The Toughest Contract Decision Facing the Yankees This Winter

The New York Yankees have several major decisions to make this offseason, as the 2026 season looks like a changing of the guard.

The emergence of homegrown players like Ben Rice, Cam Schlittler, Spencer Jones, and George Lombard Jr. coincided with injuries or underperformance from the team's veterans. One veteran who failed to meet expectations was second baseman Jazz Chisholm Jr., who will be a free agent after the completion of the 2026 World Series.

Chisholm, 28, was coming off a 30-30 season in 2025 and boldly proclaimed he would join the 50-50 club in 2026. But instead, the middle infielder saw his home run tally dip to just 19 while slashing a mediocre .231/.312/.399 with a 98 wRC+, despite stealing a career-high 41 bases. Chisholm also faced persistent criticism for his attitude, as his play on the field didn't justify his confident demeanor.

With Chisholm hitting the open market, the Yankees look prepared to part ways, based on reports from Mark Feinsand of MLB.com. However, the Bronx Bombers are treating this like an easy decision when it's much more complicated.

The case for replacing Jazz Chisholm Jr.

On one hand, the Yankees have a lot of options to address second base if they let Chisholm walk, both on the open market and internally.

In free agency, second base has one of the better crops of position players, with Brandon Lowe and Luis Arraez notably available. The former is an established left-handed power threat coming off a 35-homer season, and his swing would ideally fit in Yankee Stadium.

The latter is a three-time batting champion who greatly excels at putting balls in play, something the current Yankee lineup desperately needs. Both Lowe and Arraez have also made tremendous improvements in the field after years of struggling defensively.

As for internal options, the Yankees acquired Luis Garcia Jr. at the trade deadline in August; Garcia is a former second baseman who moved to first. Although his defensive metrics at second in the past were extremely rough, Garcia looked great at first base. It wouldn't be surprising if New York gambles on moving him back to second. Then Ben Rice would move back to first base, and the DH spot would be reopened for either Aaron Judge or Giancarlo Stanton.

Finally, the Yankees can turn to Anthony Volpe and bank on his resurgence. Volpe learned second base during his stay in the minors (as well as a bit of third base) and looked comfortable there, while also showing signs of figuring things out at the plate. The sample sizes are too small to fully commit to Volpe as a starting option, but it's worth having him compete for the starting job.

The case for keeping Jazz Chisholm Jr.

However, even with the abundance of options, it can be argued that none are better than Chisholm when he's at his best. Over the past two seasons, only two second basemen (Brice Turang and Nico Hoerner) have accumulated a fWAR higher than Chisholm's 7.8 mark.

Chisholm's combination of speed, power, and defense is very rare and difficult to replace by anyone in baseball, let alone at a premium position up the middle. In 2026, he was still worth 3.5 fWAR because his defense and baserunning were so valuable.

Last year, when Chisholm went 30-30, only three second basemen (Hoerner, Ketel Marte, and Turang) provided a higher fWAR than Chisholm's 4.3. When everything is clicking, he's one of the best middle infielders in MLB.

Additionally, there's a clear fix to help Chisholm return to his 2025 form. In 2026, he swung at 29.1% of pitches outside the strike zone (O-Swing%) and 63.9% inside the strike zone (Z-Swing%). Compare that to 2025, when Chisholm's O-Swing rate was 26.5% and Z-Swing rate was 67.6%. He still drew 56 walks for a 10.5% walk rate, but that was also a downturn from 2025, when he walked at a 10.9% rate.

The Yankees have always looked for hitters with strong plate discipline. And even with his 2026 regression, Chisholm has taken more walks since joining the Yankees compared to his time with the Miami Marlins. If the Bronx Bombers can help him concentrate on chasing less, there's no reason to believe Chisholm can't return to his 2025 form, or surpass it to reach new heights.

What the Yankees should do

Although Chisholm looked primed to earn a lucrative deal in free agency, that should no longer be the case after his down year. That works greatly in the Yankees' favor.

Instead of letting him walk, the Yankees should offer Chisholm a short-term, high-AAV contract with an opt-out after the 2027 season, functioning as a "prove-it" deal for Chisholm to return to form.

These kinds of deals are common, with Pete Alonso serving as a good example in 2025. He accepted a platform deal with the Mets after a down 2024, responded with a monster season, and then got the deal he wanted the next winter.

Granted, Alonso left the Mets for the Orioles, but given how much the Yankees value Chisholm's position, they'd be highly incentivized to bring Chisholm back if he responds with a bounce-back campaign.

Alternatively, the Yankees can attach a qualifying offer to Chisholm, much like they did with Trent Grisham last winter. However, compared to Grisham, Chisholm is a far more proven talent with greater upside. If Chisholm declines the QO and leaves, then the Yankees get a compensatory draft pick for their trouble.

Both routes would be better for the Yankees than simply letting Chisholm walk for nothing. Even if banking on a return to form from Chisholm is risky, all their other options have risks attached. Lowe and Arraez are both older and were below-average defenders until this year; Garcia has proven to be a below-average defender at second and has regressed since arriving in the Bronx, and Volpe's sample size at second is too small, on top of him failing to prove himself offensively yet.

Upon the Yankees' elimination in the ALDS, Chisholm was open about his desire to return to the Bronx. While it's far from guaranteed that he'll stay if the Yankees still show interest in keeping him, it's clear Chisholm is dissatisfied with his 2026 season and motivated to prove himself to the Bronx Bombers.

Considering MLB's uncertain future for 2027 and the rumblings of a potential salary cap, the Yankees may not be able to offer anything to Chisholm right away. But the Yankees need to decide whether they want to re-sign him or not before the lockout begins. And right now, it makes more sense to give Chisholm one last chance.

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