We all know that the New York Yankees have one of the most talented squads with players like Aaron Judge and Jazz Chisholm Jr. And with Jazz Chisholm Jr dropping a 30/30 season in 2025, he has some demands that the Yankees need to meet if they want to keep him beyond 2026.

And his demands, like his lifestyle, are living large. Because Chisholm Jr wants a $350 million contract.

In a recent interview, Jazz Chisholm Jr said, “It’s probably bigger than that now, probably $35 million… I’d say no because I know I can get $35 million somewhere else. That’s $10 million less a year… I’m 28. I want 8 to 10 years.”

Jazz Chisholm Jr has made contract expectations clear entering his final Yankees season today.

He told NJ.com he wants a $35 million annually across eight-to-ten years. That demand equals roughly $280 million to $350 million total guaranteed contract.

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Yankees general manager Brian Cashman now faces enormous financial pressure in handling upcoming negotiations. Fans already sense tension building between confident player demands and cautious front office leadership.

That confidence comes after his remarkable 2025 season with powerful two-way production numbers.

He smashed 31 home runs and stole 31 bases across 130 games, pushing him into the 30-30 club. His .813 OPS matched elite hitters and earned him a deserved Silver Slugger recognition award. He earned an All-Star selection while producing 4.2 WAR across a demanding regular season. Only three New York Yankees players ever achieved 30-30 seasons before Chisholm Jr.

Yet comparing salaries shows how steep his requested annual salary truly is.

Cody Bellinger, who the Yankees re-signed recently for a $32.5 million AAV, produced stronger value while earning a similar salary to what Jazz Chisholm Jr expects.

Bellinger posted a .272 average, 29 homers, and a superior 5.1 WAR, while also showing an 11 defensive runs saved. Chisholm hit a .242 average with a -2 defensive runs saved and a higher total of errors recorded.

Those comparisons complicate negotiations and influence how the Yankees evaluate massive financial commitments moving forward.

Financial caution from ownership also shapes expectations surrounding any potential record-breaking agreements.

Owner Hal Steinbrenner previously emphasized balanced payroll and avoiding reckless spending. Recent winters saw the Yankees avoid contracts exceeding $300 million despite available marquee stars like Edwin Diaz and Kyle Tucker.

That spending pattern creates uncertainty around meeting Chisholm’s extremely ambitious financial expectations. Cashman must balance rewarding production while protecting long-term roster flexibility moving forward.

Meanwhile, ongoing silence between both sides hints negotiations could remain unresolved entering the season opener.

Chisholm already rejected a hypothetical $25 million offer, insisting he deserves significantly more annually. Free agency looms after 2026, increasing pressure with every passing day.

Fans watch closely, knowing elite performance might determine whether extension becomes reality. If positions remain firm, 2026 could mark an emotional farewell between player and franchise faithful.

Jazz Chisholm Jr makes it clear which team he won’t join if he can’t reach a deal with the Yankees

Jazz Chisholm Jr wants a $350 million contract, but the New York Yankees will be thinking a million times before even getting close to that number. And if they don’t, Chisholm Jr says he will find a new home. But he says it will never be the Los Angeles Dodgers.

Jazz Chisholm Jr. made it very clear where his heart and head are as he enters free agency, saying, “I’d go to the Angels before I’d go to the Dodgers, because I’d want to go and win by myself and build my roof” rather than join that club.

This isn’t just idle talk; the Los Angeles Dodgers and New York Yankees have one of baseball’s oldest World Series rivalries, meeting a total of 12 times for Fall Classic titles, and the Dodgers beat the Yankees 4–1 in their most recent matchup.

Chisholm’s refusal carries extra meaning given how tough and emotional that 2024 Series felt for Yankees fans who saw their team’s big early leads slip away.

At the same time, Chisholm isn’t shy about putting a charge into the narrative around elite players like Shohei Ohtani, telling reporters in Tampa that “you’re looking at the second one” when reminded that only Ohtani has ever hit 50 homers and stolen 50 bases in a season.

That 50–50 leap is among baseball’s rarest achievements, made once by Ohtani in 2024, and Chisholm is embracing that challenge loudly as he prepares for 2026. His words mix confidence with a sense of urgency that comes from playing in a big stadium where fans live every at‑bat like a moment in history.

Taken together, those two stances say a lot about the man Chisholm wants to be remembered as. He makes it clear money alone won’t lure him to the rival Dodgers, choosing his own path over the easy route, a stance born from years in baseball’s fiercest postseason matchups.

And by publicly eyeing a 50–50 season, he’s signaling that he doesn’t just want to succeed in the lines on the stat sheet, he wants to match the game’s greats and craft a legacy that feels earned.