Cubs would seal Craig Breslow's fate if latest Red Sox trade proposal comes to life

Generally, the Boston Red Sox have the impression of being a one-stop trade partner for the Chicago Cubs at the 2026 trade deadline. The Cubs are motivated buyers with a need in the starting rotation, and a need at the back of the bullpen. In terms of rentals, the Red Sox hold two of the better options for the Cubs to check that box.

Sonny Gray has been an oft-rumored target for the Cubs over the years, but the complication was that he was with the St. Louis Cardinals. It was hard to imagine a scenario where the Cardinals would be willing to ship Gray to the Cubs.

Now with the Red Sox, if Boston chooses to sell at the deadline, Gray is a clear fit for the Cubs. The same can be said for Aroldis Chapman. Chapman being the big trade deadline move the Cubs made in 2016. A decade later, Chapman remains one of the best closers in baseball.

Cubs have a one-stop 2026 trade deadline partner in Red Sox that feels like a pipe dream.

Given what the Cubs will be searching for ahead of the deadline, a deal where Jed Hoyer lands both Gray and Chapman has been a popular suggestion. It's a fun idea to consider, but one that doesn't match the reality of the Cubs farm system. It's improved but not to the extent they can pull off a single trade for both pitchers.

The proposal would be costly, and certainly more than that's been suggested on social media.

One thing to note, while Gray is an expensive rental, Chapman has a 2027 option that vests if he surpasses 40 innings pitched this season and passes a physical. He's less than 15 innings away from clearing that bar. The added year of control is going to drive up the price to trade for Chapman, and that is the primary reason why a package including Pedro Ramirez, Jordan Wicks, and Brooks Caple would be a laughable offer.

Ramirez certainly seems likely to be traded by the Cubs this summer, but as the headliner for Gray and Chapman, that feels like a reach. Jordan Wicks, meanwhile, has an uneven track record. Wicks would be an experienced arm the Red Sox could immediately put in their rotation, but not much more than that. As for Caple, his ceiling may be in the bullpen and not a starting rotation.

If the Cubs were able to sucker the Red Sox into this trade, it would seal Craig Breslow's fate. Breslow is already on shaky ground with the Red Sox, and honestly, that's probably the primary reason not expect this type of trade for the Cubs.

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