MLB Executive Questions Boston Red Sox Roster Construction

It hasn't been the start that anyone envisioned for the Boston Red Sox in 2026. They will enter play on Friday night at 9-16, the second-worst record in both Major League Baseball - and the American League. Boston came into the season with a rotation with massive expectations and an offense that was chock-full of question marks. Thus far, the pitching staff has massively underperformed, and the offense is proving that any questions about them coming into the season were more than valid. Their struggles out of the gate have led at least one MLB Executive to question Chief Baseball Officer Craig Breslow's roster construction. 

Breslow's plan of attack coming into the offseason appeared clear: retain Alex Bregman, add a power-hitter to the heart of the lineup to replace the production of Rafael Devers, and deal one of five outfielders for a front-line starter to pair with Garrett Crochet. After striking out with free agent Pete Alonso and showing little interest in Kyle Schwarber, Boston pivoted to retaining Bregman and adding a supplemental piece (Willson Contreras) to the lineup. When Bregman signed a five-year, $175 million deal with the Chicago Cubs in January, everything changed for Boston. Breslow made the decision to pivot to a team built on run prevention, handing money that appeared earmarked for Bregman to Ranger Suarez, making any path to a deal involving an outfielder much more difficult. 

Since last year's trade deadline, left fielder Jarren Duran has been the topic in any trade talks involving the Red Sox' outfield logjam, with many, including ESPN's Jeff Passan, thinking he would be the most likely of the group to be dealt. According to Passan, Breslow was placing a lofty price tag on the lefty sparkplug, "The Red Sox are valuing Duran more like the seven-win player of 2024 than his 4-win version in 2025," he said in ESPN's offseason primer. Adding "The Red Sox believe Duran is worth a front-of-the-rotation starter. At this point, no one has been willing to pay that," in a post on 'Threads'. 

The Red Sox, of course, held on to all five of their outfielders, leaving manager Alex Cora to juggle an imperfect roster on any given night. Now, it appears at least in the eyes of one executive, Breslow overplayed his hand. “You hold on to Duran all offseason and rebuff overtures for him,” an AL executive told MLB.com's Mark Feinsand. “I don’t know what you could even get for him right now.”

Duran has been in-and-out of the lineup and is off to a slow start at the plate, batting just .197 with a .568 OPS in 76 at-bats. Not only is he struggling at the plate, but he has also already had a run-in with a fan, something that has happened more than once in his career.

The idea that Breslow missed his window to trade Duran is more than fair. If he truly is an MVP-caliber player, like the Red Sox were valuing him as, shouldn't he be in the lineup every single day on a roster that ranks at or near the bottom of the league in so many offensive categories? As the season wears on, the constant juggling of the lineup becomes more and more untenable for Cora, continuing to lower the leverage that Breslow once had in trade discussions.

Duran will be in the lineup for Boston as they look to turn things around on Friday night. He'll be leading off and playing left field in the Red Sox series opener with the Baltimore Orioles. Brayan Bello gets the start opposite Brandon Young for Baltimore. First pitch from Camden Yards set for 7:05 p.m. ET. 

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