Jazz Chisholm Is Giving The Yankees More Reasons To Let Him Walk In Free Agency

In his early days with the Miami Marlins, Jazz Chisholm Jr made his fiery personality known and was always in the headlines. One of the big reasons the New York Yankees could be shopping the star second baseman is how he handled being benched in Game 1 of the Wild Card series against the Boston Red Sox. 

Chisholm Is Going At It On Social Media

Jazz Chisholm Jr. proposed to his girlfriend, singer Ahnalys Santiago, on Christmas Day with a surprise under the Northern Lights during their vacation in Finland. After sharing the joyful news on social media, Chisholm faced a wave of inappropriate comments, something he addressed on Twitter, just as he did throughout the regular season. True to form, Jazz never hesitates to express himself and let his personality shine.

Brian Cashman and the New York Yankees are known for avoiding bad publicity and unnecessary headlines, which is an area where Chisholm often finds himself at odds with the organization. One notable instance occurred after the Game 1 Wild Card loss, when Chisholm, visibly frustrated about not starting against Garrett Crochet, avoided reporters by rummaging through his locker instead of addressing the media maturely and setting an example for his teammates.

Chisholm has also allowed frustration to affect his performance during games, engaging in disputes with umpires, and at times putting personal emotions ahead of the team. Regardless of his on-field production next season, these concerns contribute to the Yankees’ reluctance to offer him a long-term extension. Additionally, his ongoing durability issues, highlighted by significant time missed last season due to an oblique injury, further complicate his future with the team.

Will The Yankees Trade Jazz?

Reports have surfaced that the Yankees were open to offers for Jazz Chisholm, though a trade remains highly improbable. As one of New York’s most productive hitters, it’s unlikely the team could maximize his value with just one year left on his contract. Chisholm’s revamped approach significantly improved his performance. However, his postseason struggles ultimately overshadowed much of his regular-season success.

Acquiring Chisholm at the Trade Deadline stands out as one of Brian Cashman’s most astute moves as Yankees GM, but a long-term extension appears unlikely regardless of the team’s 2026 outcome. The Yankees are notoriously selective about awarding large contracts, and there are too many concerns about locking him in for the long term.

Final Thoughts

Brian Cashman is known for his thorough evaluation of both free agents and current players in pursuit of roster improvements. Retaining Jazz Chisholm is the most prudent decision as the Yankees gear up for another run at their first World Series title since 2009, competing in a stacked division with the Toronto Blue Jays, Baltimore Orioles, Boston Red Sox, and Tampa Bay Rays.