ORLANDO, Fla. — Brian Cashman has a proven track record of pulling off major moves at baseball’s annual winter gathering. Last December he swung a deal for Cody Bellinger. The year before that he engineered the Juan Soto blockbuster that helped the Yankees reach their first pennant since 2009.
Now the Yankees general manager arrives in Orlando with hopes of a 94-win team that fell short in the ALDS. He has roster holes to fill, prospects to dangle and a budget that might not cooperate.
The next four days could determine whether New York gets the reinforcements it needs to chase a championship.
Position player targets on Cashman’s radar
Signing Bellinger would simplify the Yankees’ winter strategy. The former MVP slashed .272/.334/.480 with 29 home runs and 98 RBIs in 2025. Bringing him back would allow Cashman to focus on depth rather than a splashy addition.
But several trade targets have emerged if the Yankees want to get creative.
Phillies third baseman Alec Bohm enters his free-agent walk year and could complement Ryan McMahon as a right-handed bat. Bohm has experience at first base and posted an .818 OPS against left-handed pitching in 2025.
Texas Rangers third baseman Josh Jung has three more years of team control after a subpar season. The right-handed hitter offers upside at a position where the Yankees need answers.
Houston’s Isaac Paredes provides power from the right side despite rocky defense. Cleveland outfielder Steven Kwan could address the lack of a true leadoff hitter despite posting an on-base percentage 18 points lower than Trent Grisham in 2025.
Minnesota’s Byron Buxton remains an option if Bellinger signs elsewhere. Kwan has two seasons of team control remaining, but any major outfield move depends on resolving the Bellinger situation first.
Pitching targets could spark blockbuster talk
The Yankees have no acute need for a top-tier starter. Gerrit Cole, Carlos Rodon and Clarke Schmidt will return from elbow surgeries at some point in 2026. Max Fried anchors the rotation. Luis Gil showed promise after returning from injury.
Still, Cashman invites all discussions. That means inquiries about the Miami Marlins’ Edward Cabrera and Sandy Alcantara remain active.
Alcantara won the NL Cy Young Award in 2022 and struggled to a 5.36 ERA in his first year back from Tommy John surgery. But he posted a 2.68 ERA over his final eight starts and carries just $17.3 million in 2026. Pittsburgh’s Mitch Keller presents another option.
Minnesota right-handers Joe Ryan and Pablo Lopez generate significant interest around the league. Both remain under team control through 2027. Milwaukee’s Freddy Peralta enters his free-agent walk year and could move.
The bullpen offers a more likely path for trades. San Diego lefty Adrian Morejon made the All-Star team and enters his walk year. The Padres might prefer to keep him in their rotation, but Cashman will check in.
Yankees players who could be moved
Jazz Chisholm Jr. enters his free-agent walk year with low chances of getting a long-term extension in New York. The dynamic second baseman posted 31 home runs and 31 stolen bases in 2025. He became just the third Yankee ever to accomplish that feat.
Chisholm is not off-limits in trade discussions. But any partner would be a contending team, and what return would match his value?
Jasson Dominguez and Spencer Jones sit at the center of most trade speculation. Dominguez disappointed in his first full season with a .569 OPS from the right side. Jones crushed 35 home runs in the minors but struck out 179 times.
Moving either prospect would likely require a blockbuster return. Someone on the level of Detroit’s Tarik Skubal, the two-time Cy Young winner entering his walk year, would be the prize. Whether such a player is even available remains unclear.
Camilo Doval could draw inquiries from teams seeking a closer. The setup man on New York’s depth chart will earn close to $7 million in 2026.
As the Winter Meetings open Sunday in Orlando, Carlos Lagrange has emerged as one of the most talked-about names on the trade market. The Yankees’ hard-throwing prospect, who has reached 102 mph, has turned into a major asset at the perfect time. His value could shape the Yankees’ future, whether he stays in the Bronx or becomes the piece that helps land a star.
Half a year ago, few inside Yankee Stadium even recognized his name. Now, Lagrange is viewed as a possible pivot point in the Yankees’ offseason planning.
The 22-year-old right hander from the Dominican Republic has surged up the organization’s evaluations throughout the year. He is now ranked second on the Yankees’ internal prospect board.
Grisham’s status adds complexity
Trent Grisham might become expendable depending on how the outfield situation shakes out. The lefty-hitting center fielder accepted the $22.025 million qualifying offer last month.
That contract comes with strings attached. Grisham cannot be dealt without his permission until June 15 due to accepting the qualifying offer. Any early move would require his approval.
Catcher J.C. Escarra is available as the Yankees seek right-handed hitting depth behind Austin Wells.
Budget battles loom over every decision
Owner Hal Steinbrenner wants to reduce the $319 million payroll from 2025. He called a lower number “ideal” and questioned whether spending correlates with championships.
“We had a good team last year,” Cashman said recently. “But it’s not the same team because of free agency. We’ll see where it all takes us.”
Aaron Judge has captured three of the last four AL MVP awards. The reigning batting champion has said he would trade all of it for a World Series ring.
Cashman delivered at the Winter Meetings in 2023 and 2024. The pressure to do it again starts now.
What do you think? Leave your comment below.
I think its time the young players get the shot they deserve. All the “trade” players talked about had to start somewhere. Let the baby bombers explode!