Boston Red Sox fans have critiqued second-year chief baseball officer Craig Breslow for his cold communication style. The events that led up to the Rafael Devers trade confirmed the worst of everyone's expectations.
Breslow admitted during the Red Sox's post-trade press conference that he could've communicated better with Devers, but that he's unsure if that would've changed the outcome of the situation (based on Devers' willingness to play first base for the Giants, this assertion seems false). Joon Lee's recent reporting for Yahoo! Sports revealed the depth of the Red Sox's communication issues goes way beyond Breslow.
Lee appeared on NBC Sports Boston and explained that a league source, whom the Red Sox recruited for a baseball operations job, was interviewed by an AI bot. It wasn't just the early stage of their interview process — they went through five rounds of the interview, just talking to a computer.
In Lee's June 16 piece, "Inside the 'absolute s*** show' that led to the Boston Red Sox's trade of Rafael Devers," he describes deep-rooted dysfunction in the Red Sox's front office, from poor communication to the isolation of higher-level personnel to the firings of longtime employees. He notes that when Breslow had the Red Sox organization audited six months after he was hired in May 2024, the culture in the office shifted toward "Wall Street efficiency."
Red Sox used an AI bot to conduct five rounds of an interview with a baseball operations candidate
For @NBCSBoston: the Red Sox dysfunction isn't just internal. It's affecting how they hire.
— Joon Lee (@joonlee) June 18, 2025
A league source was recruited by the Red Sox, only to go through five rounds of interviews with an AI without speaking to a single person.
Full segment: https://t.co/EdClPtH8ve pic.twitter.com/qrv3Kb5ofL
Using an AI bot to interview candidates is certainly something someone who claims to value Wall Street-level efficiency would do. Lee didn't report that Breslow implemented the AI interview process, but such a system seems in line with his robotic communication style. Red Sox reporter Ian Browne of MLB.com interviewed Breslow about the AI report, and he responded to Lee's story about a candidate speaking to only a computer for five rounds of their job interview.
“I think my short answer is, I'm not sure, because I know that I have had direct conversations with people. But like I said, if using this as kind of like a first filter, because the number of people who want to work with is so big, it makes sense. Now, I don't think we can make hiring decisions without actually talking to someone,” Breslow said.
AI interviews could also be a tool used by Fenway Sports Group, which Lee characterized as "hands off" in the Red Sox organization. No matter who implemented the practice, Lee's reporting shows the extent of the communication breakdown in Boston.