Chicago Cubs linked to wild Matt Shaw trade with Red Sox

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Chicago Cubs linked to wild Matt Shaw trade with Red Sox

Originally posted on ChiCitySports | By Matthew Schmidt | Last updated May 22, 2026 12:05 PM ET

The Chicago Cubs are mired in an absolutely miserable slump, having lost nine of their last 11 games to fall down to third place in the NL Central.

Oddly enough, this recent skid came on the heels of two 10-game winning streaks, so it has certainly been a strange season for the Cubs thus far.

All hope is not lost, though. Not by any stretch. Chicago is still a solid 29-21 heading into its three-game series with the Houston Astros beginning on Friday, and all it really needs is the right moves between now and the trade deadline to bolster its playoff chances and World Series hopes.

Because the Cubs’ starting rotation has been absolutely decimated by injuries, Chicago is expected to pursue at least one starting pitcher before Aug. 3, and luckily for Jed Hoyer, there should be plenty of them available.

On that note, Ryan O’Rourke of Cubbies Crib has linked the Cubs to a wild trade with the Boston Red Sox featuring Matt Shaw as the centerpiece.

Chicago Cubs connected to wild Matt Shaw trade

May 10, 2026; Arlington, Texas, USA; Chicago Cubs third baseman Matt Shaw (6) fields a ground ball during the first inning against the Texas Rangers at Globe Life Field. Mandatory Credit: Raymond Carlin III-Imagn Images

The Red Sox have quite a few pitchers that may interest Chicago, and while veteran Sonny Gray is the most obvious candidate, O’Rourke shockingly mentioned youngsters Connelly Early and Payton Tolle as potential targets for the Cubs.

“Infield help appears to, once again, be something they could use, and that’s where Shaw could come in,” O’Rourke wrote. “The fit isn’t quite as obvious as it once was, but it’s still worth checking to see how willing [Craig] Breslow would be to do a challenge trade. In a perfect world, Shaw would be the centerpiece for a deal involving one of Connelly Early or Payton Tolle, giving the Cubs a controllable, high-end young arm they can continue working with for years to come.”

Now, it should be noted that O’Rourke qualified his statement by saying a Tolle trade would be unlikely, but he thinks Boston would be more willing to move one of its young hurler than one might expect because of the amount of pitching talent the Red Sox have within their organization.

Early would be a more likely piece for Boston to trade, although he was ranked as the 52nd-best prospect in baseball by Baseball America heading into 2026 and has pitched to the tune of a 3.33 ERA and 1.185 WHIP thus far. So would the Sox really move him at this point?

Shaw seems like an obvious trade candidate for Chicago given that there really isn’t room for him in the infield, and the Red Sox have expressed interest in him in the past. But I’m not so sure Boston would include either of its top two young pitchers in such a deal.

This article first appeared on ChiCitySports and was syndicated with permission.

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