The Yankees have work to do this winter, and the path forward may not be limited to free agency. Brian Cashman still has to patch multiple holes, but the trade market could give New York a cheaper way to get there.
That matters because the list of needs is long. The Yankees need a backup catcher, help at second and third base, a possible center fielder to pair with Spencer Jones, and bullpen depth with several relievers headed for free agency. Jack Curry of YES Network said Wednesday on ESPN New York that “the Yankees are going to be creative and they're going to figure out a way to fill some of these voids and some of these needs via the trade route.”
That kind of creativity could point the Yankees toward a few lower-cost targets rather than a splashy move. Three names stand out: utilityman Javier Castro, catcher Freddy Fermin and reliever Riley O’Brien.
Castro is the type of player who can quietly solve a lot of problems. The 29-year-old can handle all three outfield spots and every infield position except pitcher and catcher, which gives a roster plenty of flexibility. That versatility should matter to the Yankees, especially with Amed Rosario set to hit free agency.
Colorado never moved Castro before the August deadline, but there’s reason to think the Rockies would listen again. He just posted a .260/.331/.417 line with 15 home runs, 56 RBIs and a .748 OPS. Those 15 homers and 56 RBIs were career highs.
The split tells the story. At Coors Field, Castro hit .309 with seven homers, 28 RBIs and an .836 OPS in 56 games.
On the road, he hit .215 with eight homers, 28 RBIs and a .669 OPS in 64 games. Yankee Stadium’s short porch could make him a fit in another hitter-friendly environment.
He’s scheduled to make $7.3 million in 2027, per Spotrac, so he’s not a bargain-bin player. Even so, he’s not the kind of asset that should cost New York a premium prospect. A lower-level prospect could be enough for a Rockies team still in rebuild mode.
If the Yankees miss on Ryan Jeffers, who received the qualifying offer from the Minnesota Twins, and don’t love the free-agent catching market, Fermin becomes a logical fallback. The 31-year-old Venezuelan catcher would give Austin Wells a strong defensive backup.
Fermin’s glove is the selling point. This season with the Padres, he ranked in the 93rd percentile in blocks above average with 10 and in the 97th percentile in caught stealing above average with 6, according to Baseball Savant.
He also ranked in the 72nd percentile in framing with 3. That would be a clear upgrade over Ali Sanchez and J.C.
Escarra.
The Padres have Ethan Salas and Luis Campusano, both younger than Fermin, so they’re set at catcher for the long haul. But because Fermin is arbitration-eligible this offseason and won’t reach free agency until 2030, a deal could require a meaningful return. Will Warren, Ryan Weathers or Elmer Rodriguez could be the kind of piece San Diego would want, with Rodriguez able to fit into the rotation.
The bullpen search brings another name into the mix. Even if the Yankees bring back David Bednar, they still need more relief help, especially with Paul Blackburn not guaranteed to return.
Riley O’Brien fits that need. The 31-year-old served as the Cardinals’ full-time closer this season and finished with 38 saves, one hold and eight blown saves in 66 appearances. In New York, he could work as a setup arm in the eighth inning and still cover games when Bednar isn’t available.
The Yankees were linked to O’Brien and JoJo Romero before the trade deadline this summer, but no deal came together. O’Brien stayed in St. Louis, while Romero landed with the Milwaukee Brewers and helped them win a World Series title.
O’Brien’s numbers are solid, if not flashy. He posted a 4.08 ERA and held hitters to a .227 average, even though his hard-hit rate climbed from 35.0 in 2025 to 42.4. He was better in medium leverage situations, where opponents hit .173, and in low leverage, where they hit .233, than in high leverage, where they hit .246.
There’s real stuff here, too. O’Brien works with a four-pitch mix, and his sinker can reach 97.7 mph, though hitters have done damage against it, batting .279.
He isn’t arbitration-eligible until 2028 and won’t become a free agent until 2031, so the Cardinals would have leverage in talks. New York might have to part with Will Warren, Elmer Rodriguez and Ryan McMahon, or perhaps a prospect, to make something happen.
If O’Brien’s name comes up again this winter, the Yankees should be ready to check the price.
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