Red Sox Eye Surprise Blockbuster Move Targeting Devin Williams Amid Yankees’ Free Agency Frenzy

As the 2025-26 MLB offseason unfolds, the Yankees find themselves at a crossroads. With a roster situation that’s both promising and precarious, the buzz surrounding free agents and trade prospects is heating up. Devin Williams, despite a tough stretch last season with the Bombers, has drawn eyes from the Red Sox, Dodgers, and Reds — a testament to his enduring potential, albeit with a wrinkle or two in his performance stats. Meanwhile, the bullpen’s back end faces uncertainty not just with Williams but also with Luke Weaver hitting free agency, leaving the Yankees’ relief future somewhat up in the air.

On the flip side, the Yanks haven’t let injury woes dampen their interest in fresh arms. Ryan Yarbrough, who showed he can be a versatile cog last season when healthy, is reportedly on New York’s radar again. But beyond personnel, the real story might be the Yankees’ ongoing wrestle with their financial blueprint. With owner Hal Steinbrenner and GM Brian Cashman repeatedly stressing that maintaining a $300 million payroll — especially one heavy with luxury tax penalties — isn’t feasible, the team faces tough strategic decisions. Coping with this budget-conscious reality while trying to lock down key figures like Cody Bellinger — a player seen as the linchpin of their offseason — demands surgical precision in roster moves.

Joel Sherman lately spilled some inside insights, proposing the Yankees’ offseason goals: re-sign Bellinger, add a reliever who can close critical innings, find a starting pitcher to cover early-season injuries, and bolster the lineup with a right-handed bat plus perhaps bringing back Amed Rosario. In this financial juggling act, the challenge is clear — can they fit Bellinger’s estimated $27 million salary along with necessary reinforcements without tipping over the $304 million luxury tax line? If you ask me, the margin’s razor-thin, but that’s where savvy management and some good fortune come into play. The next few weeks promise to be one heck of a ride for the Bronx faithful.

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Here’s the latest Yankees free agency and trade buzz during the 2025-26 MLB offseason…

Nov. 13, 11:09 a.m.

The Red Sox are among the teams with interest in Devin Williams, reports Will Sammon of The Athletic, who also lists the Dodgers and Reds among teams that have expressed interest.

Fabian Ardaya of The Athletic also reported on Los Angeles and Williams, saying there appears to be mutual interest.

Los Angeles was one of the teams exploring the possibility of dealing for Williams last offseason before he was traded to the Yankees.

Williams, 31, struggled last season for the Yanks, posting a 4.79 ERA and 1.12 WHIP in 62.0 innings.

While Williams was not his regular elite self, his stuff still played up as he had a strikeout rate of 13.1 per nine.

In addition to Williams, Luke Weaver is also a free agent, leaving the back end of New York’s bullpen in an uncertain spot.

Nov. 12, 11:33 a.m.

A source told Gary Phillips of the New York Daily News that the Yankees have checked in on left-hander Ryan Yarbrough, and the club is “expected to be suitors” for the 33-year-old.

After signing with the Yanks last spring, Yarbrough ended up being a valuable and versatile piece for Aaron Boone‘s pitching staff. He started eight games and appeared in 19 games in total, pitching to a 4.36 ERA while holding opposing lefties to a .198 batting average.

Yarbrough did miss a significant chunk of the season, though, as an oblique injury kept him out from mid-June to early September. As a result, he was left off the Yankees’ postseason roster.

Nov. 11, 3:45 p.m.

Historically, the Yankees have been among the highest-spending teams in baseball, but owner Hal Steinbrenner and GM Brian Cashman have reiterated multiple times over the past couple of years that having a payroll over $300 million is “simply not sustainable for us, financially,” as Cashman put it.

“It wouldn’t be sustainable for the vast majority of ownership [groups], given the luxury tax we have to pay,” Cashman said last May. “I’ve been a broken record [on this topic]: I don’t believe I should have a $300 million payroll to win a championship.”

So how does that line of thinking impact what the Yankees will do this offseason?

Appearing on “Pinstripe Post,” Joel Sherman of the New York Post laid out how he believes the Yankees can thread the needle to retain a key free agent like Cody Bellinger, whom he referred to as “the key to their offseason,” while lowering their payroll beneath the $300 million number.

“I think the goal this offseason is to try to get under $300 million, luxury tax money. I think within that they’d like to re-sign Cody Bellinger, add another reliever who can pitch in the final six outs of the game… I think they’d like to find a complementary starting pitcher to help them through some injuries early in the season. I think they’d love to flip J.C. Escarra for a righty version of J.C. Escarra… and I think they’d like to find a complementary right-handed bat, and maybe plus Amed Rosario, who they liked a lot and tried in previous years to get.

“That all told, I think the Yankees would feel, if they got the versions of the players they wanted to, they would feel that’s a 90+ win team, and they’d have a shot to line it up, and that they could do that in the high ($200 millions).”

The Yankees ended last season with a payroll of $323.7 million, for luxury tax purposes. Factoring in projections for arbitration eligible players and other players in their pre-arbitration years who are still under team control, the Yankees currently have a payroll of roughly $244 million.

Can the Yankees fit in a player like Bellinger, who is projected to make somewhere around $27 million per season, and still make other needed moves while staying under the $304 million luxury tax threshold?

If that is indeed the goal, while it does appear possible, there doesn’t seem to be a lot of wiggle room.