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MILWAUKEE, WISCONSIN - OCTOBER 06: Manager Craig Counsell of the Chicago Cubs looks on before game two of the National League Division Series against the Milwaukee Brewers at American Family Field on October 06, 2025 in Milwaukee, Wisconsin. (Photo by John Fisher/Getty Images)

The middle portion of May has rolled around, and the obvious concern for the Chicago Cubs (starting rotation) hasn’t reared its ugly head just yet. Chicago is 29-16 (just two games off the best record in MLB), and holds firm in first place in the National League Central, but the Milwaukee Brewers, as they often do, have been playing good baseball lately.

The Cubs must consider trading for recently acquired Boston Red Sox starter Sonny Gray, who has had his name featured in trade talks after the Red Sox dreaded start to this season.

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Cubs Should Target Sonny Gray via Trade

GettySonny Gray #54 of the Boston Red Sox throws a pitch against the Cincinnati Reds during the game at Great American Ball Park on March 28, 2026 in Cincinnati, Ohio. (Photo by Andy Lyons/Getty Images

Recently, SI.com MLB writer Ryan Shea proposed the idea of the Boston Red Sox trading Sonny Gray to the Chicago Cubs:

“A veteran like Sonny Gray provides exactly the kind of stability contending teams need when injuries hit the rotation. For a first-place Cubs team dealing with multiple starting pitching losses, Gray brings consistency, command, and the ability to steady the staff through a playoff race.”

Shea proposes that the Cubs would have to give up three players (RHP Brandon Birdsell # 16 Prospect,OF Kevin Alcántara # 5 Prospect, UTIL James Triantos # 9 Prospect).

There’s no doubt that it’s a big haul, and Sonny Gray is technically in the last season of his three-year, $75 million contract. He’s an aging starter, but has still shown a strong ability to be a strong presence in the rotation, and the Cubs could use a somewhat dominant right-handed starter.

His strikeout numbers are down, but Sonny Gray holds a 3.18 ERA for the Red Sox this season. He’s a three-time MLB All-Star.

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Is This a Fair Trade Proposal?

This is a trade proposal that the Boston Red Sox would likely accept, and that means it’s one that the Chicago Cubs must consider trading for Sonny Gray.

The early-season success has been awesome for the Cubs, but if they endure another real injury to a member of the rotation, things could take a turn.

While this trade proposal may not be fair on paper, the big hinging factor is if the Cubs are willing to let go of some of those top prospects that Shea mentions.

Chicago is still in a great spot considering its lineup is one of the best in baseball, but given the team’s World Series aspirations, it will continuously be linked to all the trade speculation and rumors.

And with names starting to surface and formulate as real trade candidates, the Cubs are going to be one of the most interesting teams to watch for, as they really have needs at all positions within the pitching staff.

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