Five years before he was considered — and ultimately hired — to be chief baseball officer of the Red Sox, Craig Breslow had his first interview to join the club’s front office in a much different capacity.
Following a 2018 season spent pitching at various levels of the Blue Jays’ minor league system, Breslow knew his playing career was almost certainly finished after 576 major league appearances over parts of 12 seasons with seven different clubs. Then 38, Breslow was ready to transition into the next chapter of his life but wasn’t sure exactly what his post-playing career would look like. A Yale graduate with degrees in molecular biophysics and biochemistry who was often described as “the smartest man in baseball” during his playing career, Breslow was going to have options across many disciplines when he retired. His heart, however, was set on staying in the game.
“My window to go to medical school or join some kind of start-up at close to 40 years old and trying to compete with others who were 20 years younger than me had probably passed,” Breslow said during a conversation at last week’s Winter Meetings in Nashville. “Baseball was what I knew the best. It’s what I was most passionate about and it’s where I felt like I could have the most impact in the shortest amount of time. But I wasn’t sure where that would go or where it would end up.”
For Breslow, the natural starting point in the fall of 2018 was to connect with executives and coaches he had known as a player in an effort to see if there was a role that interested him within an organization. At the time, he was open to coaching, front office, data-driven and hybrid roles. In conversations with a handful of clubs, including the Red Sox, Yankees and Cubs, Breslow sought out to find the right fit.
“I wasn’t totally sure what I wanted to do,” he said. “I think there was a chance that I was going to find myself interested in getting back on the field or some kind of hybrid-type role, or, potentially, set a course to be in the front office in earnest. I felt like some kind of multidisciplinary exposure was going to be what gave me the chance to start to figure out what I wanted to be when I grew up.”
The Dave Dombrowski-led Red Sox, fresh off a World Series title, were eager to talk to Breslow, who had impressed front office members with his intellect during two stints with the team (2006, 2012-2015). At the time, Boston’s top executives didn’t have any specific front office jobs open but, according to one source with knowledge of the conversations, wanted Breslow involved in the team’s pitching department in some fashion.
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Dombrowski was excited by the prospect of adding Breslow to the group. That the former reliever was a Connecticut native with a home in Newton made the fit appear logical to both sides.
“A very intelligent individual,” Dombrowski said. “Played in the big leagues. Pitched in the big leagues for a long time. Very intelligent individual, well-spoken, knowledgeable, local. So there were a lot of factors that played into the situation of why we talked to him. We thought he would be able to help.”
The interview, however, did not go as smoothly as the sides had hoped before meeting. The Red Sox went into the sit-down with high hopes of hiring Breslow before he — according to an industry source with knowledge of the conversations — irked club executives by presenting a self-made job design for a powerful, broad role within the organization and came off as inflexible instead of being open to other roles the team might have had in mind. Boston’s team of experienced, championship-winning officials quickly realized there wasn’t a fit for Breslow, who some in the organization thought had asked for too big of a role considering his complete lack of front office experience.
In Nashville, neither Breslow nor Dombrowski described the meeting in a negative way. Dombrowski said he liked Breslow, who he did not know before interviewing him, “a great deal.” In the end, said the Phillies president of baseball operations, the Red Sox and Breslow simply were not a fit for each other.
“We knew he was smart. We knew he was a knowledgeable baseball guy,” Dombrowski said. “So it was really more a matter of, ‘Where does everything take us?’ And at that time, we just didn’t have really the right match for him.”
The Theo Epstein-led Cubs, however, did. In Jan. 2019, shortly after Breslow talked with the Red Sox, Chicago hired Breslow as director of strategic initiatives in their baseball operations department with the goal of “helping to evaluate and implement data-based processes throughout all facets of baseball operations” and “supporting the organization’s pitching infrastructure in player development and the majors.” In more than four years with the Cubs, Breslow — who rose to assistant GM in Nov. 2020 — let Breslow experience all facets of the operation, including some work on the field, some scouting responsibilities and participating in processes like arbitration and baseball operations.
“It was a crash course in in baseball operations,” Breslow said. “I think it prepared me for what was to come.”
A half-decade later, Breslow doesn’t have any regrets about how the interview process went, in Boston or anywhere else. He believes talking to the teams he did — and ultimately landing his job with the Cubs — helped him rise to a top baseball operations job so quickly after retirement.
“I think a number of people here, with Dave at the forefront, were really helpful in helping me identify what exposure and path I might want to set for myself and what opportunities might exist here in Boston,” Breslow said. “I think there was overlap and there was plenty of mutual interest. At the same time, I felt the exposure that Theo was willing to afford me at a time where I wasn’t entirely certain what type of commitment I could make, or was willing to make, was just a better fit for me and my family.
“What I think I came to realize is just how much I didn’t know, and how valuable the experience of living through trades and roster construction and free agency and arbitration and sending players down,” he added. “I had been sent down plenty. I had been designated (for assignment) plenty. But I was never the person making those decisions.”
In the fall of 2018, it would have been difficult to envision the Red Sox twice changing baseball operations heads over the next five years, especially considering Dombrowski had just won a title. It may have been even harder to imagine Breslow, having been as inexperienced and green as he was during his initial interview with the club back then, running the show so soon. But that’s what happened, with Breslow serving as the successor to Dombrowski’s successor, Chaim Bloom.
“I would still say that there’s a lot I don’t know. That hasn’t changed,” Breslow said. “But I’ve been fortunate to work alongside and under some people who have been really successful in this game and can lean on them for counsel and advice and consider them mentors in many ways. I feel like I’m as prepared as one can be, knowing that one can never be completely prepared.
“In some ways, it came full circle and now I ended up back in Boston.”
