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    Matthew Schmidt
    Sep 22, 2025, 21:54
    Updated at: Sep 22, 2025, 21:54

    The New York Yankees and Jazz Chisholm might ultimately not be on the same wavelength when it comes to a long-term contract.

    Jazz Chisholm recently made it clear that he wants to remain with the New York Yankees long term. The All-Star second baseman has just one year left on his contract, and he if does hit the free-agent market next offseason, he will surely be a hot commodity.

    The question is, will the Yankees actually want to extend him on the money he will likely be seeking?

    Chisholm can say he wants to remain in the Bronx all he wants, but when it comes time to put pen to paper, money talks. It seems hard to imagine the 27-year-old not chasing the biggest deal available to him, and New York may not have the capacity — or the desire — to offer it to him.

    New York Yankees second baseman Jazz Chisholm. Credit: Daniel Kucin Jr.-Imagn Images.

    We've discussed this ad nauseam: these aren't the Yankees of yesteryear. Hal Steinbrenner is a very different person from his father, who ruled with an iron fist. Hal is very cost conscious. He is very aware of the luxury tax threshold. While he wants to build a winner and has proven he will attempt to make the necessary moves to do so, he won't pull the trigger if it means bleeding cash.

    Chisholm is having the best season of his career. He is slashing .242/.332/.487 with 31 home runs and 79 RBI. He also became just the third player in Yankees history to put together a 30-30 campaign, joining Bobby Bonds and Alfonso Soriano. Plus, he has shown tremendous improvement defensively since arriving from Miami in a midseason trade last July.

    On top of that, Chisholm has an infectious personality that absolutely lends well to the fan base, meaning a whole lot of merchandise sales.

    Ergo, the Bahamian native is not going to come cheap. He knows it, and so do the Yankees. It could create a rather ugly situation between the two sides.

    How Chisholm performs in the playoffs this year may also play a significant role in how New York views him long term. He was all but invisible last October, and he owns a lifetime .167/.236/.288 slash line over 17 playoff games between the Marlins and the Yanks.

    New York Yankees second baseman Jazz Chisholm. Credit: Eric Canha-Imagn Images.

    Small sample size? Sure, but don't think for a second New York won't take his postseason numbers into account when it comes to negotiating a new deal. That matters above all else in the Bronx, and it's why Aaron Judge is not yet truly in the same class as the Babe Ruths, Mickey Mantles and Derek Jeters of the world. At least in Yankee lore.

    Steinbrenner and Co. will have the opportunity to sit down and hammer out an extension with Chisholm this winter in order to get out ahead of things, but it's entirely possible that the infielder could command $200 million or more depending on the length of the contract.

    Whether or not the Yankees would be willing to pay that price remains to be seen. If Chisholm has a strong postseason showing, it could influence New York to just give him what he wants. If not? The Yanks may allow him to test the open market, and the fact that Chisholm also has a checkered injury history could make New York perfectly comfortable with doing just that.