Promising Update Drops on Red Sox-Cubs Trade Talks

It's hard to find the perfect trade for the Boston Red Sox right now. But in terms of needs matching up with other teams, the Chicago Cubs stand out.

Boston has three starting infielders it feels good about; Chicago has five. Meanwhile, the Red Sox are fixing to start top rookie pitching prospects Payton Tolle and Connelly Early at Triple-A this year, because they've added three potential high-end starters in trades and free agency.

So with only a week and change to go before spring training starts, what are the odds the Red Sox might spring a trade for either second baseman Nico Hoerner or third baseman/utility man Matt Shaw?

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Where Red Sox, Cubs seemingly stand

Oct 6, 2025; Milwaukee, Wisconsin, USA; Chicago Cubs third baseman Matt Shaw (6) warms up before the game against the Milwaukee Brewers during game two of the NLDS round for the 2025 MLB playoffs at American Family Field. Mandatory Credit: Michael McLoone-Imagn Images | Michael McLoone-Imagn Images

On Saturday, Alex Speier of The Boston Globe reported that Chicago is at least willing to listen on both Hoerner and Shaw, which makes sense because they're a few weeks removed from poaching Alex Bregman from Boston in free agency. Certainly, though, there's no guarantee that the Red Sox will be willing to match the sticker price.

"According to sources, the Cubs have been open to conversations on both, and the Sox are among the many teams that have checked in about the two players," wrote Speier.

"Chicago doesn’t feel a need to move either player given the possibility of having Shaw — a 23-year-old Worcester Academy alum whom the Cubs drafted in the first round in 2023 — bounce between the infield and outfield in a super-utility role. Still, as the Cubs look to build short- and long-term rotation depth, the Sox do have the well-regarded young pitching to create a potential match."

Tolle and Early are the obvious candidates to move based on Speier's reporting here. Both could be front-line starters if they hit their ceilings, but right now, Tolle's ceiling is so high it's practically undefined, while Early has the higher floor and would be a more reliable addition to a big-league rotation right now.

If the Red Sox have to give up one of those two and more, though,to trade for one of these Chicago infielders? That may well be where Craig Breslow draws the line.

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