This Red Sox-Cubs Mock Trade Brings Matt Shaw to Boston

Spoiler: it's a big ask from Chicago

Sep 27, 2025; Chicago, Illinois, USA; Chicago Cubs third baseman Matt Shaw (6) runs back to the dugout during the first inning of a baseball game against the St. Louis Cardinals at Wrigley Field. Mandatory Credit: Kamil Krzaczynski-Imagn Images | Kamil Krzaczynski-Imagn Images

The time to make trades is quickly slipping away, and at some point, the Boston Red Sox have a big decision to make.

When it comes to acquiring any of the top infield targets they've been linked to, the Red Sox are going to have to give up more than they've been comfortable with all winter. Whether it's Matt Shaw, Nico Hoerner, or Isaac Paredes, there's going to be a big name leaving Boston if a deal gets done.

There seems to be a bit of momentum building for Shaw, if only because there's no momentum elsewhere. Red Sox insider Ari Alexander of WHDH-TV made an "educated guess" on Monday that Shaw was the most likely infield trade pickup for the Red Sox, a sentiment that is shared by many who cover the team.

Projected package to bring Shaw to Boston

Sep 27, 2025; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Connelly Early (71) pitches during the first inning against the Detroit Tigers at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images | Bob DeChiara-Imagn Images

If the Red Sox are intent on contending both this year and beyond, Shaw makes a lot of sense, as he comes with five years of control. But just because the Cubs are listening on both him and their second baseman, Hoerner, doesn't mean they're under pressure to let him go.

Boston would have to give the Cubs a rotation upgrade in the short term and some added prospect capital, whether the front office agreed that the value was fair on both sides, because that's all the Cubs are in a position to accept. Here's what it would have to look like:

Shaw comes with five years of control, while Early has all six of his. The 23-year-old Boston lefty, who trains with new Cubs third baseman Alex Bregman in the offseason, could slot in as Chicago's No. 5 starter on day one, which is why he's the headliner over any other pitcher in the Boston system.

A Red Sox fan could reasonably prefer Early this year over Shaw, even though the former is likely to start the year in Triple-A if he's not traded. But that's not what we're talking about here.

If Early, or perhaps fellow lefty Payton Tolle, isn't included in the trade, then the trade isn't happening. And if the trade isn't happening, there are going to be a lot of Red Sox fans angry about David Hamilton or Romy Gonzalez in the opening day lineup while Bregman gets introduced in Chicago.

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