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Despite the Red Sox’s historic winning run, there’s still a case for trading Sonny Gray

Jun 28, 2026; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Sonny Gray (54) delivers a pitch during the second inning against the New York Yankees at Fenway Park. Mandatory Credit: Paul Rutherford-Imagn Images
Jun 28, 2026; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Sonny Gray (54) delivers a pitch during the second inning against the New York Yankees at Fenway Park. Mandatory Credit: Paul Rutherford-Imagn Images | IMAGN IMAGES via Reuters Connect

If Boston Red Sox fans heard in mid-June that the team would have a winning record two weeks out from the trade deadline, most probably wouldn't have believed it. It would've been even harder to believe that they went on a 15-game winning streak to get there, but Boston has fully leaned into the improbable.

One of the most underwhelming teams in the American League at the beginning of the season went from an obvious trade deadline seller (with plenty of top talent that could've been dealt) to a buyer in about three weeks. Many teams that were hoping to reach out to Boston for trade deadline reinforcements such as Sonny Gray and Aroldis Chapman will now have to seek help elsewhere.

Unless the Red Sox decide that they still want to deal Gray. He's been their top starter all year to the tune of a 2.48 ERA, the fourth-best in MLB, a 1.12 WHIP, 90 strikeouts and 28 walks over 101.2 innings, but there's still a case for trading him.

Don't get us wrong: we're not advocating for trading Gray. Boston is the hottest team in baseball after the All-Star break and its gained so much ground in the American League that it can justify buying, but that doesn't mean Craig Breslow will go all-in.

Red Sox could still trade Sonny Gray at trade deadline because pool of sellers, elite talent will be so small

Because the standings are so tight in the middle of the AL, there are relatively few clear sellers in this year's deadline market. After the Detroit Tigers started their season almost as poorly as the Sox did, Tarik Skubal was expected to be the best pitcher available before August 3. But the Tigers have won nine of their last 12 games and sit 4.5 games back of the third Wild Card spot (as of July 21) so they may well end up buying.

Most insider intel suggests that Skubal won't be on the trade block — even Jeff Passan only gave him a 60 percent chance to be traded in his latest deadline rumor update. The teams hoping to land elite pitching for their playoff pushes, such as the Atlanta Braves and Chicago Cubs, will have a hard time finding worthy candidates this year, which is where Gray comes in.

Gray is on a one-year contract with the Red Sox and he'll be 37 years old in November. The odds Boston extends him are slim to none, especially since the 2027 season is under threat of a strike or lockout due to impending collective bargaining agreement negotiations between the league and players. The Red Sox could land an absolute haul of prospects, and maybe even some big leaguers, for Gray, as he could be the best pitcher on the market at the deadline. Breslow may want to prioritize the future since it's probably not the Sox's year to win it all — it feels like the distant past now, but remember how horrendous and unwatchable their offense was just one month ago.

Gray has a no-trade clause on his contract and he'd have to agree to any deal Breslow might want to pull with him. In June, Gray told reporters he was "open for a conversation" about waiving his no-trade clause, but things may have changed since the Sox took off on their historic win streak.

The Red Sox have to keep winning to justify buying before the trade deadline, which is easier said than done with matchups against the Toronto Blue Jays and Los Angeles Dodgers coming before August 3. If Boston falters even a bit, it could look to trade Gray for an incredible return because the pool of trade deadline sellers is so small.

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