Alexander Wilson
There is nobody in baseball quite like Jazz Chisholm, and that is equally a compliment and a warning for the New York Yankees.
The man spent spring training announcing he wants to become only the second player in baseball history to hit 50 home runs and steal 50 bases in the same season, called out the Dodgers in a quote that then mysteriously disappeared from the internet, and casually dropped that he is looking for $35 million per year over eight to ten years before he has thrown a single pitch in a game that counts. All of that happened before Opening Day.
“I think the contract year is even better for me,” Chisholm told reporters this spring. “I like pressure. It’s just like a roller coaster. If you don’t enjoy the ride, it’s gonna suck. When you enjoy the ride, it’s one of the best rides of your life.”
Buckle up.
What He Brings to the Table
The confidence is not detached from reality. In 2025, Chisholm posted a .242/.332/.481 slash line with 31 home runs, 31 stolen bases, 80 RBIs, and a 126 wRC+ across 130 games. He won a Silver Slugger. Made his second All-Star team. Became only the third Yankee in franchise history to post a 30-30 season, joining Bobby Bonds and Alfonso Soriano. His full statistical profile shows a hitter with genuine power, real speed, and the kind of plate discipline that makes those two tools even more dangerous.
The defense is legitimately underrated too. Chisholm’s range and athleticism at second base give the Yankees a middle infield anchor that most clubs cannot replicate. He brings an energy to the clubhouse that teammates genuinely feed off. When he is locked in and healthy, he is one of the most exciting players in the American League.
The operative words there are locked in and healthy. Chisholm has played more than 140 games exactly once in six major league seasons. His volatility, both offensively and in terms of availability, is part of the reason the Yanks have been slow to initiate extension talks.
The Money Gap Is Real
Here is where the math gets uncomfortable. Chisholm is earning $10.2 million this season after avoiding arbitration in January. He wants $35 million annually for nearly a decade. That gap is not a negotiating position. That is an entirely different conversation.
Cashman was direct about the organization’s approach at the Winter Meetings, per MLB.com. “We let these things play out, for better or worse,” the GM said. Translation: do not expect a deal until November. Maybe not even then.
There is a historical precedent that matters here. Gleyber Torres was productive for years at second base, and the Yankees still let him walk in free agency because they were not willing to meet his market price. Torres signed with Detroit for less than expected, but the organizational message was clear enough: Cashman does not overpay for the position. Chisholm is a better player than Torres was at his peak, but the principle does not change just because the player does.
“He’s a winning player. He brings a lot of energy and a lot of joy,” Cashman told reporters. High praise. Not a contract.
What Comes Next
Chisholm has said he does not want to leave New York. “I love it here. I can’t say I want to be anywhere else but here,” he told Jon Heyman of the New York Post. But love does not pay the bills, and if an offer does not come that meets his expectations, there will be teams with money ready to spend it in November.
The Yankees are not without options on the back end. George Lombard Jr. is climbing through the system quickly. If he has a big year in Triple-A in 2026, there is a plausible world where he takes over at shortstop in 2027 with Anthony Volpe sliding to second base. That is a long way from being a real plan, but it is why Cashman may feel less urgency than Chisholm wants him to.
I think the Yankees want to keep him. I also think they are not going to pay $35 million per year for a player who has topped 140 games once in his career. The season will determine a lot. If Chisholm stays healthy and puts up another 30-30 season, the negotiating leverage shifts meaningfully. If he chases the 50-50 and falls short but stays on the field, the argument is still strong.
His contract year starts Wednesday night in San Francisco. If the first half looks anything like last April, this conversation is going to get very loud very fast.
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