NEW YORK — The Winter Meetings begin Sunday in Orlando. General managers and agents will pack hotel lobbies. Trade talks will heat up. And the New York Yankees might be ready to roll the dice on a move nobody saw coming.
At least, that is what one longtime insider suggested this week.
Bryan Hoch, who covers the Yankees for MLB.com, floated a stunning idea during his appearance on SNY’s Baseball Night in New York on Wednesday. He believes the club could explore trading Jazz Chisholm Jr. before free agency.
Yes, you read that right. The same Jazz Chisholm Jr. who just posted a 30-30 season. The same player who won his first Silver Slugger Award. The same guy fans have been begging the front office to extend.
So why would the Yankees even consider this?
Lukewarm contract talks spark trade chatter
Hoch did not mince words when asked why he would be open to trading Chisholm Jr. this offseason.
“I’d be willing to trade Jazz Chisholm at the Winter Meetings because, as of right now, it seems like they’re lukewarm about giving him a contract extension,” Hoch said. “Dynamic player. But do the Yankees see him as their future at second base? And if not, he could probably bring a significant return right here. He might be one of your best trade chips, and you can answer some other questions here.”
The numbers back up Chisholm’s value. He slashed .242/.332/.481 with an .813 OPS in 130 games during the 2025 season. He belted 31 home runs and stole 31 bases. He became only the third Yankee ever to hit 30 homers and steal 30 bags in the same year.
Bobby Bonds did it in 1975. Alfonso Soriano pulled it off in 2002 and 2003. Chisholm joins that exclusive club.
Still, general manager Brian Cashman has not started extension talks. He told reporters at the GM meetings last month that no conversations had taken place.
“We have not had any conversations outside of, you know, he’s looking forward to playing next year,” Cashman said. “He loves playing here. If you want to have a legitimate conversation about value, open to a longer-term conversation as well. But that’s the extent of it.”
Yankees rarely hand out early extensions
Here is the thing. The Yankees almost never extend players before free agency. Derek Jeter hit the open market. So did Mariano Rivera. Even Aaron Judge waited until after his record-breaking 2022 season to get his nine-year, $360 million deal.
The last notable extensions came in 2019. Aaron Hicks got seven years. Luis Severino signed for four. Both players eventually left the organization.
That leaves the Yankees with a choice. Pay Chisholm what he deserves. Let him walk for draft pick compensation. Or trade him now and get maximum return.
Trading Chisholm creates more problems than it solves
The obvious question surfaces immediately. Who plays second base?
The Yankees have no clear internal option. Jose Caballero and Oswaldo Cabrera will battle for shortstop with Anthony Volpe slated for late return after shoulder surgery. Top prospect George Lombard Jr. hit just .215 at Double-A Somerset and is not ready.
Trading Chisholm would force the front office to fill another hole on a roster that already needs pitching help and outfield depth.
Some suggest the Yankees could pivot to Bo Bichette. The Blue Jays shortstop is now a free agent and could slide to second base. But Bichette struggles defensively. His price tag might exceed what it would cost to simply extend Chisholm.
Ketel Marte is another name. But he turns 32 in October and carries a big contract. Trading for him means giving up prospects for a player exiting his prime.
What Chisholm brings to the Yankees lineup
Chisholm provides something the Yankees have lacked for years. He offers athleticism, speed and energy. He makes opposing pitchers uncomfortable on the bases.
He credited his success to the winning culture in the Bronx.
“The winning mentality, the winning atmosphere — the way everybody wants to win,” Chisholm said after winning the Silver Slugger. “It’s how I felt like I grew up playing baseball.”
Chisholm split time between second and third base in 2025. He posted a 4.4 WAR according to FanGraphs. He helped the Yankees lead the majors in runs scored with 849. The club hit a franchise-record 274 home runs.
Prospects remain the more likely trade pieces
To be fair, Hoch admitted that Spencer Jones and Jasson Dominguez are the more realistic trade chips heading into Orlando.
“Here’s a wild thought if the Yanks want to shake things up,” Hoch wrote in his newsletter. “Jazz Chisholm Jr. is entering his final season before free agency, and they’ve been lukewarm toward the suggestion of a contract extension.”
Wild thought is the key phrase. This is speculation, not a prediction.
But the possibility exists. And that tells you where the Yankees stand. They need bullpen help. They want to re-sign Cody Bellinger or land Kyle Tucker. Owner Hal Steinbrenner wants payroll flexibility.
Chisholm checks boxes on both sides. He can help the Yankees win. He can also reshape the roster if the front office chooses that path.
The Winter Meetings run from December 7 through December 10. Big names will move. Blockbuster deals will happen. Whether Chisholm is involved remains to be seen. But one thing is clear. The Yankees are willing to think big.
What do you think? Leave your comment below.
