5 Jazz Chisholm Jr. trades that could get the Yankees over the World Series hump

The New York Yankees “have listened” to trade offers for All-Star second baseman Jazz Chisholm Jr., per ESPN’s Jeff Passan. The 27-year-old joined the 30-30 club last season and provided consistent results in the heart of New York’s lineup. That said, he’s also on an expiring contract.

The Yankees need to find creative ways to flesh out the lineup if Hal Steinbrenner and Brian Cashman refuse to splurge in free agency. Chisholm has his fans and his detractors, but he’s one of the most entertaining players in the sport. He hammers right-handed pitching and he’s a malleable defender — most comfortable at second base, but with experience at third base and centerfield. The Yankees can trade Chisholm for prospects and depth, or they can attempt to scale up to an even bigger star. Here’s how it might look.

Cincinnati Reds

The Cincinnati Reds are in the market for a bat to upgrade the middle of the lineup. Kyle Schwarber talks fell through, but the Reds reportedly put a five-year, $125 million offer on the table — a sign that this front office, with Terry Francona leading the clubhouse, might be willing to spend more than usual.

Does that mean Cincinnati will put real assets on the line for a rental? Maybe not. But Chisholm is only 27 and $25 million AAV — with a few more years tacked on — could be enough to keep the Reds competitive in future free agent negotiations.

Chisholm finished last season with an .813 OPS and 125 OPS+, tallying 31 home runs and 31 stolen bases. He’s a plus defender at second base, if occasionally lax in his fundamentals. Matt McLain put up huge numbers as a rookie in 2023 (.864 OPS and 16 home runs in 89 games), but he missed all of 2024 and struggled immensely in his return last season (.643 OPS). He’s only 26 and under club control through 2029, so the Yankees have ample time to get McLain back up to speed, literally and figuratively.

Toss in an MLB-ready, back-end starter type in Julian Aguiar, who made seven starts for Cincinnati in 2024, and the Yankees at least need to consider the upside.

Pittsburgh Pirates

Nick Yorke was once considered a top prospect in the Red Sox pipeline before being dealt to the Pittsburgh Pirates in the ill-fated Quinn Priester trade. Still 23, Yorke put up muted MLB numbers last season — .583 OPS in 69 at-bats — but he looked much better with Triple-A Indianapolis. The Pirates’ player development system, especially for hitters, is a real crapshoot. Yorke could benefit immensely from a change of scenery. Plus, he’s still pre-arbitration, so the window of control is vast.

The Yankees also address their flimsy rotation depth, as Gerrit Cole, Clarke Schmidt and Carlos Rodón will all begin 2026 on the IL. Hunter Barco, 24, is a southpaw with a legitimate three-pitch mix. He blends a sinking fastball with a nifty slider (his best pitch) and a recently adopted splitter. He made a couple appearances out of the Pirates’ bullpen last season and could transition back into a starting gig with the Yankees.

Thomas Harrington, 24, is a righty with a solid fastball and four viable off-speed offerings, headlined by a sweeper that melts out of the zone and generates healthy swing-and-miss results. He gave up 18 hits and seven walks in 8.2 innings with the Pirates last season, but there’s reason for long-term optimism — if not as a back-end starter, then as a middle reliever as his command improves.

The Pirates, meanwhile, recover from their Kyle Schwarber whiff by adding the impact bat their lineup so desperately needs. Rentals are especially dangerous in a market like Pittsburgh, but if the front office is finally committed to building a winner around Paul Skenes, it’s clear they can afford to extend Chisholm. Never say never.

Philadelphia Phillies

The Philadelphia Phillies can use Jazz Chisholm as a one-for-one upgrade over Bryson Stott at second base, or as a solution to their myriad outfield woes. Either way, the Phillies would benefit Chisholm’s blend of power, speed and defense. Another left-handed bat isn’t exactly the ideal sales pitch, but Stott is basically a platoon, so this is a meaningful short-term upgrade. Plus, the Phillies are on the short list of teams genuinely comfortable spending big in free agency — at least historically.

