Yankees Rumors: Red Sox interest in Devin Williams is nightmare waiting to happen

History repeating itself isn't always a good thing. It can be like a recurring nightmare, one that torments you night after night, refusing to allow you to find a sense of peace. That's what the latest rumor surrounding Devin Williams could become for the New York Yankees.

Williams, of course, was expected to turn the Yankees' bullpen from a strong unit, one that finished sixth in ERA (3.62) in 2024, into an elite one. Instead of locking down the ninth, however, he was quickly demoted, falling lower and lower down the leverage totem pole as the season wore on.

At the end of it, the Yankees probably regret the trade that brought him here. Watching him walk isn't the worst thing in the world. Watching him walk to the Boston Red Sox might be, though, and Boston is reportedly showing early interest in making it happen.

The Red Sox's interest in Devin Williams is setting the stage for an Aroldis Chapman-like nightmare for the Yankees

Aroldis Chapman lasted much longer in the Bronx than Devin Williams, but by the end, his descent was much the same. The once-elite closer had fallen to a 4.46 ERA, not much better than the 4.79 mark Williams posted in 2025.

The main difference between the two debacles is that the soft-spoken Williams said and did all the right things, while the volatile Chapman missed games due to an infected tattoo and was left off the postseason roster after he skipped a mandatory workout.

Chapman rebounded after leaving the Bronx, but still wasn't the fearsome force he had been during his days with the Cincinnati Reds and his early Yankees tenure. However, landing in Boston last winter seemed to revitalize him, with the erratic lefty posting the best season of his career, highlighted by a razor-thin 1.17 ERA.

Chapman's comments that he'd rather retire than play for the Yankees again show there's still a lot of animosity on his side of the equation, and perhaps that's likely what drove his late-career resurgence in Boston.

Williams doesn't seem to have that same sort of fiery personality, nor does it seem like he has any ill-will towards the Yankees, though who really knows what's going on in his heart of hearts. What is for sure is that in the hot stove's early going, a lot of teams are sniffing around him, which should leave you to believe that a lot of baseball folks believe he isn't only fixable, but that New York might have been part of the problem.

The Red Sox, clearly, are one of those clubs. And if they were to sign him and rehabilitate him, they could find themselves with an elite setup man paving the way for Chapman to unleash his rage on the Yankees 13 times a year. If things end up playing out that way, the Yankees could be looking at a lot of seven-inning affairs when they take on Boston in 2026.