Jazz Chisholm Jr. just put humiliating capper on a contract year that will cost him millions

This spring, an argument could've been made that Jazz Chisholm Jr. was the best position player set to hit free agency in the winter. Sure, that said a lot about how lackluster the class was overall, but Chisholm, a second baseman who hit 31 home runs and stole 31 bases while playing strong defense in 2025, was sure to be worth a ton of money — assuming he had a good contract year.

Woof. Chisholm set lofty expectations entering the 2026 campaign, saying he was shooting for a 50-home-run and 50-stolen-base season. Instead, he had arguably the worst year of his career, and things are only getting worse for him in the postseason.

Brutal contract year has only gotten worse for Jazz Chisholm Jr. in the postseason

Chisholm didn't start the New York Yankees' postseason opener, but he had a decent first two games in October, going a combined 2-for-5 with two walks and three stolen bases. Whatever good vibes he generated from those contests went down the drain on Monday, though, in what could be a season-defining loss for the Yankees.

Not only did Chisholm, like many of his teammates not named Ben Rice, go 0-for-4 with a strikeout, but he had a miserable day in the field. In the first inning, Chisholm, for reasons only he can explain, attempted to turn an impossible double play — only to throw the ball halfway up the first-base line, leading to the first run of the game crossing the plate.

As if that weren't bad enough, in the bottom of the fifth inning, with three of the Yankees' infielders in trying to prevent the go-ahead run from scoring, Chisholm was instead playing back a few steps, allowing the slow-footed Jonathan Aranda to score on a softly hit ground ball. Those were two massive defensive miscues from the normally sure-handed Chisholm, allowing the Rays to score two runs in what wound up only a three-run defeat. Oh, and he made another very poor throw in this game and was lucky George Lombard Jr. bailed him out. Who knows what this game could've been had Chisholm not embarrassed himself in the field?

Embarrassing Jazz Chisholm Jr. season will cost him millions in free agency

It's one thing to be outspoken. I, for one, love it when players are confident and themselves. I loved watching Chisholm play last season. It's another, though, for a player to be outspoken and play poorly. Chisholm has gone from being a joy to watch to being a player Yankees fans want benched because of games like this one.

He went from being the most well-rounded second baseman in the sport to one who posted the lowest OPS+ (97) in a full season in his career. His defense hadn't regressed much, but this game surely was a bad look in that department, too.

I don't know what to make of Chisholm's upcoming free agency now. On one hand, he's still a supremely talented 28-year-old with as much upside as any second baseman in the game. He could very well have a huge 2027 campaign with a change of scenery. On the other hand, it's fair to wonder if he'll ever reach those 2025 heights again. It's also fair to wonder whether he's worth the long-term investment he coveted entering the year.

At this point, Chisholm is likely looking at either accepting a one-year deal and betting on himself or taking a shorter-term, multi-year deal at a very low AAV. Neither of these options seems appealing for a player who seemed likely to get a contract around the $200 million mark entering the season, but that's what bad contract years get you in this sport.

With the Yankees down 2-0 in this best-of-five series, scoring just two runs in those two games, Chisholm is running out of chances to show his worth. And given how poorly things went on Monday, that might be for the best before he loses himself even more money.

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