NEW YORK, NY – OCTOBER 01: Devin Williams #38 of the New York Yankees looks on before the game against the Boston Red Sox at Yankee Stadium on October 1, 2025 in New York, New York. (Photo by New York Yankees/Getty Images)
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Last winter, facing the exodus of some key players, the New York Yankees pulled off a stunning blockbuster trade that drove plenty of optimism among the fanbase.
With reigning All-Star closer Clay Holmes reaching free agency, the Yankees brought in two-time National League Reliever of the Year Devin Williams in a transaction with the Milwaukee Brewers. Williams immediately became the favorite to pitch in the ninth inning for the Yankees and it was easy to imagine him leading the bullpen into a deep playoff run.
Unfortunately, things didn’t quite work out that way.
Williams struggled in high-leverage situations for the Yankees and was booed by the fan base as he failed to close out games in the regular season. By the trade deadline, he lost any potential role as a closer for the team to David Bednar, who was acquired from the Pittsburgh Pirates.
Now Williams is a free agent and a return to the Bronx seemed virtually impossible. However, it turns out Williams is getting a surprising amount of interest on the open market after his brutal season and the Yankees have reportedly decided to engage with his camp about a potential reunion.
“The Yankees and the camp for free agent late-inning reliever Devin Williams recently discussed the potential for a possible reunion, league sources said,” according to Ken Rosenthal and Will Sammon of The Athletic. “Williams is garnering widespread interest, but the Yankees have at least maintained contact with the right-hander after he spent an up-and-down 2025 season in the Bronx.”
Williams has also been connected to the Los Angeles Dodgers, Cincinnati Reds, Boston Red Sox and New York Mets this winter, so a return to the Yankees is far from a sure thing. However, the fact that the two sides are even considering the possibility is a significant shock, given just how poorly Williams’ tenure went this past season.
“The Yankees and Williams won’t say that, but both know his odds of a 2026-and-beyond reunion are about the same as Mariano Rivera coming out of retirement to close games next season at age 56,” as Yankees insider Randy Miller put it for NJ.com shortly after the season ended. “After a December 2024 deal, the fit between Williams and New York never materialized. It was broken from the start — and his performance never recovered either.”
The Yankees and Williams seem like they’d be better off by parting ways this winter. It was pretty clear that the New York spotlight had a negative impact on the pitcher and that’s unlikely to change. But as the two sides explore the potential for a reunion, perhaps what was once all but impossible and certainly remains ill-advised could become a reality for next season.
Source: https://www.forbes.com/sites/peterchawaga/2025/11/20/yankees-make-shocking-devin-williams-decision-after-brutal-season-report/
