Sixteen months ago, the Yankees got creative with present and future infield needs under consideration. Their second baseman was underperforming and hot corner was a black hole. Gleyber Torres was normally
a reliable offensive presence but was slumping in the first half of his walk year while DJ LeMahieu and Oswaldo Cabrera combined did not add up to a major league third baseman.
The Yankees solved that issue by trading for Jazz Chisholm Jr. days before the deadline, the incoming Marlin providing an above-average bat at third (and as luck would have it, an elite glove as well). Additionally, his extra years of team control allowed the Yankees to let the then-struggling Torres walk in free agency as Jazz could slide back to his more natural second, thus upgrading the hot corner offensively in 2024 and the keystone in 2025 (acknowledging that Torres turned it around in the second half and was one of the team-carrying postseason bats on the way to the World Series).
The Yankees have a similar opportunity for some creative roster building this winter with reports that the Cardinals are willing to listen to offers on many of their players — most importantly, Brendan Donovan.
2025 Statistics: 118 games, 515 PA, .287/.353/.422, 10 HR, 50 RBI, 119 wRC+, -1 Outs Above Average, 2.9 fWAR
2026 FanGraphs Depth Charts Projections: 136 games, 588 PA, .279/.353/.411, 13 HR, 57 RBI, 117 wRC+, 3.1 fWAR
Contract Status: Lost 2025 arbitration case — played on one-year, $2.85 million contract. Entering second year of arbitration eligibility, free agent after 2027 season
Donovan has long been a pipe dream acquisition for many around these boards, myself included. He was immediately successful in his 2022 debut, logging a 127 wRC+ and 2.6 fWAR in 126 games, and his multi-tool skillset and many years of inexpensive team control made him one of the holy grail trade targets. It is perhaps that tantalizing mix of ability and control that made him so unattainable, along with the Cardinals’ intention to build around him as one of the foundations of a young core.
Fast forward three years and that core never materialized in St. Louis, and now with demolition man Chaim Bloom taking the reins from John Mozeliak, the expectation around the industry is that the Cardinals roster is ripe to be blown up this winter. Unfulfilled expectation is a tag that in some ways can also be applied to Donovan, the second baseman always seeming on the cusp of breaking into the star tier of player before injuries cut a promising campaign short. He played 95 games in 2023 before undergoing season-ending flexor tendon surgery, and he missed the final six weeks of 2025 with a groin injury and underwent sports hernia surgery at the conclusion of the season.
It’s hard to believe, but he is already entering his age-29 season with just two years of team control remaining. That being said, he remains one of the best second baseman in the league when he is on the field. Among the players with at least 400 plate appearances at the position, Donovan ranked third in average (.287), fifth in wRC+ (119), and tied for seventh in fWAR (2.9). FanGraphs’ Depth Charts project system thinks he can repeat these results in 2026, projecting him as a top-six second baseman in terms of wRC+ (117) and fWAR (3.1).
You might be wondering how this all involves the Yankees if they already have a star second baseman in place for 2026. It’s also unlikely that they would move Jazz over to second to accommodate an incoming player considering the trade they made to acquire Ryan McMahon and his two remaining years under contract as well as how poor Jazz was defensively at the hot corner to start 2025.
Acquiring Donovan gives them a readymade replacement at the keystone that would make it easier for them to let Jazz walk in free agency after the upcoming season just as they did with Torres. Jazz has expressed a desire to remain a Yankee beyond next season, but Brian Cashman recently revealed that they have not held extension talks. The Yankees generally don’t do extensions with arb-eligible players, especially after getting burned on the Luis Severino and Aaron Hicks extensions.
The creative part comes with getting Donovan into a lineup that already has Jazz and McMahon entrenched as starters. He has logged 106 major league innings at shortstop at a roughly league-average level, and they need a starting shortstop with Anthony Volpe expected to miss the start of the season as he recovers from shoulder labrum surgery. This allows the Yankees their preference of keeping José Caballero as a base running threat off the bench, and if Donovan is raking when Volpe is healthy there’s no rush to reincorporate the fourth-year shortstop who appears to already be bumping his head on a disappointingly low offensive ceiling.
It’s an unrealistic scenario given the amount of blind faith Cashman and Aaron Boone continue to show in Volpe, but doesn’t rule out a Donovan acquisition altogether. He has also logged innings at third and the outfield corners, so there’s an opportunity for a Swiss Army role like they initially envisioned for LeMahieu. These all require a lot of moving parts internally, to say nothing of the prospect cost it would require to pry Donovan from St. Louis. He has remained steadfast publicly in his desire to remain with the Cardinals. However, he is approaching his thirties, a massive rebuild is incoming in St. Louis, and there may be lingering resentment over the arbitration hearing last winter and the rumors of the new GM shopping him upon taking office. The Yankees have had their eyes on Donovan for four years now, and there may never be a better time to get him in pinstripes than this winter.
