Not only has Jazz Chisholm Jr. been everything that the New York Yankees hoped for, but he’s quickly setting himself up to cash in when the time comes.
Whether or not that time could be within the coming months remains to be seen. For now, Chisholm continued his stellar 2025 with two more home runs and a stolen base in Tuesday’s 7-1 victory over the rival Houston Astros, pushing his respective season totals to 28 and 24. Barring injury, Chisholm remains well on pace to join Bobby Bonds (1975) and Alfonso Soriano (2002 and 2003) as the only players in Yankees history with a 30-30 season.
Despite missing a month with an oblique strain, Chisholm has posted career-highs in bWAR (4.2) and on-base percentage (.342) over 106 games. Chisholm’s .848 OPS marks his highest over a full season; he recorded an .860 OPS in 60 games three years ago.
It's fair AND it's gone
— MLB (@MLB) September 3, 2025
Jazz Chisholm Jr. crushes his 2nd HR of the night 💪 pic.twitter.com/88vcmTfucy
Not only is Chisholm terrorizing opposing pitching, but he’s doing so with one year of team control remaining. The Yankees don’t have to worry about Chisholm parlaying an excellent 2025 into a massive contract on the open market in two or three months.
However, Chisholm could force — and should force — the Yankees to go against the grain and extend their All-Star second baseman before hitting free agency next year.
The Yankees must consider extending Jazz Chisholm Jr. this winter
Unlike other organizations, the Yankees typically don’t extend players before their current contract expires. Instead, the Yankees prefer to negotiate in the window leading up to free agency; that’s why Juan Soto joined the crosstown Mets this past offseason and why other players, such as DJ LeMahieu, hit the open market before signing a new deal.
Several months before Jeter and closer Mariano Rivera became free agents in 2010, Yankees owner Hal Steinbrenner said it’s a “business policy” not to extend players or coaches. The Yankees re-signed both players, who finished their careers in the Bronx without suiting up for another team.
“I just don’t believe in contract extensions, and that’s throughout the organization, no matter who it is,” Steinbrenner told reporters in 2010. “Hopefully, nobody takes that personally. It’s just business.”
Jazz Chisholm Jr. slugs one into the bullpen! pic.twitter.com/8ORZRPmruo
— MLB (@MLB) August 29, 2025
Of course, the Yankees nearly broke that rule when they tried extending Aaron Judge ahead of the 2022 season. Those negotiations fell through, and Judge played that year as a pending free agent before inking a nine-year, $360 million deal that December.
Chisholm, 27, has done more than enough to earn a new contract. Not only has Chisholm provided a reliable left-handed bat in the middle of the order, but he’s also used his personality and charm to become a fan favorite. Although Chisholm still strikes out in 27.4% of his plate appearances, his walk rate has skyrocketed to a career-best 12.2%.
Barring an injury or disaster, Chisholm should have no shortage of suitors next offseason. If he wants to stay with the Yankees, and there’s no reason to believe that he’s already thinking of leaving, then it behooves both sides to start ironing out an extension.
The pressure is mounting on the Yankees to win a championship in the Judge era, and Chisholm continues proving that he’ll be a vital part of any title chase. For their sake, we suggest that the Yankees accept that fact rather than let Chisholm take the field on Opening Day 2026 in a contract year.