Sep 19, 2026 2:30 PM

The Yankees infielder hasn't played well, but history is on his side.

Make-or-break seasons in Major League Baseball are never easy for pending free agents, something New York Yankees second baseman Jazz Chisholm has found out the hard way this summer. 

Chisholm, who was expected to be one of the better players on the free-agent market this upcoming offseason, just didn't have the year that he was expected to, and there's no other way to put it. 

Chisholm had high hopes, and so did Yankees fans, with many thinking he could potentially have 40 home runs and 40 stolen bases. Chisholm, however, hasn't swung the bat at the level everybody hoped for. There have been reasons, including injuries, but ultimately, he just didn't play the type of baseball he was expected to.

However, as the Yankees enter the winter, there's a lot to consider. 

If New York really wants to get creative, it could look to bring Chisholm back at a reasonable price. There is a chance he could be interested in taking a deal where he has to prove some things, perhaps taking a one-year deal with an opt-out in the second year, or even accepting the qualifying offer, but that still remains to be seen. 

The Athletic's Yankees reporter, however, believes it wouldn't be surprising to see another team bet on his upside.

“What the Yankees decide to do at second base will be one of the most fascinating storylines of the offseason. I agree with you, Marco, that this season has likely cost Chisholm millions. He is nearing the end of his worst offensive season since 2021. He won’t reach the heights he set for himself entering 2026, but he still could achieve a 20-40 season (homers, steals). Few players have the talent to post those numbers. 

“Before this year, Chisholm posted back-to-back 4+ fWAR seasons. It would not be wrong for the Yankees, or another team, to bet on his upside. Chisholm still offers tremendous defense at second and excellent base running. If his bat gets back to being considerably above average, he profiles as one of the best second basemen in the sport,” Chris Kirschner of The Athletic wrote.

With Chisholm's ability to leave the yard and steal bases at a very high level when he's at the top of his game, as well as his above-average defense, there's no reason why a team shouldn't take a chance on him. 

That's part of why I think the Yankees could be impacted by his free-agent market in some way. I believe more teams will be interested than some think, which could raise questions about his future.

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