Cubs linked to massive trade that would land them two All-Stars

The Chicago Cubs are in desperation mode with the MLB trade deadline inching closer and closer, and they may attempt to pull off a wild trade or to help get themselves back on track.

Since starting the season 27-12, the Cubs have gone just 13-25, and while they are still right in the thick of the National League playoff race, it’s clear that this team has debilitating holes that will continue to derail it unless they are patched.

The good news is that Chicago still has plenty of time between now and Aug. 3 to make some moves, and it seems like a certainty that the Cubs will do something.

Chicago badly needs help with its starting rotation, which has been among the league’s worst this season. It could also use another bat for its frustratingly inconsistent lineup, one that has received sparse production from top free-agent signing Alex Bregman.

The Play Tessie Podcast of WEEI has actually pitched a trade that would help the Cubs kill two birds with one stone, proposing that the Boston Red Sox send pitcher Sonny Gray, outfielder Jarren Duran and $10 million to Chicago in exchange for super-utility man Matt Shaw. But would the Cubs do this?

Chicago Cubs linked to huge trade with Boston Red Sox

On paper, this looks like a solid trade for the Cubbies. They would be landing a much-needed frontline starter in Gray, who has logged a 3.12 ERA this season and has made three All-Star appearances throughout his career. Then there’s Duran, who was an All-Star in 2024 and owns a lifetime .259/.320/.442 slash line. But there are layers here.

Gray is 36 years old and is headed toward free agency next offseason. And for as good as he has been this year, he has also shown serious signs of decline, averaging a career-low 7.1 strikeouts per nine innings. For reference, he posted a 10.0 K/9 as recently as last season.

As for Duran? He hasn’t been quite the same player since his breakout campaign that saw him slash .285/.342/.492 two years ago. That season, Duran led the majors in both doubles (48) and triples (14) while hitting 21 home runs. He regressed a bit in 2025, finishing with a .774 OPS. This year, he is slashing a meager .204/.262/.377.

Duran is still just 29 years old and is under club control through 2028, but perhaps his 2024 campaign was a bit of a fluke.

Considering how well Shaw has played here in 2026, the Cubs would probably like to squeeze more out of him than Gray and Duran in a trade.

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