In July 2024, the New York Yankees swung a trade to acquire second baseman Jazz Chisholm in a deal with the Miami Marlins. Chisholm immediately looked rejuvenated in the Bronx, slashing .273/.325/.500 over 191 plate appearances. He then smashed 31 home runs while stealing 31 bases in 2025, earning himself an All-Star selection.

The problem is that Chisholm is preparing to enter the final year of his contract, and if he has another season similar to the one he just had in 2025, he is going to get paid next winter.

Advertisement

So, could the Yankees actually get out in front of it and hand Chisholm a contract extension this offseason?

MLB insider Robert Murray has provided an update on the situation, and while he isn’t ready to rule out a fresh deal for the 27-year-old, he seems to believe that Chisholm will ultimately hit free agency after 2026.

“His value entering the final season of his contract is enormous, and it would take quite an offer to entice him to forego free agency,” Murray wrote. “My best guess is that he plays out the year on his current deal and enters the market after the 2026 season.”

It’s also important to remember that the Yankees typically do not extend players. They did it with Aaron Hicks and Luis Severino, and they were burned on both occasions. They didn’t even extend Aaron Judge before he hit the open market after 2022, although they did try.

Advertisement

Plus, for as well as Chisholm played in 2025, he is a risky bet. The Bahamas native has a very checkered injury history, and while he seems well-liked in the Yankees clubhouse, he has definitely showed the propensity for being a bit of a hothead on the diamond. Just ask umpires around baseball.

Chisholm’s streakiness is also a big issue, and it’s worth noting that he is a lifetime .173/.247/.295 hitter in the playoffs across 98 postseason plate appearances. Definitely a pretty small sample size, but it’s still not what you want to see from a guy who is supposed to be one of your best sluggers.

Given how rare it is for second baseman — or middle infielders in general — to hit 30 home runs, Chisholm’s value is surely sky high right now, and I’m not entirely sure general manage Brian Cashman would be so willing to oblige.

Cashman did recently say that he wouldn’t dismiss the idea of an extension but that he had not yet spoken to Chisholm about a long-term deal.