The Chicago Cubs are setting up for a dramatic MLB trade deadline. The rumors and speculation are swirling around the team from all angles. The thing about Chicago is they have MLB playoff aspirations, but right now every MLB game is a fight, and if they want to make noise in the playoffs, it feels like the Cubs MUST acquire a starting pitcher.
Reports about a month ago from USA Today’s Bob Nightengale indicated that the Cubs may be willing to part with 24-year-old infielder Matt Shaw if it meant acquiring a front-line starter. Well, one name for the Cubs to consider is Boston Red Sox starter Sonny Gray, especially if the Red Sox head towards being sellers this summer.
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Should the Cubs Trade for Sonny Gray?
GettyNEW YORK, NEW YORK – JUNE 05: Sonny Gray #54 of the Boston Red Sox pitches during the first inning against the New York Yankees at Yankee Stadium on June 05, 2026 in New York City. (Photo by Jim McIsaac/Getty Images)
Sonny Gray is linked to a three-year, $75 million contract, but he has been stellar for the Boston Red Sox this season. While reports may indicate that the Red Sox are ‘not going to sell’, PBO Craig Breslow has been one of the most aggressive executives in MLB in terms of making trades.
ESPN’s Kiley McDaniel and Jeff Passan also just named the Red Sox as a top trade chip* for utilityman Matt Shaw:
“Shaw is higher on this list than far more productive players, which illustrates the value of club control,” wrote ESPN on Wednesday. “Not a free agent until after the 2031 season, Shaw has been just shy of a league-average hitter since his debut last season. Multiple teams believe that if given a full-time role — not available in Chicago with an infield of Bregman, Dansby Swanson and Nico Hoerner all locked up to long-term deals.”
So to piggyback off that concept, the Cubs SHOULD trade for Sonny Gray if the Red Sox will take a trade offer that consists of Matt Shaw and a pair of other prospects that could center around Kevin Alcantara and a depth-organizational piece.
Sonny Gray is a 3X MLB All-Star, and this season, Gray has an ERA of 3.03 over 62+ innings.
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Cubs Trade Package for Sonny Gray
As outlined, the Cubs offer the Red Sox Matt Shaw, Kevin Alcantara, and another top-30 prospect in exchange for Sonny Gray.
The Cubs have been continuously linked to starting pitchers this season, and expect that to continue with the injuries/inconsistent performances Chicago has received from its rotation.
Some other names that Chicago can consider in trades are Sany Alcantara, Joe Ryan, and potentially Tarik Skubal. However, there will be several starters made available by selling teams, and that’s where the Cubs should be looking to make a splash.
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