Key Voice in Red Sox Ownership Reportedly 'Disappointed' in Craig Breslow
The calendar has officially turned over to June, and despite lofty preseason expectations, the Boston Red Sox are 25-33 and last place in the AL East.
While shocking in some ways, Boston's underwhelming start was predicted by many who criticized Craig Breslow's clear failure to build a cohesive lineup with consistent offensive output. Now in his third season as chief baseball officer, the pressure is mounting for Breslow to field a winner, not just externally, but internally.
In a new article from Tim Healey of The Boston Globe, league sources identified key questions about Breslow's philosophy, personality, and recent handlings of front office and clubhouse dynamics. Most notably, multiple sources pointed to concerns from Red Sox former general manager and three-time World Series champion Theo Epstein.
"Theo Epstein has been disappointed by the Sox' intense analytical direction under Breslow, multiple league sources said. A minority owner and adviser who led the franchise to two World Series titles as GM, Epstein has long been a mentor to Breslow, hiring him to the Cubs front office and helping him get the Sox job," Healey wrote.
Are the Red Sox better off now than when they hired Craig Breslow?
— Tim Healey (@timbhealey) June 1, 2026
A deep dive into the state of the organization: pitching and hitting development, Ivy League Breslow vs. big league Breslow, free agency, Theo, records/spending, lots more. https://t.co/mf10XmQ8hi
Epstein, who earned a reputation as one of the greatest executives of all time for breaking two of the longest championship droughts in sports in Boston and Chicago, stepped away from his front office role with the Cubs in 2020. The 52-year-old now serves as part-owner and senior advisor for Fenway Sports Group alongside principal owner John Henry.
Considering Epstein's history with Breslow and his continued involvement and influence in the organization, even if in a hands-off role, his reported thoughts on the current regime are eye-opening.
When asked about his relationship with Epstein, Breslow told Healey that their communication "ebbs and flows."
Along with his ultra-analytical approach, one of the main critiques during Breslow's tenure has been an inability to bridge the gap between front office brass and players, something that was somewhat surprising considering Breslow spent 12 years in the league as a relief pitcher.
And while Breslow explained to Healey that he has made more of an effort to connect with players this season, league sources indicated that he would "benefit from having an interpreter" to handle the club's interpersonal affairs.
In his short tenure with the team, Breslow and his staff have shown an ability to draft and develop pitching at a high-level, as players like Connelly Early and Payton Tolle are already contributing to the big league club. But questions remain with the hitting side, and the Red Sox are still without significant contributions from top prospects Roman Anthony, Marcelo Mayer, and Kristian Campbell.
As evidenced by last season's Rafael Devers and Alex Bregman fiasco, there is more to being a GM than just evaluating talent. For Breslow, who has clearly made it a goal to improve in the qualitative side of his job, may be running out of time if the results do not show up soon.
At his celebrity golf tournament on Monday, Red Sox legend David Ortiz spoke about recent conversations he has had with Henry, saying that the team owner is "worried."
"We had a conversation. I can see. I've known John a long time, him and the whole team," Ortiz told The Associated Press. "They're working on figuring things out to get this ride better."
"He knows the direction of this team and he's worried about the team's situation more than what people think he is."
David Ortiz on John Henry being worried about the state of the Red Sox:
— Tyler Milliken (@tylermilliken_) June 1, 2026
"He knows the direction of this team and he's worried about the team's situation more than what people think he is… I sat down to talk to John, and he wants to figure it out. He wants to have the formula to… pic.twitter.com/ceQnMNWuD1
Henry, who is routinely met with "sell the team" chants at Fenway Park, has been known to be quick on the trigger with struggling executives. Breslow replaced Chaim Bloom as chief baseball officer, who only held the role for three seasons and was largely responsible for rebuilding the farm system. Before that, Henry moved on from Dave Dombrowski after just four years, one of which featured a World Series championship.
That is to say that Breslow could be the next in line of axed Red Sox executives, even if his firing of longtime manager Alex Cora bought him some extra time. As tension builds within and confidence wanes from outside, the next few months will be crucial in deciding the future of the Breslow-era Red Sox.
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This story was originally published June 1, 2026 at 2:23 PM.