This Matt Shaw trade proposal lands Cubs a starter, solves Yankees' offseason problem

Realistically, there's not many scenarios where the Chicago Cubs are going to trade Matt Shaw this offseason. For one, the Cubs seem to still believe in Shaw's ceiling, and two, right now, Shaw is slated to have an important role in the outfield. That doesn't mean a trade won't happen, and it's possible the path to one is with the New York Yankees.

We must rewind back to the trade deadline. There was a one-for-one trade between the Washington Nationals and Boston Red Sox that had the Cubs' attention. The Red Sox swapped a controllable starting pitcher in Connelly Early for a controllable bat in Curtis Mead. Reporting after the fact has confirmed that the Cubs were interested in Early, and it's possible that a deal with the Red Sox could have been made if Shaw were healthy at the deadline.

Cubs may have only one sensible Matt Shaw trade partner (and it's Yankees)

Regardless, it seemed that the deal established the blueprint for why the Cubs could possibly trade Shaw this offseason. As it turns out, the Yankees are the perfect trade partner for this type of trade.

Between the Yankees having no interest in a Jazz Chisholm Jr. reunion this offseason, and little interest in continuing the Ryan McMahon experiment, they are going to be in the market for a third baseman. There's not a ton of options available on the free-agent market, and that could see them as an ideal suitor for Shaw.

But, the reason why New York stands out in this theory is that they have surplus of pitching. There's an expectation that the Yankees could trade from their rotation to address their needs on offense. Two trade options are Will Warren and Ryan Weathers. Between the two, it would seem Warren is slightly more likely to be deal.

With Warren under control through 2030, and Shaw under control through 2031, this feels like the one-for-one trade that could work between the two teams. The Yankees get their third baseman, and the Cubs get a controllable starting pitcher for the next several years.

Is Warren capable of sitting at top of the Cubs' rotation, probably not. But, the Cubs have to add multiple starting pitchers to their staff this winter. Warren would be an ideal target to pursue, and there's reasons within his metrics to suggest the fit could work. He has a career strikeout-rate of nearly 24%, and his ground-ball rate in 2026 was 44.2%. That combination feels like something the Cubs would be willing to work with.

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