the bullpen is second on the list and Cashman needs to address it soon.

Get greedy and sign a starter

The Yankees’ starting rotation is set … when it’s healthy.

Gerrit Cole and Carlos Rodon will miss the start of the 2026 season, but they will be back. But there may be questions about their effectiveness when they do return. Cashman and the Yankees also have to wonder if they can fully trust the trio of Luis Gil, Will Warren and Cam Schlittler for another season.

The Yankees can give themselves some comfort by splurging on another starter either in free agency or via trade.

There are some intriguing buy-low, reclamation projects like Zac Gallen or Merrill Kelly who can shore up the back of the rotation. Miami has controllable starters like Sandy Alcantara and Edward Cabrera that can be traded for as well. The rotation is definitely low on the list of priorities for the Yankees, but with so many question marks, it can’t hurt to have as many starters as possible and if Cashman brings one in, the younger arms become trade pieces for the aforementioned outfielder.

Dispel all payroll questions

Heading into the Winter Meetings, there’s been a lot of chatter about the Yankees’ 2026 payroll and whether or not Hal Steinbrenner is willing to go over $300 million, including comments from Steinbrenner himself. They currently sit at around $283.6 million (after taxes), so there’s not a lot of wiggle room for the Yankees if they hope to improve their team.

I find it hard to believe the Yankees would operate below $300 million, so Cashman could show the baseball world — and Yankees fans — that they are ready to spend this offseason by signing a Bellinger or a handful of names. Not to rush the process, but leaving the Winter Meetings without a deal done would not quell fears. It’ll be even worse if targets like Bellinger and Tucker sign elsewhere.