NEW YORK —The Yankees finished 94-68 in 2025. They beat the Red Sox in the Wild Card round before falling to the Blue Jays in the ALDS.
Now two months into the offseason, the Yankees have taken heat for their lack of major moves. Their AL East rivals have been busy. The Blue Jays signed Dylan Cease for $210 million. The Orioles landed Pete Alonso for $155 million. The Red Sox traded for Willson Contreras.
Cody Bellinger remains the priority. Cashman has said so repeatedly. But there was no action in sight except adding depth pieces while fans wait for the big fish.
Meanwhile, Aaron Judge is 33. His prime years are being wasted by the Yankees.
One under-the-radar signing is listed as the player who could change the conversation. The connection is closer than most fans realize. And it involves a player the Yankees already signed this winter.
A familiar name surfaces in trade rumors
Bleacher Report’s Zachary D. Rymer recently examined free agents with buy-low upside. One name stood out for the Yankees: Willi Castro.
The 28-year-old utility man is coming off a rocky finish. He hit just .170 with the Cubs after a midseason trade from Minnesota. That number scared some teams away.
But the Yankees have reason to look past the slump. Castro has something no other free agent can offer them.
The family bond that could seal the deal
Castro is married to Aniana Rosario. She is the sister of Amed Rosario, the Yankees infielder who re-signed on a $2.5 million deal earlier this offseason.
The two players have known each other since 2012. They trained together in the Dominican Republic before signing their first professional contracts. Castro went to Cleveland. Rosario signed with the Mets.
Their bond grew stronger when Castro married into the family. The couple welcomed their first daughter, Arantxa, in December 2019. They have since added a second daughter, Amira, and are expecting their third child in early 2025.
During the 2020 pandemic shutdown, Castro and Rosario lived together in Tampa. They trained together. They cooked together. They played video games together. The experience forged a relationship that goes beyond baseball.
Now there is a chance to reunite them in pinstripes.
What makes Castro so valuable
“As a defensive presence, though, there aren’t many players who can match the sheer usefulness of Castro,” Rymer wrote. “He can play all three outfield spots and three positions on the infield, leaving only first base, catcher and pitcher as positions he can’t be counted on to cover.”
Castro made history in 2024. He became the first player in MLB history to start at least 25 games at five different positions in a single season. That versatility earned him his first All-Star selection with Minnesota.
He hit .247 with 12 home runs and 60 RBI that year. He played second base, third base, shortstop, left field and center field. He even pitched in blowout games.
The Yankees are still chasing Cody Bellinger as their top outfield target. But if the Bellinger sweepstakes drags on, Castro offers insurance at multiple spots. And if Bellinger signs elsewhere, Castro becomes an even more attractive fallback.
The 2025 season tells two different stories
Castro started 2025 on fire. He hit .245 with 10 home runs and nine stolen bases in 86 games for the Twins before the trade deadline. His .837 OPS against left-handed pitching caught the Cubs’ attention.
Chicago acquired him on July 31 for Double-A pitchers Ryan Gallagher and Sam Armstrong. The move was supposed to boost their playoff push.
It backfired. Castro hit just .170 with a .245 on-base percentage in 110 plate appearances with the Cubs. The steep drop raised questions about his consistency.
But his career numbers paint a different picture. Castro owns a .245 batting average with 55 home runs over seven MLB seasons. He stole 34 bases in 2023 alone. When comfortable, he produces.
Playing alongside his brother-in-law might be exactly the comfort he needs.
How Castro fits the Yankees’ needs
The Yankees finished second in the AL East with a 94-68 record in 2025. They beat the Red Sox in the Wild Card round before falling to the Blue Jays in the ALDS.
Brian Cashman has been linked to several big names this winter. Bellinger tops the list. Kyle Tucker and Bo Bichette have also been mentioned. But the roster needs depth pieces too.
Castro fills that role. He is a switch-hitter who can play second base, third base, shortstop, left field, center field and right field. He has even pitched in blowout games.
Manager Aaron Boone suggested the team may use Rosario at first base in 2026. Castro could provide the same kind of flexibility elsewhere on the diamond.
MLB Trade Rumors projected Castro to land a two-year, $14 million contract this offseason. That price tag fits the Yankees’ current spending approach. They have focused on smaller deals while waiting for the Bellinger and Tucker markets to develop.
Competition heats up for Castro’s services
The Yankees are not alone. Rymer also named the San Diego Padres and Seattle Mariners as teams that could pursue Castro. ESPN reported the Braves, Pirates and Rockies have shown interest as well.
Castro offers value to any contender. His playoff experience matters. He appeared in 13 postseason games during his time with Minnesota.
The Bellinger situation could determine whether the Yankees make a serious push. If Bellinger signs elsewhere, Castro becomes a more attractive fallback. If Bellinger returns, Castro could still provide bench depth.
Either way, the family connection makes the Bronx a natural fit. Playing alongside his brother-in-law in pinstripes could be the deciding factor.
What do you think?
