The New York Yankees are no strangers to giving star players big contracts. In fact, the Bronx Bombers are expected to have a projected payroll of around $300 million for the 2026 season. This particular figure would be the third-highest total of all Major League Baseball teams. Luxury taxes would push the amount even higher.
Despite the eye-watering financial report, the Yankees will have to figure out a way to keep one of the best players beyond the upcoming campaign. Jazz Chisholm is set to become a free agent following the 2026 season. The two-time All-Star recently avoided arbitration by agreeing to a one-year, $10.2 million deal. Nevertheless, the infielder is widely expected to receive a substantial raise in his next contract.
While exact figures regarding the upcoming long-term deal are not yet known, The Athletic’s Jim Bowden is making a bold prediction. The former Washington Nationals general manager expects New York to re-sign Chisholm to a massive contract extension.
“Jazz Chisholm Jr. signs a 10-year, $300 million deal to remain with the Yankees,” Bowden writes in a series of predictions for the outlet. “This comes on the heels of Chisholm’s second straight 30/30 season.”
As Bowden points out, Chisholm is coming off his best season as a professional. Along with hitting 30 home runs and collecting 30 stolen bases, the infielder posted an impressive 4.2 WAR and .813 OPS. His efforts were rewarded with an All-Star game appearance and the Silver Slugger award. Assuming he maintains these statistics in 2026, he will earn a massive pay raise.
Jazz Chisholm May Join New York Yankees Duo in $300 Million Club
GettyJazz Chisholm is expected to be a key player for the Yankees in 2026 and beyond.
Although Chisholm will almost certainly receive a significant long-term contract, Bowden’s prediction is certainly bold. According to Baseball Reference, only 15 MLB players have ever received $300 million deals. New York previously gave both Aaron Judge and Gerrit Cole contracts surpassing this figure.
Perhaps the best comparison regarding the situation would be Trea Turner’s 11-year, $300 million deal with the Philadelphia Phillies. The fellow infielder earned the contract at the age of 29 after posting a 5.2 WAR and .809 OPS with the Los Angeles Dodgers in 2022. Chisholm is currently 28, but will be 29 at the start of the 2027 season.
Back in January, it was reported that Chisholm could be looking for an extension in the seven-year, $180 million range. If so, this would put the Yankees star in a similar position as Willy Adames. The infielder previously signed a seven-year, $182 million deal with the San Francisco Giants before the 2025 campaign.
Star Slugger Wants to Stay in New York
Ultimately, Chisholm’s future contract will depend largely on how he performs in 2026. Either way, the second baseman would clearly prefer to remain in the Bronx. In fact, he recently proclaimed that he does not even think about free agency. “Everybody knows I love New York, and I want to be in New York, so being a free agent isn’t really on my mind as much as anything,” Chisholm told YES Network’s Meredith Marakovits.
Chisholm and the Yankees opened their 2026 campaign with a win against the Giants on March 25. The second baseman recorded one hit, as well as a stolen base, in three at-bats on the night. With mostly the same lineup, New York is expected to compete for the American League pennant once again this season.
Yankees Predicted to Give Star $300 million Contract Extension