NEW YORK — Brian Cashman just dropped a phrase that should make every Yankees fan sit up and pay attention. The general manager is exploring something he calls a “challenge trade.” And Jazz Chisholm’s name keeps coming up in the conversation.
The Yankees are not actively shopping their All-Star second baseman. Let that sink in first. But they are listening. In baseball front offices, that distinction can mean everything or nothing at all.
Multiple teams have called about Chisholm in recent days. The Yankees have picked up the phone each time. What happens next could reshape how the franchise approaches roster construction for years to come.
Cashman introduces unfamiliar concept
The term “challenge trade” might sound like corporate jargon. It is not. Cashman explained the concept during the Winter Meetings and again this week.
“We have really good players on this roster, and we are covered in most areas that you need to be covered,” Cashman told Chris Kirschner of The Athletic. “Then you peel the onion a little bit. So I think those players, individually, are all part of the solution rather than a problem. But I would call that a challenge trade. So we are open-minded to challenge trades on a lot of our talented players because, yes, we are left-handed. That is a problem. Is it a problem that can be solved in the near term, or does it have to try to get solved over time?”
Translation: The Yankees would swap major league talent for major league talent. Think the Brandon Nimmo trade to Texas for Marcus Semien. That kind of move.
Chisholm fits that mold. He just completed a 30-30 season while missing an entire month with an oblique strain. The 27-year-old slashed .242/.332/.481 in 130 games. He earned his first Silver Slugger award and represented the Yankees at the All-Star Game.
Those are not the numbers of a player teams typically shop.
Yankees face unusual roster problem
The issue is not Chisholm’s performance. It is his handedness.
Austin Wells, Ben Rice, Ryan McMahon, Trent Grisham and Chisholm all bat left-handed. That is five potential starters swinging from the same side of the plate.
“I acknowledge that we are left-handed dominant throughout our lineup,” Cashman said during the Winter Meetings. “So to get more choices for our manager would be a great thing for us to do.”
The Yankees led Major League Baseball in runs scored with 849 last season. They also led the league in home runs with 274. But October exposed the flaw. When opponents brought in left-handed relievers, the Yankees lineup looked vulnerable.
“I definitely want to give Aaron Boone some legitimate choices so he can match up when we’re facing a left-handed starter, because obviously we’re so left-handed that it’s a vulnerability right now,” Cashman said.
Chisholm’s value makes decision complicated
The numbers tell a story of a player entering his prime.
Chisholm put up 4.4 wins above replacement in 2025. He hit 31 home runs and stole 31 bases despite missing 29 games. Only Bobby Bonds in 1975 and Alfonso Soriano in 2002 and 2003 had previously accomplished the 30-30 feat in Yankees history.
“He’s somebody who I think is currently part of the solution,” Cashman said recently. “Someone who has made us better by getting him two Trade Deadlines ago and giving us athleticism. He’s above average. He’s an All-Star second baseman; great defense, steals bags, power, all that stuff. He’s been a good get.”
Chisholm is projected to earn $10.2 million in arbitration for 2026. He becomes a free agent after next season. The Yankees have not signed an extension with a player in six years. If they know Chisholm will walk after 2026, trading him now for longer-term assets makes strategic sense.
Several teams already checking in
The Pirates, Mariners, Guardians, Astros and Giants have all been connected to the second base trade market. Multiple reports confirm the Yankees have received calls about Chisholm specifically.
ESPN’s Jeff Passan and MLB.com’s Bryan Hoch both reported the interest. Neither suggested the Yankees are actively pushing him out the door.
The second base market is crowded this winter. Ketel Marte in Arizona, Brendan Donovan in St. Louis and Brandon Lowe in Tampa Bay are all theoretical options. That competition could dilute what teams offer for Chisholm. Or it could work in the Yankees’ favor if other deals fall through.
What would Yankees need in return?
Cashman has made clear the Yankees need pitching. Gerrit Cole is tracking toward a late May or June return from Tommy John surgery. Carlos Rodon underwent elbow surgery in October and projects to return in April or May.
A starting pitcher with multiple years of control would be the ideal return. The Yankees could also trade Chisholm for pitching, then sign a free agent to replace him at second base. Bo Bichette remains available on the open market.
That kind of creativity is exactly what Cashman means when he talks about challenge trades.
Decision may not come quickly
The Yankees re-signed utility man Amed Rosario to a one-year, $2.5 million deal on Saturday. The right-handed hitter gives Boone a platoon option against left-handed pitching. It does not solve the larger roster construction issue.
Chisholm has said publicly he wants to stay in the Bronx beyond 2026. Cashman has acknowledged the Yankees are willing to have “a legitimate conversation about value.”
For now, the phone keeps ringing. Cashman keeps answering. And Jazz Chisholm remains a Yankee whose future suddenly feels less certain than his 30-30 season suggested.
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