5 offseason decisions the 2025 Yankees are paying for in August

The New York Yankees are suffering terribly right now as they desperately crawl towards a hoped-for postseason berth. While the team’s many acquisitions prior to the 2025 trade deadline have been an area of focus lately, the offseason moves enacted by General Manager Brian Cashman still linger in fans’ minds.

How many more games could this team have won if they had a decent infielder who can play third base? How much closer to the top of the American League East would the Yankees be if they had a starting pitcher better than everyone other than Max Fried and Carlos Rodón? What if they had not one, but two All-Star caliber players in their infield?

Here are 5 offseason decisions that decidedly did not work out in New York’s favor.

Devin Williams

Williams might be one of the most unpopular people in New York City right now. His last four outings have been disastrous, with a total of six earned runs allowed across 3.2 innings. His season as a whole has been a steep decline from his superb 2024, when he earned an ERA+ of 331. 2025 Williams has an ERA+ of 75, by far the worst of his seven-year career. Once heralded as a closer that could shut down a game with relative ease, now the sight of Williams trotting out of the bullpen inspires nothing but fear and loathing. It’s an unfortunate turn of events for the former Brewer, though manager Aaron Boone shares some of the blame for using Williams in high-leverage situations despite repeated recent failures.

Clay Holmes

Speaking of closers, Holmes was nearly chased out of town after a somewhat rocky 2024 season that in retrospect looks pretty solid compared to Williams’ 2025 performance. Last season, Holmes as a closer had an ERA+ of 129 while earning 30 saves. When he left the Bombers, he signed with the Mets as a starter. In that role, he’s posted a 113 ERA+, 1.3 WAR, and a .600% winning percentage. It’s not exceptional, but it’s better than a host of pitchers who have spent time in the Yankees’ rotation, including Marcus Stroman, Cam Schlittler, and Will Warren. If Holmes had stayed put and become a starter, the Yankees would be a stronger team.

Gleyber Torres

Torres leaving New York for the Detroit Tigers once seemed like a smart move. Given his apparent unwillingness to play third base, it was hard for New York to consistently keep both Torres and Jazz Chisholm Jr. in the lineup (and when Boone decided to play Jazz at third, it was a predictable disaster that was soon reversed).

Fortunately for Torres and unfortunately for the Yankees, the 2025 All-Star is currently rocking a 122 OPS+, his best since 2019. In an alternate timeline, perhaps New York could’ve retained Torres and spent spring training trying to make Jazz a stronger defender at the hot corner. Instead, a rotating cast of underachieving characters spent time at third before Cashman finally acquired Ryan McMahon to stop the bleeding.

Juan Soto

Yankees fans spent months trying to cast Juan Soto out of their hearts and minds after the four-time All-Star abandoned them for the crosstown rival Mets. That painful psychological process was made easier because Soto’s replacement in the outfield, Cody Bellinger, has been spectacular this season on both sides of the ball. But, at the risk of opening an old wound, it’s still true that Soto has had the better season and remains the better player.

His 4.0 WAR beats Bellinger’s 3.3, and his 147 OPS+ tops Belli’s 126. Both are exceptional, but one is a tad more exceptional than the other. Generating runs has not been the Yankees’ primary weakness this season, but higher numbers on the scoreboard always help.

Caleb Durbin

At the end of 2024, the Yankees traded Durbin and Nestor Cortes Jr. to the Brewers in exchange for Devin Williams. Both Cortes and Williams have been busts. But Durbin, who had recently spent time with the Triple-A Scranton RailRiders, has been a reliable infielder this season in Milwaukee, earning a 103 OPS+ and 2.2 WAR.

The Yankees could’ve used Durbin earlier this year when they were experimenting with a bunch of third base options, none of which panned out.