Can Yankees find way back to World Series? Targets, trade chips as N.Y. keeps trying to win around Aaron Judge

At least in the regular season, the Yankees did about as well without Juan Soto in 2025 as they did with him in 2024. They won the same number of games (94) and finished with a better run differential (plus-164 vs. plus-147), and their Plan B moves worked out very well. Max Fried was excellent, so was Cody Bellinger, and Paul Goldschmidt and Devin Williams were impactful at times.

An ALDS loss to the Blue Jays followed, however, leaving the Yankees still seeking their first World Series title since 2009. To put it another way: Aaron Judge is still looking for his first World Series ring. Judge is the game’s most dominant offensive force since Barry Bonds, but he will turn 34 in April. The Yankees are running out of years to win a title with him at his peak.

“The job is always to try to find ways to get better,” GM Brian Cashman said last month. “… The job is to collect as much talent as you possibly can that you think can help your manager and his coaching staff and that team to navigate a really difficult long season, and find a way to punch your way through. I think we have a lot of good, but the job is to try to make it better.”

The Yankees finished 2025 with a $319 million payroll for competitive balance tax purposes, per Cot’s Baseball Contracts. That was third highest in baseball. Including arbitration projections, they have about $258 million on the books for 2026. Even if payroll doesn’t increase (it didn’t from 2024 to 2025), the Yankees have plenty of money to spend this winter.

What do the Yankees need this offseason? Who could they target? Who could they move? Let’s dive into that now in our offseason preview for the Bronx Bombers.

Needs

It starts in the outfield now that Bellinger and Trent Grisham are free agents. Grisham could accept the qualifying offer, but even if he does, the Yankees could bring in another veteran outfielder to lengthen the lineup. As it stands, they have Judge and erstwhile top prospect Jasson Domínguez penciled into the corner outfield spots, and no MLB-ready center fielder in the organization.

The Yankees also must strengthen the bullpen and, truth be told, this process started at the trade deadline. Deadline pickups David Bednar, Jake Bird, and Camilo Doval are all under team control through at least 2026. New York’s bullpen was its weakest in years though, and Williams and Luke Weaver becoming free agents takes away two of manager Aaron Boone’s most trusted options.

Injuries created a short-term need at shortstop (Anthony Volpe had shoulder surgery) and in the rotation (Carlos Rodón had elbow surgery). Both are expected back in the season’s first few weeks, but stopgaps are necessary. In Volpe’s case, the Yankees could target a long-term replacement this offseason, though it seems unlikely. The bullpen and outfield are the most pressing matters.

Possible targets

The Yankees used a good deal of their trade capital at the deadline and they rarely trade their very best prospects. That figures to make it difficult to swing an impactful deal this offseason, though not impossible. As for free agency, the question is always “do they want him” with the Yankees, not “do they have money to spend.” They can match any team’s financial might.

I would not call a Bellinger reunion inevitable but it does feel likely. He had a terrific season in New York, one that saw him hit his most home runs (29) and post his highest WAR (5.1) since his 2019 NL MVP season. Bellinger also seamlessly bounced between the three outfield spots and first base. His versatility and lefty bat fit the roster well. Over the last two years, Bellinger has a .919 OPS at Yankee Stadium and a .729 OPS everywhere else. Staying with the Yankees makes sense for him too. That said, as a Scott Boras client, expect Bellinger to follow the money, not necessarily the best fit.

You have to go back to DJ LeMahieu in 2019 for the last time the Yankees signed a free-agent position player away from another team with a multi-year contract. They’ve spent plenty of money to retain their own hitters (Judge, most notably), but it’s been a while since the Yankees made a big free-agent splash on the position player side. That isn’t to say the Yankees won’t make a play for Kyle Tucker, the offseason’s top free agent, just that if they do sign him, it will go against how they’ve spent their free-agent dollars the last half-decade or so. Tucker would have to slide to left field in deference to Judge, which is a small consideration more than a dealbreaker. His lefty contact skills and power would boost the offense significantly.

The Yankees did not want to trade Michael King two winters ago. They only did so because that’s what it took to get Soto. A reunion with King this offseason would check a lot of boxes. He could step right into the rotation, the Yankees know he can work out of the bullpen if necessary and there are no questions about how he’d fit into the clubhouse or New York. Shoulder and knee injuries this summer, plus the fact King is attached to draft pick compensation via the qualifying offer, could push the Yankees in another direction. On the field, though, King fits well with what the Yankees need this winter.

Given the state of the farm system, trading for Tigers lefty Tarik Skubal would be a challenge for the Yankees. They could have the pieces to swing a deal for Twins ace Joe Ryan, however, and that may be their preferred path since Ryan has two years of control compared to Skubal’s one. Ryan’s analytically friendly low arm slow and “rising” fastball does not align with New York’s preferences (they love sinkers and changeups/splitters), though I suspect they would make an exception for him. Minnesota sold hard at the deadline and there’s no reason to think Ryan will be off the market this offseason. If the Twins are willing to accept prospects in the lower minors rather than MLB-ready pieces, the Yankees would be a serious contender for the righty.

The Yankees have been connected to Pete Fairbanks at various points the last few years and were reportedly close to acquiring him from the Rays at the 2024 deadline. Tampa declined his $11 million club option last week, so now no trade is required. Fairbanks is a free agent. New York’s bullpen had the second-lowest average fastball velocity this past season, better than only the Rangers. Fairbanks and his triple-digit heater would help fix that problem. Will the fairly significant strikeout rate decline over the last two years scare the Yankees away? Or do they see that as fixable?

Possible trade chips

It’s possible the Yankees will bring both Bellinger and Grisham back. If that happens, does it make Domínguez a trade candidate? It would only make sense to listen. If not, another year of the four-man outfield rotation that worked so well in 2025 could be in the cards. There would be a trade market for plug-and-play No. 4-5 starter Will Warren given his five years of cheap control.

Some teams hoard pitching prospects. Not the Yankees. They keep who they consider their best (Cam Schlittler, etc.) and trade the rest for MLB help. The Yankees have two top 100 pitching prospects in righties Carlos Lagrange and Elmer Rodriguez-Cruz, plus 2024 first-rounder Ben Hess is a 2026 breakout candidate. One or more of these prospect pitchers could be moved.

My sense is the Yankees do not have any untouchables in the farm system, though they would have to be blown away to deal top prospect and shortstop George Lombard Jr. The rest of the league may not value power-hitting outfielder Spencer Jones as much as the Yankees given his strikeout issues. Domínguez is the most intriguing name here. Then it’s the pitching prospects.