Here's the scenario that keeps Yankees fans up at night: Brian Cashman trades Jazz Chisholm Jr. to sign Bo Bichette.
It sounds absurd at first. Chisholm just delivered a 30-30 season—31 homers, 31 stolen bases, Gold Glove-caliber defense at second base. He earned his first Silver Slugger Award. He brought energy to a clubhouse that desperately needed it. Why would any reasonable front office ship that out?
Then you look at the contract situation, and suddenly the logic appears.
Chisholm is entering his final year of arbitration. The Yankees haven't extended him. At the Winter Meetings, Cashman called the team "open-minded" about potential trade discussions involving the second baseman. That's GM-speak for "we're listening."
According to Bryan Hoch of MLB.com, there's genuine uncertainty about whether New York sees Chisholm as the long-term answer at second. Teams have inquired. The door is cracked.
Enter Bichette.
The Blue Jays shortstop is coming off a bounce-back 2025 where he slashed .311/.357/.483 with 18 home runs and 181 hits. His elite contact skills—99th percentile expected batting average, 86th percentile strikeout rate—address everything the Yankees lineup lacks. He doesn't give away at-bats. He grinds.
ESPN's David Schoenfield predicted Bichette signs with New York on a five-year, $150 million contract. Bleacher Report's Kerry Miller suggested the Yankees' interest is real, particularly if they move Chisholm first to create financial and roster flexibility.
"Watch out for the Yankees," Miller wrote. "They only have Jazz Chisholm Jr. under contract for one more year, and there have been reports that teams have been asking what it would take for them to give him up."
The fit isn't perfect. Bichette has struggled defensively at shortstop—teams want him at second or third base, not short. That means either Anthony Volpe slides off his position or Bichette does. Neither scenario is ideal for a franchise that already has questions about Volpe's bat after a rough 2025 campaign.
But Bichette knows the Yankees organization intimately. His older brother Dante Jr. was a first-round pick who spent seven seasons in the system. The family connection exists. The familiarity is there.
According to MLB.com's Hoch, one Toronto person told him Bichette would be "a good clubhouse fit" and "would handle New York well."
The question isn't whether Bichette is talented—he is. The question is whether trading a 27-year-old who slugs .481 and plays premium defense for a 27-year-old with defensive limitations makes strategic sense.
Chisholm provides speed, power, and defensive range the Yankees can't easily replace. Bichette provides contact and consistency the Yankees desperately need. One isn't clearly better than the other. They're different.
Maybe Cashman keeps both. Maybe he trades Chisholm for pitching instead. Maybe Bichette signs elsewhere and this whole conversation evaporates.
But the rumors keep swirling. And in the Bronx, where championships are the only acceptable outcome, every option stays on the table.
Even the ones that seem crazy.