Yankees' Brian Cashman Could Break Character for Jazz Chisholm

The New York Yankees are entering an offseason full of question marks, and perhaps one of the more under-the-radar issues is what to do with All-Star second baseman Jazz Chisholm.

Chisholm is preparing to enter the final year of his contract and stands to reap a rather robust contract if he hits the free-agent market next offseason.

But will the Yankees let things get that far?

New York general manager Brian Cashman isn't typically in the business of handing out contract extensions. You rarely see it happen in the Bronx, and when the Yanks have done it (like with Luis Severino and Aaron Hicks), the deals didn't work out.

But could Cashman ultimately break character for Chisholm, who smashed 31 home runs while also stealing 31 bases this past season?

It's a question that Cashman will surely be asked at the GM meetings this week, and it's one that he will almost certainly not answer directly.

However, given the dearth of top-tier second baseman in today's game, it stands to reason that now might be as good of a time as ever for Cashman to subvert his policy on contract extensions.

Chisholm is 27 years old (he turns 28 in February) and seems to relish playing in the Bronx. He loves it, and he just enjoyed the best season of his career. In fact, since joining the Yankees through a trade deadline move with the Miami Marlins in 2024, Chisholm has registered an .816 OPS while also displaying tremendous improvement defensively.

There are definitely reasons to wonder whether or not the Yanks can trust Chisholm long term, however. The Nassau, Bahamas native has a rather checkered injury history, and he does have a reputation for being a bit of a hothead. Just ask umpires around baseball.

Plus, the Yankees are not nearly as spendthrift as they once were, and given that Chisholm could command a deal worth in the neighborhood of $200 million, it would not be the least bit surprising if Hal Steinbrenner balks.

We also have to consider that New York has top prospect George Lombard Jr. in it farm system, and if Anthony Volpe gets healthy and re-establishes himself as a key piece moving forward in 2026, the Yanks could have a Lombard-Volpe middle of the infield for the long haul.

I'm not sure how much the Yankees are banking on Volpe at this point, but it's something to consider, especially considering New York could then move Volpe over to second base to clear room for Lombard, who actually struggled in the minors offensively this past season.

But the Yanks are also a win-now organization, and there is no question that retaining Chisholm for at least the next couple of years gives them the best shot to win a World Series rather than hoping that Volpe recovers and that Lombard becomes a star by 2027.

Extending Chisholm is absolutely something that Cashman will have to consider in the coming weeks and months. Whether or not he actually strikes a deal with the slugger, though, is another story entirely.