Chicago Cubs Proposed Trade for Red Sox $75 Million Pitcher Includes Matt Shaw

The Chicago Cubs have steadily been linked to acquiring pitchers via the MLB trade deadline.

Sitting five games back of the Milwaukee Brewers in the NL Central, the Cubs very much carry MLB playoff (and World Series) aspirations, but the way their pitching staff is currently constructed, it might not be enough.

Trades are a great opportunity to bolster the club down the stretch of the season, and one name that the Cubs need to consider is Boston Red Sox starter Sonny Gray, who is tied to a three-year, $75 million contract. Gray’s name has been dropped in many trade rumors, and USA Today’s Bob Nightengale recently released a rumors piece that includes the Red Sox coveted starter.

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Cubs Should Trade Matt Shaw for Sonny Gray

GettyBOSTON, MASSACHUSETTS – JUNE 28: Sonny Gray #54 of the Boston Red Sox throws in the first inning against the New York Yankees at Fenway Park on June 28, 2026 in Boston, Massachusetts. (Photo by Jaiden Tripi/Getty Images)

USA Today’s Bob Nightengale wrote (on 7/1): 

“Gray is 9-1 with a 2.69 ERA and may be the best pitcher traded not named Tarik Skubal. He has been everything the Red Sox could possibly have envisioned when they acquired him from the St. Louis Cardinals. The Cardinals even chipped in $20 million to cover the remaining $41 million on his contract.”

If the Cubs are to acquire Sonny Gray, they would likely have to include infielder Matt Shaw. Nightengale reported last month that Chicago may be willing to part with Shaw if it means acquiring a front-line starter. Well, Gray is a front-line starter, and he knows the NL Central very well.

In a proposed trade, Chicago would send Matt Shaw and prospect Jonathon Long to the Red Sox in exchange for Sonny Gray.

Remember, the Boston Red Sox are thought to be targeting a right-handed infielder via trade as well, which is what makes this trade work.

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Sonny Gray & Matt Shaw’s Trade Status

GettyMINNEAPOLIS, MINNESOTA – APRIL 14: Sonny Gray #54 of the Boston Red Sox pitches against the Minnesota Twins in the first inning at Target Field on April 14, 2026 in Minneapolis, Minnesota. (Photo by Ellen Schmidt/Getty Images)

The trade status of Matt Shaw still feels up in the air, and the same can be said for Sonny Gray.

Both the Red Sox and Cubs are likely going to want to wait until the very last moment to decide if they want to trade either of their coveted stars, but as of now, both Gray and Shaw stand out as top trade candidates on both clubs.

MLBTR.com’s Anthony Franco recently wrote (about Gray’s trade status): 

“Assuming the financials can be sorted out, Gray should be a target for teams looking for a veteran arm who’d slot into their playoff rotation. He carries a 2.95 ERA through 76 1/3 innings, and while he’s not striking out as many batters as he did in St. Louis, he’s getting more ground-balls to compensate. Gray has previously received a QO and is ineligible for a second, so the Sox wouldn’t receive any compensation for holding him for the remainder of the season.”

Keep an eye on both the Cubs and Red Sox this trade deadline, as both figure to be active in meaningful moves.

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