Inside The Red Sox

Red Sox's Roller Coaster Offseason Earns Surprising Grade From ESPN

Where does your final letter grade land?
Sep 15, 2025; St. Louis, Missouri, USA; St. Louis Cardinals first baseman Willson Contreras (40) celebrates after hitting a RBI single against the Cincinnati Reds in the sixth inning at Busch Stadium. Mandatory Credit: Joe Puetz-Imagn Images
Sep 15, 2025; St. Louis, Missouri, USA; St. Louis Cardinals first baseman Willson Contreras (40) celebrates after hitting a RBI single against the Cincinnati Reds in the sixth inning at Busch Stadium. Mandatory Credit: Joe Puetz-Imagn Images | Joe Puetz-Imagn Images

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There was hardly ever a dull moment during the Boston Red Sox's offseason.

For the most part, the moves were geared toward improving the roster -- Sonny Gray, Willson Contreras, Ranger Suárez, Caleb Durbin, and more all rolled into town. But losing Alex Bregman to the Chicago Cubs created plenty of strife in early January.

On Wednesday, ESPN's David Schoenfield gave all 30 teams letter grades for their offseasons, and Red Sox fans might be surprised to learn that the columnist awarded Boston with a straight "A."

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Did Red Sox really crush their offseason?

Sonny Gray
Sep 24, 2025; San Francisco, California, USA; St. Louis Cardinals starting pitcher Sonny Gray (54) delivers a pitch against the San Francisco Giants during the first inning at Oracle Park. Mandatory Credit: Neville E. Guard-Imagn Images | Neville E. Guard-Imagn Images

"I absolutely love this offseason from Craig Breslow and his staff," wrote Schoenfield. "Remember, the Red Sox now operate under a budget. Breslow can't light money on fire the way the Red Sox did during the late 2010s under Dave Dombrowski.

"No, they didn't re-sign Bregman, but the trade for Durbin gives them a player who projects to just one less win in value than Bregman -- a younger, faster, high-contact hitter making $30 million (less) in salary. The trades for Gray and Contreras bring in win-now veterans who also won't hemorrhage the long-term payroll. Suarez is a riskier bet on a five-year, $130 million deal, but he has been a consistent performer since 2021 with only his durability a concern."

From an overhead view, Schoenfield makes a lot of great points. With regards to the infield swap specifically, the time could well arrive that the Red Sox are grateful they got Durbin on a rookie deal instead of trying to outbid the Cubs, who were clearly hell-bent on getting Bregman this time around.

Unfortunately for the Red Sox's front office, those decisions don't exist in a vacuum. Distrust is still high between the Breslows and Sam Kennedys of the world and the Boston fan base, and it's because Boston will let a beloved player walk out the door, not offer him a no-trade clause, then act like it's a shocker that he ditched.

Still, it's impossible to deny how much better the pitching staff has gotten, and if a few young hitters take steps forward this year, Boston could be a much more complete team than a year ago.

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Published
Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@wtfsports.org