The news of the day on Sunday was the shocking trade that saw the Boston Red Sox trade All-Star Rafael Devers to the San Francisco Giants for an underwhelming package of reclamation project pitchers, an organizational top 10 outfield prospect, and an international free agent who is still a few years from being Major League ready. There is plenty of indirect fallout for the Cubs, but the biggest connection may be the executive at the center of the Devers trade.
The reason why the Red Sox reached the point they did on Sunday ties back to this offseason, when Boston made an aggressive pursuit and signing of Alex Bregman. Bregman, an All-Star third baseman with a gold glove pedigree, forced Devers to go from playing third base to serving as Boston's designated hitter. Had Craig Breslow, the chief baseball officer of the Red Sox, fully communicated that plan to Devers before Bregman was signed, chances are we wouldn't get the news we had yesterday. Instead, Breslow botched the communications to Devers, resulting in the organization being at odds with their superstar for the duration of the season.
The Rafael Devers trade likely wipes away Craig Breslow regret for Cubs fans
It needs to be noted that his run with the Red Sox is the first time that Breslow has run a baseball organization. Prior to his arrival in Boston, Breslow was a part of the Cubs' front office under Theo Epstein and Jed Hoyer. Breslow has been credited for his influence on the Cubs' development of their pitching infrastructure. In fact, when Breslow left the organization, there was some regret that it wasn't Hoyer.
Now, Breslow's approval rating is sinking.
Here’s my updated Red Sox blame pie 🥧
— Sammy James🔺 (@HebHammer94) June 16, 2025
John Henry/Ownership: 45%
Craig Breslow: 45%
Rafael Devers: 10%
It is surprising that the one thing Breslow is failing at during his time in charge of the Red Sox baseball operations is communication. If nothing else, the one thing that Epstein was great at during his time as the Cubs' President of Baseball Operations was communication. Even Hoyer, who doesn't have the same backing from Cubs fans as Epstein does, has been great at communicating his actions to not only the public but, more importantly, internally.
Lmaoooo nico harrison has craig breslow at the table for most hated executive in sports https://t.co/XsMdOtNpdA
— eazyethan (@eazye2248) June 16, 2025
Breslow is among the Red Sox contingency expected to speak on Monday, but no amount of damage control will save him from the disdain Red Sox fans currently have for him.
