With the offseason underway, the first order of business for the New York Yankees is to be active in free agency to keep their World Series window open next season. That’s non-negotiable.

The team needs a backup catcher, solutions at second and third base, a potential center fielder to platoon with Spencer Jones, and more bullpen depth, with several relievers hitting the open market. However, free agency is just one way for general manager Brian Cashman to fill those various roster needs.

He could also look to the trade market, which wouldn’t be a bad idea given the overall talent in this year’s free-agent class. Jack Curry of YES Network told Michael Kay on ESPN New York on Wednesday 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.”

The Yankees don’t need a blockbuster trade per se. They actually need to be creative and find a few low-cost trade targets that could get them past the Tampa Bay Rays, who won the AL East and the pennant.

Below, we’ll highlight a few players who should be on Cashman's and manager Aaron Boone’s radar this winter.

1. Willi Castro

Throughout the regular season, we wrote about how Castro should be a target for New York ahead of the August trade deadline. The 29-year-old super utilityman surprisingly didn’t get moved by the Colorado Rockies, but one has to believe that they’d be open to moving him again for the right deal.

Castro can play across the diamond—all three outfield spots and every infield position except pitcher (even though he’s done it before) and catcher, which should appeal to a team like the Yankees, especially with Amed Rosario being a free agent.

This season with the Rockies, the veteran utilityman slashed .260/.331/.417 with 15 home runs, 56 RBIs, and a .748 OPS. The 15 homers and 56 RBIs are career highs for Castro, who played in a hitter-friendly ballpark (Coors Field), and he took advantage of it.

Castro hit .309 with seven home runs, 28 RBIs, and a .836 OPS at Coors (56 games), but hit .215 with eight home runs, 28 RBIs, and a .669 OPS on the road (64 games).

That said, if the Yankees acquired Castro, he’d play in another hitter-friendly park, Yankee Stadium, which has a short porch. According to Spotrac, Castro is scheduled to make $7.3 million in 2027, which isn’t cheap, but it isn’t expensive for a player with the defensive versatility to play all over the field.

The Yankees wouldn’t have to give up a top prospect, or even Ryan Weathers or Will Warren, for Castro. A team like the Rockies, still in rebuild mode, would take a lower-level prospect in return for the veteran infielder.

2. Freddy Fermin

If the Yankees can’t get Ryan Jeffers this offseason, who received the qualifying offer from the Minnesota Twins, and they aren’t thrilled with the free-agent catcher options, a trade for Freddy Fermin could be appealing.

The 31-year-old Venezuelan catcher would be an ideal backup to Austin Wells because of his defensive work behind the plate. This season with the Padres, Fermin ranked in the 93rd percentile in blocks above average (10) and in the 97th percentile in caught stealing above average (6), per Baseball Savant.

He’s also ranked in the 72nd percentile in framing (3). He’d be an immediate upgrade over Ali Sanchez and J.C. Escarra. The Padres are set at catcher for the foreseeable future with Ethan Salas and Luis Campusano, who are both younger than Fermin.

Since Fermin is arbitration-eligible this offseason and won’t hit free agency until 2030, the Yankees might need to include a notable trade chip like Will Warren, Ryan Weathers, or Elmer Rodriguez, who could easily slot into San Diego’s rotation, in a potential deal.

3. Riley O’Brien

We couldn’t end this list without talking about a reliever. If the Yankees bring back David Bednar this winter, they still need more options, especially with Paul Blackburn not guaranteed to return this offseason.

Enter Riley O’Brien, who served as the Cardinals’ full-time closer this season, recording 38 saves, with one hold and eight blown saves in 66 appearances.

With the Yankees, the 31-year-old reliever would be a solid setup man in the eighth inning and could save games if Bednar isn’t available.

New York reportedly expressed interest in O’Brien and JoJo Romero ahead of this summer’s trade deadline, but obviously that didn’t lead to a deal. As we know, O’Brien stayed in St. Louis, while Romero was acquired by the Milwaukee Brewers, helping them win a World Series title.

O’Brien had a 4.08 ERA, which isn’t spectacular for a closer, but he held opponents to a .227 average, despite his hard-hit rate jumping from 35.0 in 2025 to 42.4. 

Looking at his splits, the right-handed reliever was better in medium (.173 OBA) and low (.233) leverage spots compared to high leverage situations (.246).

That said, O’Brien has a solid four-pitch mix, including a sinker that can get up to 97.7 mph, but batters have had success against it (hitting .279 off it), per Baseball Savant. Since he isn’t arbitration-eligible until 2028 and won’t become a free agent until 2031, the Yankees would have to consider giving up Will Warren/Elmer Rodriguez and Ryan McMahon, or maybe a prospect, to make a deal work with the Cardinals.

If his name resurfaces in trade rumors again this offseason, the Yankees should definitely see what it would cost to bring him to the Bronx.