Yankees Should Give Free Agent Reliever Another Shot

Devin Williams was part of a trio of New York Yankees who attended a Knicks game at the end of October. He and Cam Schlittler sat with the captain, Aaron Judge, replacing Judge's old Gardenmates of past years, DJ LeMahieu and Anthony Rizzo.

This may have just been an outing among teammates, but Williams is a free agent this winter. If one puts on their conspiratorial hat, they could almost see a situation where Judge is effectively courting his former teammate, showing him a night on the town in hopes he gives New York one more shot.

New York Yankees pitchers Devin Williams and Cam Schlittler — Oct 22, 2025; New York, New York, USA; New York Yankees pitchers Devin Williams (left) and Cam Schlittler pose for a photo court side before an opening night game between the New York Knicks and Cleveland Cavaliers at Madison Square Garden. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images

A Turnaround for Devin Williams

That might be looking into it too much, and it is a touch of fan fiction, but the end of Williams' season was much more promising than how it started. Heading into September, Williams had a 4.99 ERA in 52.1 innings. The month then started as poorly as the rest of his season had, with a meltdown in Houston against the Astros, where he was thrown out of the game.

At his lowest, when the noise over Williams' place on the team was loudest, he finally did turn that proverbial corner that manager Aaron Boone likes to mention. The former all-star followed that Houston debacle with nine scoreless innings in September. He struck out 12 and walked two.

Williams' postseason was just as good. He didn't allow a run in the 4 IP. He struck out four and allowed two walks.

When asked if he would return to New York after his season ended, Gary Phillips of the Daily News reported that the reliever was open to it. He told Phillips he has "grown to love being here. I love the city. I love taking the train to the field every day. I really enjoyed my experience."

What Williams May Earn in Free Agency

As for what Williams has the potential to earn on the open market, Baseball America predicts he'll secure a four-year deal worth $75 million. It's around what they believe other free agent relievers, such as Ranger Suarez, and the other struggling New York reliever, Ryan Helsley, may get.

Oct 1, 2025; Bronx, New York, USA; New York Yankees relief pitcher Devin Williams (38) reacts during the eighth inning of game two of the Wildcard round of the 2025 MLB playoffs against the Boston Red Sox at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images

Whether it's a good process to pay that for a reliever who struggled for most of the year is one question the organization would have to ask itself. Their luck ran out in terms of finding diamonds in the rough for the bullpen and converting them into outs machines. This season, the Yankee pen had a 4.37 ERA. It was the 8th worst in the league. Every team worse than them all missed the postseason. The bullpen became a situation of getting what you pay for.

Splurging on Williams or spending more than they have in the past for relief help is something the Yankees could have to resort to. There's a good chance they'll balk at that $75 million price tag, but if it's more to their liking and both parties can meet in the middle, a reunion should be something the Yankees consider.

Williams admitted that the move from Milwaukee to New York contributed to his struggles. Having acclimated to this environment, spending nights out with Judge might be a recipe for a better sophomore season.

If Williams ends up pitching up to his potential over the course of a full season in year two, he would be the type of stability the Yankees searched for all year.

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