​NEW YORK, NEW YORK – APRIL 15: Jazz Chisholm Jr. #13 of the New York Yankees looks on during the ninth inning of the game against the Los Angeles Angels at Yankee Stadium on April 15, 2026 in New York City. All players are wearing the number 42 in honor of Jackie Robinson Day. (Photo by Dustin Satloff/Getty Images)Getty ImagesThe New York Yankees are heading into the final weeks of the season with an increasingly important question surrounding star infielder Jazz Chisholm Jr.:The 28-year-old second baseman is headed toward free agency at the end of the season, with some prolonged collective bargaining agreement negotiations ahead and a poor season following him.Chisholm entered 2026 coming off the best offensive campaigns of his career, when he hit 31 home runs with an .813 OPS while stealing 31 bases for the Yankees. This year, though, his production has declined, potentially changing the kind of contract he can command this winter.“Chisholm’s down season has also hurt his value in free agency,” Chris Kirschner concluded for The Athletic. “He knows what’s at stake this offseason, but he said it hasn’t gotten in his head.”FORBES | By Peter ChawagaMember Of Yankees’ Legendary World Series Championship Roster DiesNew York Yankees’ Jazz Chisholm Reveals Brian Cashman’s Extension StanceChisholm recently confirmed that he and the Yankees have not discussed his contract situation since spring training and he made it sound as if an extension had already been outright rejected.“It was just like, ‘We don’t do extensions,’” Chisholm said of the talks, according to NJ.com’s Randy Miller. Chisholm described the update as an informal interaction with Yankees general manager Brian Cashman, who has famously avoided extending players before they reach free agency during his tenure.“I would not say I reached out,” Chisholm added, per Miller. “It was more of a mutual thing. It was me walking around saying something to Cash. He walked past me.”That leaves Chisholm heading toward the open market, though his 2026 season makes the situation complicated.Chisholm has 19 home runs and 40 stolen bases, but his .229 batting average and .713 OPS are both down from last year’s .242 average and .813 OPS. He is still producing power and speed at a level few second basemen can match, but the overall offensive decline could make a massive contract more difficult to secure.FORBES | By Peter ChawagaDodgers’ Pending $400 Million Free Agent Could ‘Gravitate’ Toward Angels ContractNew York Yankees’ Jazz Chisholm Praises Philadelphia Phillies Ahead Of Free AgencyOne potential landing spot seems to be the Philadelphia Phillies, and Chisholm himself acknowledged the appeal of what the club has built.“Me and (Phillies manager Don Mattingly) are like this,” Chisholm said while indicating closeness with his fingers, according to Miller. “Me and his son, his wife … all of us are tight. I love Don Mattingly. The Phillies got (Kyle) Sc