NEW YORK — The first inning of Game 2 was barely underway when Jazz Chisholm Jr.‘s throw sailed. A Tampa Bay run scored on the error at Tropicana Field on Oct. 5. The Yankees infielder shamefully defended the mistake after the loss.
The Yankees committed four errors that night and lost 5-2. Two days later, the Rays finished a three-game sweep in the AL Division Series at Yankee Stadium.
Chisholm went 0-for-6 in the first two games. He started three of the Yankees’ five postseason games and finished with two hits. For the third straight October in pinstripes, he hit .182.
After the Game 3 loss, the pending free agent made clear where he wants to play. Chisholm, who grew up in the Bahamas as a Yankees fan following Derek Jeter, spoke about his future.
“I love it as a Yankee,” Chisholm said.
He also acknowledged the uncertainty.
“To see it maybe end here sucks, but it’s part of the business,” Chisholm said.
A season that slipped
Chisholm’s 2026 regular season fell well short of his 2025 breakout. He hit .231/.312/.399 with 19 homers, 55 RBIs and a career-high 41 stolen bases in 137 games. His 41 steals ranked third in the American League. His OPS+ was 97, and his wRC+ was 98.
The defensive numbers split. He finished minus-6 in Defensive Runs Saved at second base, 15th of 17 qualified second basemen. He graded better in Outs Above Average.
That split shows up in his value. FanGraphs credited him with 3.5 WAR. Baseball-Reference put him at 1.7.
A year earlier, he was an All-Star and a Silver Slugger winner. He hit .242/.332/.481 with 31 homers and 31 steals, posting a 125 wRC+ and 4.3 fWAR in 130 games. That season still ended with a Division Series loss to Toronto.
Now the Yankees face a decision on a 29-year-old who wants to stay. And an old warning about him has resurfaced.
Jeter and Mattingly tried first
NJ.com columnist Bob Klapisch claimed that the Yankees knew about concerns over Chisholm’s focus before they traded for him in July 2024.
Those concerns came from two Yankees icons. When Chisholm played for Miami, Jeter was the Marlins’ chief executive and part owner, and Don Mattingly was the manager.
“They both met with Chisholm on repeated occasions and begged him to get his head straight,” Klapisch said.
Klapisch described the message they delivered to the young infielder.
“‘You have superstar talent. You have to get your head right. You have to focus. You have to make this a priority.’ Not even they could get through,” Klapisch said.
The Yankees made the deal anyway, betting on their clubhouse.
“The Yankees knew all this when they traded for Jazz. It’s not like Chisholm’s reputation was a mystery to them,” Klapisch said.
Klapisch said the front office believed its veteran core could succeed where Jeter and Mattingly had not.
“But they thought that a clubhouse filled with veterans like Aaron Judge and Cody Bellinger and Gerrit Cole could get through to him,” Klapisch said.
What the trade cost
The Yankees acquired Chisholm on July 27, 2024, for three minor leaguers: catcher Agustín Ramírez, infielder Jared Serna and right-hander Abrahan Ramírez.
Agustin Ramirez reached the majors with Miami. He has a .232 career average with 26 homers and 90 RBIs in 741 at-bats, according to StatMuse. He slipped in 2026, hitting .235 with five homers and a .688 OPS.
By regular-season value, the deal has paid off. Chisholm produced a 132 wRC+ and 2.3 fWAR in 46 games after the 2024 trade. Across three seasons in New York, he totaled 10.1 fWAR in 313 games.
The October split
The bill has come due in the postseason.
Chisholm posted the same .182 postseason average in 2024, 2025 and 2026. Over the same stretch, the Yankees lost the 2024 World Series to the Dodgers and were knocked out in the 2025 and 2026 Division Series.
His 2026 October also included the Game 2 throwing error and an 0-for-6 start that helped bury the Yankees against Tampa Bay.
That gap is the core of the debate. The regular-season numbers justify the trade. The October numbers raise the questions Jeter and Mattingly flagged years ago.
Where things stand
Chisholm is set to become a free agent after the World Series. An executive told MLB.com he projects a three- to four-year deal at about $20 million per season, well short of Chisholm’s reported ask of eight to 10 years at $35 million annually.
The Yankees are considered unlikely to make him a qualifying offer of $23.15 million after his down year.
Their second base alternatives are already in place. Anthony Volpe played second late in the season, including in the postseason, with rookie George Lombard Jr. taking over at shortstop. Luis García Jr. is another internal option.
Detroit, which could lose Gleyber Torres in free agency, has been named a potential fit, along with Toronto, the Angels, San Diego and Cincinnati.
The Yankees have not announced a decision. For now, the warning from Jeter and Mattingly is back in the conversation as the club weighs whether to bring Chisholm back.
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