The New York Yankees have never been shy about making noise in the offseason, and according to SNY, this winter could be no different. MLB writer Anthony McCarron ranked the Yankees’ top five trade targets for the 2025-26 offseason, with the list highlighting the team’s pursuit of contact bats, bullpen depth, and possibly even another front-line starter.
Contact Hitters, Power Arms, and a Familiar Blueprint
After another early playoff exit, Brian Cashman faces the same challenge that’s defined much of his tenure: balance a power-heavy lineup with players who can make consistent contact. That’s why SNY’s list begins and ends with hitters who could alter the Yankees’ offensive approach.
At No. 1 sits Cleveland Guardians outfielder Steven Kwan, a player whose skill set contrasts sharply with the Yankees’ high-strikeout tendencies. Kwan, who batted .281 with a .330 on-base percentage and ranked among league leaders in contact rate, could finally give New York a consistent leadoff option. He’s also a defensive gem, having won four consecutive Gold Gloves in left field. His ability to get on base and set the table for Aaron Judge could be the type of low-profile, high-impact move that reshapes the Yankees’ lineup.
Still, the price would be steep. The Guardians rarely sell low, and Kwan still awaits arbitration. But as McCarron noted, “the Guardians have swapped players as they move through arbitration before.”
The rest of SNY’s top five list shows a blend of buy-low gambles and potential blockbusters. At No. 2, the Yankees are linked to Pete Fairbanks of the Tampa Bay Rays, one of baseball’s most underrated high-leverage relievers. Fairbanks notched a career-best 27 saves and 2.83 ERA in 2025, with a 97 mph fastball and slider combination that could make him an ideal setup man behind David Bednar.
High-Upside Bets in the Rotation and Bullpen
With Devin Williams and Luke Weaver headed to free agency, adding Fairbanks would help stabilize a bullpen that faltered late last season. The Rays’ $12.5 million option on him for 2026 might make a deal feasible, especially if Tampa looks to cut costs.
Starting pitching isn’t an immediate crisis, but depth could quickly become one. SNY lists Mitch Keller of the Pittsburgh Pirates at No. 4 as a possible target, noting that the Yankees could deal one of their young arms—like Luis Gil or Will Warren—to strengthen other areas. Keller, who logged a 4.19 ERA across 32 starts, could be an innings-eating insurance policy for a rotation awaiting the returns of Gerrit Cole and Carlos Rodón.
Meanwhile, SNY also floated Oneil Cruz, the Pirates’ athletic center fielder, and Adolis García of the Texas Rangers as possible options for New York’s outfield. Cruz, though raw, brings elite athleticism and power, while García remains a high-upside rebound candidate after a down season.
The Yankees’ offseason direction depends largely on whether they retain Cody Bellinger and how aggressively they pursue free agents. But one thing remains certain: Cashman and his front office will explore every trade avenue.
As McCarron put it, “Their offseason will be a fun watch, as usual.” If the Yankees can land even one of these five targets, it could set the tone for a much-needed roster reset in the Bronx.
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