Latest rumor has Yankees putting themselves in poor position for 2027 season

Jazz Chisholm Jr. feels like a perfect fit with the New York Yankees, but his future with the club remains shrouded in doubt. Chisholm is entering a contract year in 2026, but there are question marks beyond that, as the Yankees haven’t gotten an extension done with their mercurial slugger. What’s more, a new report from The New York Post’s Greg Joyce indicates that an extension for Chisholm probably won’t happen before the start of the 2026 season.

“Delivered a 30-30 season despite missing a month because of an oblique injury,” Joyce wrote of Chisholm. “Entering his walk year, he wants to stay long-term, though an extension is unlikely before the season starts.”

Failing to extend Jazz Chisholm Jr. would be a mistake by the Yankees

With a looming lockout headed for MLB in December 2026, failing to lock in Chisholm long-term before the league's contract landscape possibly changes (and potentially becomes less flexible) would be a mistake by Yankees GM Brian Cashman. 

Despite Jazz’s flaws as a player, he’s undeniably one of the best second basemen in the game. Furthermore, his swing suits Yankee Stadium, his personality suits New York, he has expressed a desire to remain with the Yankees, and he’s in the midst of his prime. What more does Cashman need to be convinced that Chisholm should be a long-term priority for the Yanks?

Trading him certainly doesn’t make sense, as it would be tough to replace his production at the position. 

Chisholm, still just 27, hit .242/ .332/ .481/ .813 in 2025 with 31 home runs and 31 stolen bases in 130 games played, picking up his second All-Star selection along the way and finishing the year with a Silver Slugger finalist nod. He’s the third player in the Yankees’ storied history to have a 30-30 season.

He was good last year, too, after coming over from the Miami Marlins in a midseason trade, hitting .273/ .325/ .500/ .825 with 11 homers and 18 stolen bases in 46 games.

Though he’s error-prone defensively, Chisholm does have excellent range at second base and often turns would-be hits into outs. He finished 2025 with two Defensive Runs Saved and eight Outs Above Average.

At the end of the day, Chisholm is a star, and even a fringe superstar if he continues trending upward as he approaches his thirties. He’s done nothing on the diamond to suggest that the Yankees shouldn’t invest in him long-term, and yet for some reason, an extension before the upcoming campaign is reportedly unlikely.

If that reporting holds, Chisholm may soon be added to a growing list of offseason whiffs in recent years by the Yanks.