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Michael DeRosa

By Michael DeRosa

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The New York Yankees have multiple pending free agents heading into the offseason, but Jazz Chisholm Jr is the most notable.

Chisholm is coming off a down season with the Yankees, as he posted 19 home runs, 55 RBI, and a .231 batting average in 137 games. However, he also had 31 home runs, 31 stolen bases, and 80 RBI during the 2025 season as an All-Star in New York. Thus, he should generate a good amount of interest in free agency if he tests the market.

Now, the Yankees are being predicted to lose Chisholm to a very surprising team.

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Jazz Chisholm Jr.

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In a recent article for Bleacher Report, Kerry Miller predicted that the Pittsburgh Pirates will sign Chisholm in free agency this offseason.

With the Pirates not being known for being big spenders, it would be a big surprise if they landed Chisholm. Yet, with the Pirates being on the rise and looking to become true contenders with Paul Skenes as their ace, it would make sense if they tried to sign a star talent like Chisholm.

If the Pirates signed Chisholm, he would provide them with another impactful hitter for the front half of their batting order. This would especially be the case if he regained his 2025 form as a member of the Pirates.

Nevertheless, it will be interesting to see if the Pirates can end up landing Chisholm in free agency. If they are unable to re-sign fellow second baseman Brandon Lowe, Chisholm would be a very good player to replace him with.

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