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MLB Insider: Why selling remains the best course of action for the Boston Red Sox

Bullet point summary by AI One American League franchise is projected to act as a major seller ahead of the August 3 trade deadline despite a recent hot streak. The market could be especially rich with high-impact pitching and veteran bats available from contending teams holding out hope. The front office’s decisions on several key

MLB Insider: Why selling remains the best course of action for the Boston Red Sox

Bullet point summary by AI

  • One American League franchise is projected to act as a major seller ahead of the August 3 trade deadline despite a recent hot streak.
  • The market could be especially rich with high-impact pitching and veteran bats available from contending teams holding out hope.
  • The front office’s decisions on several key assets will shape the team’s rebuild timeline and future competitiveness.

After sweeping the New York Yankees at Fenway Park over the weekend, a question has been posed to me a few times: Should the Boston Red Sox maybe buy, not sell, ahead of the Aug. 3 trade deadline?

The answer is no. At least, for now.

One series doesn’t erase a season of disappointment from the Red Sox

Toronto Blue Jays v Boston Red Sox | Jaiden Tripi/GettyImages

At 36-46 and in last place in the American League East, the Red Sox remain far away from a playoff spot. They trail the division by 12 games. They are 4.5 games back of a Wild Card spot, which is entirely doable, even if they’ll have to leapfrog seemingly half the league to get there. But have the Red Sox shown any signs of a team that can legitimately compete for a World Series ring this year?

The only thing that should give Boston hope that maybe the season turns around is the pitching staff, which has been excellent lately. Factor in the eventual return of Garrett Crochet and maybe you’ve got something cooking. But this is a flawed Red Sox team. They have holes; they are far from perfect. So, too, is almost every team in the American League.

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I’ve advocated for the Red Sox to buy in the past, but this year in particular feels like a time where they can take advantage of what should be a seller’s market. There are only few teams ready to commit to selling, and one that many thought would join that list, the Houston Astros, are only a half game back in the Wild Card hunt and have a legitimate chance of winning the AL West.

If they don’t sell, that would remove Christian Walker, Isaac Paredes, Josh Hader and others from the trade market. Look all over the American League right now: On June 29, no team was more than seven games back in the Wild Card race. They all think they have a chance.

Which means that this is a position where Craig Breslow and the front office can capitalize in stockpiling assets for 2027 and beyond. 

Red Sox could be in position to clean up by selling at the trade deadline

New York Yankees vs. Boston Red Sox | Maddie Malhotra/Boston Red Sox/GettyImages

Aroldis Chapman will be incredibly coveted at the trade deadline, and if he reaches 40 innings pitched, his option for 2027 automatically becomes guaranteed — which would further enhance his value. If Hader isn’t available, Chapman would be one of, if not the, top relievers on the market. At 38, he’s a proven winner, and he has a 2.19 ERA and 32 strikeouts in 24.2 innings pitched.

Sonny Gray will draw strong interest from teams in a pitching market that will include Tarik Skubal, Freddy Peralta and Joe Ryan. He’s had an excellent year after being acquired from the St. Louis Cardinals, posting a 2.69 ERA in 15 starts, and would be a strong add for any team looking for a high-end pitcher to start a playoff game. It’s entirely possible he’s a rental – he has a $30 million mutual option for 2027 ($10 million buyout), which are almost never picked up – so that would factor into any potential return.

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Willson Contreras is also a highly interesting trade candidate who has had one of the best seasons of his career, hitting .281/.375/.523 with 17 home runs and 50 RBI. At this stage of his career, he’s a first baseman and designated hitter. But he can impact games, especially on offense, and provide toughness and leadership in the clubhouse.

Other trade assets include Jarren Durran, among others, though the Red Sox have placed a high price tag on the outfielder in years past and such a price could make a deal even more unlikely this year.

Plenty can change between now and Aug. 3. Before the Yankees sweep, almost everyone assumed that the Red Sox would surely sell. Now there’s hope; if they can continue to build off this series, perhaps they can turn what has been an incredibly disappointing season around. But until we see it, the best guess is that Breslow and the front office operate as sellers.

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