
Heading into the offseason, there was considerable chatter about the New York Yankees handing second baseman Jazz Chisholm a contract extension. Brian Cashman even addressed it, saying it was something they could possibly look into.
But here we are with the Winter Meetings about to begin, and we have heard essentially nothing about the Yankees signing Chisholm to a long-term deal.
Perhaps New York is simply addressing bigger priorities first, but it's also worth noting that the Yankees don't typically give extensions.
Chisholm is slated to hit free agency after next season, so if the Bronx Bombers don't extend him, he could walk for nothing next winter. That is, of course, unless they trade him.
Yankees insider Bryan Hoch pitched the possibility of a Chisholm trade on SNY, and he mentioned one particular factor as a reason for a potential move.
"Is he a part of the Yankees for four to five years? Do they see his personality in the room for four to five years?" Hoch said.
Chisholm's personality strongly differs from clubhouse leaders Aaron Judge, Giancarlo Stanton and Gerrit Cole. While those three are very cool and collected, Chisholm is far more expressive and has been accused of being a bit of a hothead at times.

Just ask umpires around baseball how they feel about Chisholm's antics.
Remember: Chisholm also ran into problems in the Miami Marlins locker room before even arriving in the Bronx, although there are definitely two sides to that story, and it seemed that his issue was with Miguel Rojas more than anyone else.
Regardless, Chisholm does have a disposition that is considerably different from what you would expect from a Yankee, and you do have to wonder if he could ultimately rub some of his teammates the wrong way as time passes.
Hoch added that Chisholm is actually one of New York's top trade chips at the moment after slashing .242/.332/.481 with 31 home runs and 80 RBI over 531 plate appearances in 2025, also stealing 31 bases. Plus, he showed tremendous improvement defensively.
The 27-year-old could be in line to land a deal worth in the neighborhood of $200 million, and whether or not the rather stringent Hal Steinbrenner would want to dole out that much cash to a mercurial player with an extensive injury history is very questionable.
Chisholm owns a lifetime .770 OPS since breaking into the big leagues in 2020 and has made a pair of All-Star appearances.
The Yankees acquired him in a trade with the Marlins in July 2024.