The New York Yankees are going to be one of the more active teams this winter. With one of the highest payrolls in the Major Leagues, the Yankees will explore plenty of potential additions this winter.
Trent Grisham is already back, after the outfielder accepted the $22.025 million Qualifying Offer, and Cody Bellinger could still wind up returning. But one of the most important areas of the roster to address is in the bullpen.
Devin Williams is a free agent and could wind up departing for a new team. But, as Ken Rosenthal and Will Sammon of The Athletic report, the Yankees and Williams are discussing a reunion this winter.
Yankees, Devin Williams discussing free agent 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." Rosenthal and Sammon write.
New York would benefit from bringing the veteran reliever back, even though his initial stint in New York didn't go as planned.
In 2025, Williams had a 4.79 ERA with four wins and six losses across 67 games for the Yankees. His 85 ERA+ was by far the worst of any season of his seven-year MLB career.
He was a two-time All-Star with the Milwaukee Brewers, but regressed significantly once he joined the Yankees.
However, despite his struggles, the Yankees want him back. His 0.00 ERA in four outings in the playoffs is encouraging enough that the Yankees could hope that version appears for the 2026 regular season and beyond.
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He has a career ERA of 2.45, so his 4.79 ERA in 2025 is a major outlier. If he can get back to his former self from his time in Milwaukee, then Williams could wind up being a huge piece of the bullpen for a team in 2026.
The Yankees, according to Rosenthal and Sammon, are trying to make it work with Williams and his camp. The 31-year-old reliever has a strong market, giving the Yankees some tough competition.
But, with Williams open to a return and the Yankees' desire to bring him back, a reunion after a brief trip to free agency is very possible for Williams and the Yankees.
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