Jewish Pitcher Named New Red Sox Executive

For the third time this century, the Boston Red Sox have hired a Jewish Yale University alum to be their head of baseball operations.

While the 2002 hiring of a then-28-year-old Theo Epstein ultimately proved instrumental in the Red Sox winning their first World Series in 86 years, the 2019 appointment of Chaim Bloom to the prestigious post fell drastically short of expectations as the Red Sox finished in last place three out of four years during his stewardship. Now, following Bloom’s dismissal this past September, Boston has handpicked Craig Breslow, the one-time medical school aspirant and former journeyman lefty reliever, to shepherd the franchise back to relevancy.

If nothing else, Breslow’s background as a former player (seven teams in 12 years) with an Ivy League pedigree (he graduated from Yale in 2002 with degrees in molecular biology and biochemistry, and deferred admission to the NYU School of Medicine to pursue a professional baseball career) makes him one of the more intriguing figures in baseball heading into the 2024 season.

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“I understand that some of you will see me as another Ivy League nerd with a baseball front office job. It’s true, I am that.” Breslow, a Trumbull, Conn., native who attended Congregation B’nai Israel in nearby Bridgeport, where he had his bar mitzvah in 1993, acknowledged during his Nov. 2 introductory press conference as Boston’s new head of baseball operations. “But I’m also a 13-year big leaguer and a 2013 Boston Red Sox World Series champion. I know what it takes to win here and I’m willing to make the hard decisions necessary to deliver.”

While his initial press conference with the Boston media was laden with the inevitable platitudes and praise of ownership — “The commitment to winning from ownership is not a question here” — Breslow, as one of the precious few baseball executives with former MLB playing experience, took a moment to wax poetic about the game that quickly became his livelihood upon leaving Yale a couple decades ago.

“I know what it’s like to put on a Red Sox jersey and jog through the bullpen gate across freshly cut outfield grass,” added Breslow, who last pitched in the big leagues in 2017 before working his way up the ranks of the Chicago Cubs front office the past few seasons. “I know what it’s like to stand on the mound in front of tens of thousands of the most passionate fans in the game, to feel the cool, fall breeze hit the Red Sox jersey. And I know what it’s like to hoist the World Series trophy overhead, the culmination of a group of people coming together to accomplish something that they couldn’t have alone.”

In his newly minted role, Breslow, who in 2008 started his Strike 3 Foundation to fund pediatric cancer research in honor of his older sister who survived pediatric thyroid cancer, will be the face of the team’s front office. In this sense, it’s hard to imagine anyone more well-suited for the role as the 43-year-old comes across as exceptionally well-spoken and bright. Known league wide as the smartest man in baseball during his playing days, Breslow, as his former Red Sox manager John Farrell once said, “uses words in a normal conversation that I’m not used to. When he starts to speak, some guys might not be thinking along with him.”

But he will also be Boston’s lead decision maker on players, coaches and personnel, an all-encompassing function in which he is a novice. With the Cubs, working under the wing of curse-busting/likely future Hall of Fame executive Epstein, Breslow served as director of strategic initiatives in 2019 before being promoted to director of pitching in 2020 and finally assistant general manager in 2021. But he was never charged with having to pull the trigger on a blockbuster trade that would jettison a wildly popular player elsewhere, and in effect, alter the trajectory of the franchise. Now he will have to do so for a team that not so long ago was a regular postseason contender, like the Braves, but whose ownership group’s perceived reluctance to land big-ticket free agents has left many fans, ones who pay rather steep prices for tickets and concessions at Fenway Park, feeling disillusioned.

“I know that we have some needs to fill on our major league roster,” Breslow responded when being pressed about whether the front office would be willing to shell out big dollars to overhaul the roster in free agency this winter. “I think that there are multiple ways to get there, and our job is to take as comprehensive a look as we can at all possible paths there.”

Just as there are questions about how Breslow will adjust to making executive decisions, so too are there people wondering how he will reconcile the two seemingly competing visions of baseball being a sport driven by statistical analytics and one that is still played by actual human beings.

“I think great decision makers are great synthesizers of information,” he made a point of saying. “That can look differently for different people, and particularly at different times. I think what I would like to represent is the ability to weigh different information streams and to engage in conversations out of the empathy of all parties. The experience that I have does give me a unique perspective on what it’s like to endure the challenges of a major league schedule, of a major league family, of a major league coaching staff. I also have a great appreciation for the ability of objective information to remain unbiased and consistent and disciplined.”

While reviving the fortunes of a once-dominant franchise can be a years long drawn-out process, Red Sox Nation is growing restless. Put another way, when Truist Park hosts the All-Star Game in 2025, New Englanders expect the Red Sox, on Breslow’s watch, to be well represented.