
The New York Yankees have a long list of impending free agents, some of whom are expected to land elsewhere.
Losing such notable names could derail the organization or force the Yankees to bring on necessary additions.
One of their free agent sluggers is now predicted to ship out to the Pittsburgh Pirates, leaving a massive roster gap.
Yankees’ Jazz Chisholm Jr. Predicted To Sign With Pirates

According to Kerry Miller of Bleacher Report, 28-year-old Jazz Chisholm Jr. could find his new home in Pittsburgh.
“With Lowe now headed for free agency, they need to add an infielder if they’re going to chase this sudden surge of competence,” he wrote. “Maybe they give Lowe a qualifying offer and he returns for one year at $23.15M. If he declines, perhaps they go the trade route again, pursuing Isaac Paredes from Houston or Ozzie Albies from Atlanta.
“Or maybe *record scratch* the Pirates sign one of the best free agents available in Jazz Chisholm Jr. It wouldn’t be a long-term, nine-figure monster of a deal. Pittsburgh extended both Griffin and Bryan Reynolds for north of $100M, but they don’t play that game in free agency.”
Combine Chisholm with the Pirates’ Oneil Cruz, and Pittsburgh could have several weapons in the lineup.

Of course, this is pure speculation, and no official signing has been announced or completed.
Snapshot of Chisholm’s MLB Career

During Chisholm’s 2026 campaign, he hit .231/.312/.399 with a .711 OPS and 19 homers through 137 games. He smacked 16 doubles, three triples and 55 RBIs.
The year before, he slashed .242/.332/.481 with a .813 OPS and 31 homers through 130 games. He logged 15 doubles, one triple and 80 RBIs along the way.
Chisholm made his MLB debut on Sept. 1, 2020.
He just wrapped up his seventh season in the big leagues.
His first five years were spent with the Miami Marlins, but once July 2024 rolled around, they traded him to the Yankees in exchange for Abrahan Ramirez, Agustín Ramírez and Jared Serna.

Chisholm has long been a key player for New York, but it seems as though his time in the Yankees’ iconic pinstripes has come to an end.
Pittsburgh could be an option, but several teams might be interested.
New York Yankees’ Silver Slugger Predicted To Sign With Pittsburgh Pirates