The New York Yankees enter this offseason with a clear set of priorities after another year of competing in a stacked American League East. General manager Brian Cashman and the front office have long emphasized building depth across the diamond while remaining open to creative moves that address specific roster holes without overpaying in free agency.
Pitching remains a relative strength for the club, with a rotation that includes several established arms and promising young arms ready to contribute. That surplus has historically allowed the Yankees to explore the trade market for position-player upgrades when the right opportunity presents itself, rather than forcing the issue on the open market.
Infield consistency has been a talking point in the Bronx for multiple seasons. While the team has options and has made adjustments in recent years, adding a controllable everyday contributor who can handle second base and provide versatility has been viewed as a logical next step for a club that wants to maximize its window of contention.
That conversation gained fresh traction this week when longtime Chicago baseball insider Bruce Levine of 104.3 The Score said the Yankees could be a natural trade partner for the Chicago Cubs as the Cubs look to add pitching. Levine specifically pointed to Cubs utility man Matt Shaw as a player who fits what New York could be seeking.
“I think you need two, two really good arms added and, and one of the ways is not free agency but trade,” Levine said on the radio.
“So the New York Yankees are a trade partner in my mind with the Chicago Cubs because they are in dire need of a second baseman and a good second baseman and the Cubs have one to offer in the way of Matt Shaw.”
Shaw, 25, was a first-round pick by the Cubs in 2023 out of the University of Maryland. He has shown the ability to play multiple infield and outfield spots and remains under club control for several more seasons, making him an attractive target for any team looking for a cost-controlled piece rather than a high-priced free agent.
Levine went further, suggesting the Cubs are likely to move Shaw this winter regardless of the partner.
“Matt Shaw I don’t think can go through this offseason without being included in a trade to bring back pitching for the Chicago Cubs,” he said. “You like to keep you like to hold onto him but I think that the the confidence the Cubs now have in Pedro Ramirez kinda supplants where he was at.”
From the Yankees’ side, the fit is straightforward. New York has the pitching inventory that Chicago has openly wanted to upgrade, while Shaw would give the Yankees a younger, athletic option who can play every day at second base or shift around the diamond as needed. That kind of flexibility has been valuable for Cashman’s clubs in recent years.
“So, with that in mind I think, I think Shaw is is gonna be dealt and getting a pitcher back from a very pitcher-deep team like the Seattle Mariners or the New York Yankees would make certainly the most sense,” Levine added.
The Mariners have also been floated as a potential landing spot for Shaw, given Seattle’s own pitching depth. For the Yankees, however, the connection carries extra weight because of the specific positional need Levine highlighted. A deal would not require New York to dip into its top-tier prospect capital if the return is primarily major-league or near-major-league pitching the Cubs value.
Shaw’s 2026 numbers were not overwhelming — he hit .237 with five home runs in 173 at-bats — but scouts and front offices have continued to value his defensive versatility, baserunning and remaining upside. He is still early in his big-league career and has not yet reached arbitration.
Yankees officials have not publicly commented on any specific interest in Shaw. The club typically keeps its winter conversations quiet until something is close to being finalized. Still, the combination of New York’s pitching surplus and the Cubs’ stated desire to add arms creates a logical framework that multiple analysts have noticed.
Any deal would also depend on how the Cubs view their internal options. Levine noted that prospect Pedro Ramirez has increased the organization’s comfort level with moving Shaw, potentially allowing Ramirez to handle a corner-outfield role while remaining capable of sliding back to the infield if needed.
For Yankees fans, the idea of adding a controllable middle-infield piece without surrendering a cornerstone starter is the type of low-risk, high-reward move that has defined some of the club’s more successful offseasons. Whether the front office pursues it remains to be seen, but the insider linkage has already put Shaw on the radar in the Bronx.
The offseason is still young, and both clubs have other avenues to address their respective needs. Free agency and additional trade possibilities will shape the landscape over the coming weeks. For now, Levine’s comments have given Yankees observers one more name to monitor as Cashman and his staff work through their winter checklist.
