Yankees Weigh High-Risk Moves in Pursuit of Roster Stability and Playoff Firepower
The Yankees are at a crossroads this offseason, and the front office knows it. With a roster that’s talented but top-heavy, and a fan base hungry for October success, Brian Cashman and company are reportedly exploring a few bold moves - some more calculated than others.
Trading Jazz Chisholm Jr. and Signing Bo Bichette? That’s a Big Swing
One of the more intriguing - and risky - ideas floating around the Bronx involves flipping Jazz Chisholm Jr. while his trade value is high and pivoting toward Bo Bichette as a free agent solution at second base. That’s not just a roster tweak - it’s a philosophical shift.
Chisholm brings electricity. He’s a 30-30 threat with elite speed, growing defensive chops, and the kind of athleticism that makes highlight reels feel routine. But he’s also nearing the end of arbitration with no extension in place, which puts the Yankees in a familiar spot: do they pay up long-term, or cash out now?
Enter Bichette. The Blue Jays shortstop has long been known for his bat-to-ball skills and high-contact approach - traits the Yankees sorely lacked at times last season.
The idea would be to move Bichette to second base, where his glove might be less of a liability, and plug him in ahead of Aaron Judge in the lineup. On paper, that’s a stabilizing move.
In practice, it’s a gamble.
Bichette's recent defensive metrics haven’t inspired confidence, and his mobility has taken a hit due to injuries. Asking him to shift positions and stay healthy over a long season is a lot to bank on - especially if Chisholm goes elsewhere and flourishes.
This is the kind of move that could look brilliant in July or backfire by May. It all depends on whether the Yankees believe consistency at the plate is worth trading away raw athleticism and upside.
Matt Strahm Could Be the Bullpen Boost the Yankees Need
While the Yankees weigh big-picture moves, there’s also a more under-the-radar fix that could pay off in the short term: lefty reliever Matt Strahm.
The Phillies’ veteran quietly delivered another strong season, flashing a balanced pitch mix, elite command, and the ability to miss bats while limiting walks. For a Yankees bullpen that’s lacked reliable left-handed depth, Strahm checks a lot of boxes. He’s not a flamethrower, but he knows how to pitch - and that matters in late-game situations.
Strahm would likely slide into a setup role behind David Bednar, giving Aaron Boone another trusted arm to bridge the gap to the ninth. And with just one year left on his deal, he fits the Yankees’ recent preference for short-term financial flexibility. If the Phillies are open to a deal and the price is right, this is exactly the kind of move that could quietly stabilize a shaky bullpen.
Yankees Risk Losing Cody Bellinger to Mets’ Aggression
Then there’s the looming threat across town. The Mets, under David Stearns, are staying aggressive - and they’ve got their eyes on Cody Bellinger. If they land him, it would be another gut punch for the Yankees in what’s becoming a pattern of hesitation.
Bellinger is the kind of player who fits just about anywhere. He brings power from the left side, can play all three outfield spots (and first base in a pinch), and has postseason experience.
For the Mets, he’s a potential cornerstone as they prepare for life after Pete Alonso. For the Yankees, he was supposed to be a major target - but their measured approach may cost them again.
This isn’t just about one player. It’s about perception.
The Yankees have made a habit of sticking to their valuations, but in a market where stars are commanding premium prices, that strategy can leave you empty-handed. Meanwhile, the Mets are acting like the big-market team they are, willing to spend and take risks.
If Bellinger ends up in Queens, it won’t just sting - it’ll be another signal that the balance of power in New York baseball is shifting. And unless the Yankees start matching that urgency, they could find themselves watching the postseason from home again.
Bottom Line: The Yankees have options this winter - but none of them come without risk. Whether it’s betting on Bo Bichette’s bat, shoring up the bullpen with a savvy trade for Matt Strahm, or losing out on Cody Bellinger to a more aggressive rival, the decisions made over the next few weeks could shape the franchise’s direction for years to come. The question is: will the Yankees play it safe, or finally push their chips to the center of the table?