With the New York Yankees preparing for the 2027 season after another disappointing postseason exit, losing to the Tampa Bay Rays in the ALDS, one aspect of the team from this past year that needs to be figured out is Jazz Chisholm Jr., who's a free agent. As rumors will surround the Yankees this offseason, there will also be speculation on the command Chisholm will have in the winter, as one insider cites a story involving Derek Jeter that will have people talking.

On the topic of Chisholm's outlook for the offseason, Jim Bowden would say on “Foul Territory” that he's a “complicated issue” regarding his antics off the diamond. He would cite a time when Chisholm parked in the spot that belonged to Jeter when he was a rookie with the Miami Marlins and the Yankees legend was a part-owner of the team.

“Chisholm's a more complicated issue,” Bowden said. “I don't even know what to do with him sometimes. Love the talent. Metrics like him defensively.”

“I remember when he went into Marlin's spring training as a rookie, and he parked in Derek Jeter's spot,” Bowden continued. “I said, ‘Why would you park in Derek Jeter's spot, the owner of the team?' And he said, ‘Oh, he's not going to be here today, I don't think.'”

Jazz Chisholm Jr. once parked in Derek Jeter's spot as a rookie with the Marlins, says @JimBowdenGM. pic.twitter.com/2m8W9iOqxm

— Foul Territory (@FoulTerritoryTV) October 31, 2026

Insider talks about Jazz Chisholm Jr's offseason after Yankees stint

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This past season with the Yankees was a relatively underwhelming one for Chisholm, hitting a .231 batting average with 19 home runs and 55 RBIs, though recording a career-high 41 stolen bases. Talking about his offseason outlook, Bowden would say that a “second division team” could offer him more money than a contending team.

“It's hard for a contending team to want to pay him long term unless he takes a short-term deal and try to prove it again. But I do think you're going to have second division teams that'll make a run at them, just because there's not a lot of guys that can hit 20 and steal 40,” Bowden said.

It remains to be seen where Chisholm ends up and what the Yankees do this winter.