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LOS ANGELES, CALIFORNIA - APRIL 25: Craig Counsell #11 of the Chicago Cubs reacts as he walks back to the dugout after a pitching change during the fourth inning against the Los Angeles Dodgers at Dodger Stadium on April 25, 2026 in Los Angeles, California. (Photo by Harry How/Getty Images)
The Major League Baseball trade deadline is just over a month away, and the rumors and speculation about who could be on the move is starting to swirl.
For the Chicago Cubs, their biggest need remains a starting pitcher after several injuries to their pitching staff.
A recent trade idea from FanSided.com’s Christopher Kline proposes that the Cubs make a meaningful trade for Boston Red Sox starter Sonny Gray, who is on a three-year, $75 million contract and is a 3X MLB All-Star starter. Chicago has gotten back on track in recent games, but they recently endured a rough 10-game losing streak.
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Should the Cubs Target Sonny Gray?
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)
Due to a weak American League, it’s hard to say if the Red Sox will actually be sellers or not, but they remain in the cellar of the AL East, which has led to some speculation that they could move on from some of their tradeable assets, and Sonny Gray may be at the top of the list.
Sonny Gray is very familiar with the NL Central as well, playing for the St. Louis Cardinals for two seasons and pitching with the Cincinnati Reds for three seasons.
Here is why Kline believes the Cubs have a real shot at landing Gray:
“While this move seems shortsighted — it is, to be frank — sometimes you need to push your chips in. Chicago has been on a troubling slide these past couple weeks, but this is a very talented roster with a real chance to push deep into October. If the rotation can get even semi-healthy, the Cubs will stabilize quite a bit. Gray has pitched 165-plus innings in three straight seasons.”
In the trade idea, Kline proposes that the Cubbies could send Boston Matt Shaw in a player-swap deal. Shaw’s name has been floated around in trade rumors, and notably by USA Today’s Bob Nightengale, who believes Shaw could be a great trade chip for Chicago to land an ace starter.
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Sonny Gray this Season…
GettyBOSTON, MA – APRIL 20: Sonny Gray #54 of the Boston Red Sox pitches against the Detroit Tigers during the first inning at Fenway Park on April 20, 2026 in Boston, Massachusetts. (Photo By Winslow Townson/Getty Images)
Sonny Gray is having another solid MLB campaign in his 14th season in the pros.
He’s 6-1 with an ERA of 3.06 over 50 innings and 10 starts.
Things haven’t gone particularly well for the Red Sox this season, but Gray has been a bright spot and an overall good offseason trade. However, expect his name to carry some rumors over the next two months as the MLB trade deadline starts to heat up.
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TJ French covers the MLB for Heavy. TJ is a graduate of the University of Georgia. He has 2+ years of writing experience. Follow TJ French on X: @tj_french5 More about TJ French