The Cubs don’t look eager to move Matt Shaw this offseason, and for good reason. They still believe in his upside, and he’s also lined up for a meaningful role in the outfield right now. But if Chicago does decide to explore a deal, the path could run straight through the Bronx.
The idea traces back to the trade deadline, when the Washington Nationals and Boston Red Sox pulled off a one-for-one swap that caught the Cubs’ attention. Boston sent controllable starting pitcher Connelly Early to Washington in exchange for controllable bat Curtis Mead. Afterward, reporting confirmed the Cubs had interest in Early, and there’s a real chance a similar deal could have happened if Shaw had been healthy at the deadline.
That’s where the Yankees enter the picture. New York doesn’t appear interested in a Jazz Chisholm Jr. reunion this offseason, and there’s also little appetite to keep rolling with the Ryan McMahon experiment.
That leaves the Yankees needing a third baseman, and the free-agent market doesn’t offer many clean answers. Shaw could fit that need.
The other reason this makes sense is the pitching surplus in New York. The expectation is that the Yankees could move a starter to help fill their offensive hole, and two names stand out: Will Warren and Ryan Weathers. Of the two, Warren seems a bit more likely to be available.
A straight-up Shaw-for-Warren deal has the kind of symmetry that makes sense for both sides. Warren is under control through 2030, while Shaw is controlled through 2031. The Yankees would get their third baseman, and the Cubs would land a young starter they can keep around for years.
Warren probably isn’t the arm who walks in and anchors the top of Chicago’s rotation. But the Cubs need multiple starting pitchers this winter, and he would give them a useful piece to work with.
His career strikeout rate is nearly 24%, and his ground-ball rate in 2026 was 44.2%. That profile gives Chicago something to think about if the teams ever get serious.
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