The Yankees team won the World Series in 2009, and since then, they have been just waiting for their next winning title. To win that title back in 2026, Brian Cashman will need to work on their roster and fill all the gaps by making vital decisions, and one of such decisions could be not re-signing the veterans, Devin Williams and Luke Weaver.

Insider Jim Bowden reported, “The Yankees acquired Williams last winter with hopes he’d be the impact closer he was with the Brewers. Unfortunately, that’s not what they got as he ended the season with an ERA near 5.00 and a negative bWAR. He did finish strong, however, pitching well in September and during the postseason. His Bugs Bunny changeup was there at season’s end, too, and it provides hope that he could rebound with a different team next year”.

Williams played in the majors with the Brewers from 2019 to 2024 before being traded to the Yankees, and no one can ignore Williams’ dominance on the field in that timeframe. For instance, he was named the NL Reliever of the Month for September 2020. The veteran also surrendered just four hits with no runs and recorded 24 strikeouts in 13 innings.

His dominance did not stop there. In 2023. Devin Williams had a 1.53 ERA with 36 saves. That season, he won the NL Reliever of the Year award for the second time. Then came 2024, and in March of that year, it was announced that he would miss three months because of two stress fractures in his back. However, that feature also did not stop him from showing his power. After returning to the team on July 28, Williams logged a 1.25 ERA with 38 strikeouts in 22 appearances.

However, that dominance was not seen in 2025. Like Jim Bowden, MLB.com’s Bryan Hoch also pointed out Williams’ rollercoaster season with the Yankees. After Game 3 of ALDS, where Williams got a standing ovation from the crowd, Hoch said, “His performance included four outs in that ALDS Game 3 against the Blue Jays, the only time all year he pitched more than an inning, producing a crowd reaction that Williams said, “was definitely better than what I heard for much of the year.”

Now, if we go back to Jim Bowden’s prediction, then we can see that Luke Weaver’s future with the team is also uncertain. Bowden reported, “Weaver was one of the best high-leverage relievers in 2024 for the Yankees, and he had a dominant first half of the season this year, posting a 2.91 ERA”.

Last year, till September, Weaver finished the season 4-for-4 in save chances, containing a five-out performance, and that performance sealed a 7-4 victory over the Athletics on Sept. 22. Over the final 8 appearances before October, 2024, the star limited the team’s rivals to one unearned run and 4 hits across 11 innings. He also walked three while striking out 24.

Now, if we focus on 2025’s first half, then we can see on May 25, he secured a 5-4 Yankees victory against the Rockies by closing out the game in the bottom of the 9th inning. On May 14, the veteran again sealed a 3-2 Yankees win against the Mariners by earning a save.

But, in the 2nd half, the situation shifted where the star posted a 4.40 ERA, and “this winter, teams will have to decide whether Weaver’s second-half issues are fixable and he can be the pitcher he was in the first half”, Jim Bowden said.

So, where can the 2 veterans go if Brian Cashman releases them? As per Bowden, for Williams, the most suitable team would be “Brewers, Braves, Reds, Tigers, Rangers, Giants,” and for Weaver, the options will be “Braves, Cardinals, Giants, Athletics, Angels, Orioles”.

While the future of Williams and Weaver is uncertain, Cashman’s rebuilding strategy could not stop there. Meanwhile, rumors surrounding another Yankees star’s future in New York are catching a lot of traction. 

Jazz Chisholm Jr. could face an uncertain future amid infieldthe  overhaul

Jazz Chisholm Jr. is going to be 28 in February 2026 and is predicted to make 10.2 million in the final year of arbitration, according to MLB Trade Rumors. The star will also enter free agency after 2026. Analyzing this situation, SNY’s Anthony McCarron reported. “The Yankees could seek to sign him to an extension or move him as part of an infield restructuring if they don’t envision him as a long-term Yankee. The problem with trading him is this: Chisholm provides up-the-middle athleticism, speed, and power. He was only the third Yankee ever to have a 30-30 season, joining Alfonso Soriano and Bobby Bonds. And he brings much-needed élan to a franchise that can profile as staid.”

Still, separating from Jazz Chisholm Jr. could come with a high price. The 28-year-old shone in his first full season in pinstripes, posting a .242/.332/.481 slash line with 31 homers and 31 steals, adding to the names such as Alfonso Soriano and Bobby Bonds, because they are the only Yankees to achieve a 30-30 campaign. He also counted among MLB’s top second basemen with 4.4 fWAR and elite defense.

As per Greg Joyce of the New York Post, the discussion regarding the extension has yet to start, but both sides look optimistic about the future. Unless Casman adds several infielders this winter, it is unlikely the Yankees will pull the trigger, though the mere discussion underlines how bold this offseason could become in the Bronx.

The Yankees’ offseason run is at a junction, with Brian Cashman counting loyalty against long-term vision. Exit of the trusted veterans and trade possibilities, such as  Jazz Chisholm Jr., point to the potential culture shift. One thing is obvious: New York’s 2026 fate depends on Cashman’s postseason strategies.