Stott is under club control through 2027 at arbitration rates. He struggles immensely in lefty-on-lefty matchups, but raked consistently against righties in 2025 — especially late in the season. He’s only 28, so there’s still room for growth, in theory. He’s also an exceptional defender and a heck of a base-runner, so he can boost his value in the ancillary categories. Jazz covers plenty of ground on defense, but Stott will commit fewer errors and generally solidify the right side of New York’s infield.

There’s a case to be made in favor of Alec Bohm as a platoon option next to Ryan McMahon at third base, but the Yankees probably prefer Stott’s contract and defense over Bohm on an expiring deal. The Yankees could also demand both Stott and Bohm, although that may limit the prospect capital coming back. Philadelphia needs to fill its infield and put nine MLB hitters in the lineup.

The Yankees also receive two more or less MLB-ready pitchers. Moisés Chace is only 22, but his fastball is a grade-A weapon and he mixes in enough off-speed schtuff to play up a level. Jean Cabrera, 24, packs mid-90s heat and a changeup that misses a ton of bats.

Arizona Diamondbacks

Let’s now travel into slightly more ambitious — if less realistic — territory. The Arizona Diamondbacks are clearly anxious to trade Ketel Marte after some awkward off-field issues popped up in 2025. Marte is under lock and key through 2031 at an extremely affordable rate. He’s 32, so back half of the contract ages is a fair point of concern, but the Yankees are no stranger to such investments. Marte is still paid well below today’s market price for a star of his caliber.

The Diamondbacks might be willing to roll the dice on Chisholm, even as a potential rental. This isn’t Arizona attempting to shed salary, at least on the surface. It’s a fundamental issue with Marte as a teammate. Jazz isn’t necessarily lauded for his leadership qualities, but he plays hard and puts up numbers. The D’Backs clearly want to contend next season.

Arizona also has the money to potentially extend Chisholm, for what it’s worth. Corbin Burnes received a healthy $30.8 million annually. Take Marte’s money off the books, and there’s wiggle room to contend for Chisholm on the open market.

The Yankees aren’t going to win the Marte bidding war with a one-for-one swap due to Chisholm’s contract limbo. Add in a couple soon-to-be MLB arms in Elmer Rodríguez, 22, and Ben Hess, 23, and Arizona’s interest is probably piqued. Rodríguez has durability concerns due to a slight frame, but his fastball touches the high-90s and he has a healthy four-pitch arsenal. Command is the swing factor. Hess is built like a tank with an incredible fastball-curveball combo.

Detroit Tigers

The Detroit Tigers aren’t keen on trading Tarik Skubal, but he’s on an expiring contract and their chances of retaining him long term are basically zilch. As such, a bidding war is expected. The Yankees have the prospects — and the financial firepower — to toss their hat in the ring. Of all the potential landing spots, the Bronx Bombers have a better chance than most of re-signing Skubal next winter.

Chisholm ought to catch Detroit’s eye. Yes, trading Skubal for another rental is risky, but it’s not like Chisholm is the only asset coming back to Detroit. If the Tigers can add the day-one impact bat their lineup so desperately needs, it should help them stay competitive in lieu of Skubal. Meanwhile, Spencer Jones, 24, put up a .933 OPS and 36 home runs in 116 Minor League games last season. He can serve as a second power surge for the Tigers, who can slide him into center or right field rather easily. Jones has mechanical concerns with his swing — he strikes out a lot — but the rocket-like exit velocities can help to assuage doubt. Jones should benefit from Detroit’s player development.

The Tigers also get a couple young arms. Rodríguez could occupy a back-end rotation spot as soon as next season and blossom into a potential ace within years. Luis Gil won AL Rookie of the Year in 2024, finishing with a 3.50 ERA and 171 strikeouts in 29 starts. He put up a 3.32 ERA in 11 starts for the Yankees last season, but struggled dramatically with command upon his return from a lat strain. The 27-year-old got tattooed in the postseason and has issues to work through, but he’s under club control through 2028 and boasts frontline stuff.

Detroit might prefer more (read: better) prospects over Chisholm, which is totally valid, but this trade gives the Tigers a compelling blend of immediate production and long-term equity. Plus, if Detroit has money to toss at Alex Bregman and other free agent infielders, re-signing Chisholm might not be a completely lost cause. It’s certainly more attainable than re-signing Skubal.