By admin 
The New York Yankees don’t have obvious solutions to some of their weaknesses. In particular, finding an upgrade at third base will be a challenge.
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It’s extremely clear that the Yankees cannot rely on Ryan McMahon anymore. His defense has been highly disappointing, and his bat is even worse. Unfortunately, the Bronx Bombers don’t have any internal options to replace him, and there are barely any appealing options at the hot corner in free agency.
Not counting Teruaki Sato (who is expected to be posted this winter), the best available third baseman on the open market is probably Alec Bohm, who was mediocre at best this season. And while Sato is coming off a tremendous season in NPB, concerns about his defense and plate discipline make him far from a sure thing.
As a result, the Yankees may need to scour the trade market for a third baseman. However, they need to have learned from their previous mistakes when searching for an upgrade.
The Yankees must avoid taking on bad contracts in a trade
The Yankees’ last two attempts to upgrade at third base were trades for the aforementioned McMahon at last year’s trade deadline and Josh Donaldson during the 2021-22 offseason. They also played Jazz Chisholm Jr. at third base after acquiring him at the 2024 trade deadline, but moved him back to second base after Gleyber Torres left in free agency.
In both cases, New York chose to take on the majority of their contracts. Donaldson had two years left on a four-year, $92 million contract with an $8 million buyout on a $16 million team option for 2024. McMahon is under a six-year, $70 million contract. The Rockies retained some salary in 2025, but the Yankees are responsible for paying him $16 million in 2026 and 2027.
Of course, both trades ended up being monumental flops on the field. Donaldson was outright released before the 2023 season ended, and McMahon is likely trending in the same direction. Another issue further exacerbating things for both guys was their contracts, which limited the Yankees’ flexibility in free agency.
After the Twins traded Donaldson to New York, they promptly signed Carlos Correa. Despite his injury history, Correa was a top shortstop who later moved to third base. If the Yankees pursued him in free agency instead of trading for Donaldson, they could have played him at shortstop in 2022 before moving him to third base in 2023 to accommodate Anthony Volpe. Instead, they had to deal with a below-average season from Isiah Kiner-Falefa at shortstop on top of Donaldson’s poor play.
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Similarly, trading for McMahon and taking on his contract led to the Yankees doing next to nothing in free agency the following winter, outside of bringing Cody Bellinger back.
However, they could have pursued Kazuma Okamoto or Alex Bregman in free agency if they hadn’t committed to McMahon. Okamoto’s offensive prowess outweighs McMahon’s glove, while Bregman is a sure-handed defender at the hot corner and one of the best-hitting third basemen in the league.
Even though third base is the example here because of how long it has been a glaring weakness for the Yankees, this logic applies to any trade the team considers this offseason.
The Yankees have already committed $100+ million in contracts to Aaron Judge, Giancarlo Stanton, Gerrit Cole, Max Fried, Cody Bellinger, and Carlos Rodon. They still need to find a way to re-sign David Bednar in free agency and possibly extend Cam Schlittler or Ben Rice. Trading for an aging veteran on a large contract might reduce financial flexibility even more, especially with a salary cap possibly looming.
The position player market in free agency is weak, so the Yankees turning to the trade market to add bats or bullpen arms isn’t a bad idea. But if the Donaldson and McMahon trades have taught them anything, pursuing aging players on expensive contracts isn’t the right way to upgrade the roster.
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This article was originally published on www.si.com/mlb/yankees/onsi as The Biggest Offseason Mistake the Yankees Must Avoid This Winter.
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This story was originally published October 13, 2026 at 4:00 PM.