Craig Breslow, who pitched in relief for the Red Sox in 2006 and again from 2012-15, was named Boston’s chief baseball officer on Wednesday. Jim Mone/Associated Press

Seeking to hire a new lead baseball executive, the Red Sox encountered their share of trials and tribulations. As has been widely reported, the club was met with a string of rejections at the outset, with a number of candidates declining invitations to interview for the position.

Eventually, the Red Sox discovered their footing, conducting interviews with more than a half-dozen candidates before choosing Craig Breslow as their new chief baseball officer.

From assorted interviews with those familiar with the process, here’s how that unfolded over the last few weeks:

• In the initial stages of their search, the Red Sox decided to aim high with their outreach. In addition to previously reported targets such as Mike Hill, Jon Daniels, James Click and Derek Falvey who have all served as general managers or the president of baseball operations, the team sent out a feeler to a prominent current executive, who also declined to speak with them about the opening. Having swung for the fences early, the Red Sox then recalculated and targeted more obtainable choices.

• One industry source confirmed “it’s fair to say” the Red Sox were initially surprised by the number of rejections they received. Team President and CEO Sam Kennedy was almost offended when a reporter asked him if the lure of the job might be diminished. “This is the Boston Red Sox,’’ said Kennedy. “If you want to run a baseball organization, this is where you want to be. You want to be in Boston.” Turns out, that wasn’t a widely shared sentiment. Then again, as one industry source noted, that’s hardly unprecedented. “Teams always expect their (vacancies) are more desirable than they really are. That’s just how it goes.”

• Breslow was on the team’s radar almost from the outset, though early on he was hardly considered any sort of favorite or front-runner. He came recommended by some who are respected within the Red Sox organization, and was known to many in baseball operations from his time as a player in Boston. As the process got underway, he was identified as someone who was, at the very least, worth speaking to, if for no other reason than to get his perspective as a valued baseball mind and someone from outside the organization who could bring an unbiased look at things.


• Even as the search evolved, the Red Sox were open to including new candidates to the interview process. When Kim Ng walked away from the Miami Marlins, she was contacted soon after by the Red Sox. Ng told the Sox she wanted to take some time to think about her next role and passed on an interview. At the same time, the Red Sox requested permission to speak with Baltimore Orioles executive Sig Mejdal, the brilliant analytics expert who helped build the St. Louis Cardinals and contributed to the Houston Astros’ dynastic run before joining the Orioles with GM Mike Elias. But the Orioles, perhaps fearful of losing a key front office mind to a division rival, dragged their feet on the process and never provided the Sox with the go-ahead to speak with Mejdal.

• Late last week, the Red Sox narrowed the list of finalists to three: Breslow, Minnesota Twins GM Thad Levine and current Cleveland consultant (and former Pittsburgh Pirates GM) Neal Huntington. Other interviewees – current Red Sox assistant GM Eddie Romero, former San Francisco Giants manager Gabe Kapler, current vice president of scouting (and former scouting director) Paul Toboni and assistant GM Mike Groopman – were informed they were out of the running.

Red Sox principal owner John Henry has always relied on analytics in his business dealings, and Craig Breslow’s aptitude for metrics impressed Henry. Michael Dwyer/Associated Press

• Breslow first began Breslow first began to separate himself from the pack when, during the second round of interviews, he met with Red Sox principal owner John Henry. Henry, who has always relied greatly on analytics in his own business dealings and favors them when it comes to his baseball management team, was impressed by Breslow’s aptitude for metrics and how they should best be used and interpreted. Henry also was impressed with Breslow’s overall intellectual curiosity.

• Following the vetting from Henry, Breslow became the clear favorite. Initially, there were some reservations about putting Breslow in the No. 1 chair because of his relative inexperience. But as the process wore on, the Red Sox could not identify any of the other candidates as a suitable No. 1 to oversee Breslow in the second chair. Additionally, there was some concern that if the Red Sox offered anything less than the No. 1 job, the Chicago Cubs, for whom Breslow had worked for the previous four years as director of pitching development, might see an opening to retain him with a promotion. Finally, there was an internal consensus that if Breslow were to take the No. 2 role and the team enjoyed immediate success, another team would attempt to soon lure him away with an offer to be the primary decision-maker. Eventually, the Red Sox grew comfortable with the idea of making Breslow the chief baseball officer, while acknowledging that it may take a bit of time for him to fully grow into the position.

• There’s been no official word on the length or terms of Breslow’s contract. But it’s known that the Red Sox gave predecessor Chaim Bloom a five-year deal when he was hired in October of 2019, and there’s no reason to believe that Breslow got a deal different than that one.

• The expectation is that Breslow will not hire a general manager for some time; there’s no guarantee or mandate that he will, period. But the smart thing for him to do is get acquainted with the rest of the baseball operations staff. Those long-serving members can provide institutional knowledge while guiding him through his first offseason as a top executive, and, if necessary, his first season, too. Breslow’s on-the-job work history is in pitching development, so he’ll need some help when it comes to roster building. And others will be there to provide assistance on salary arbitration, free-agent negotiations and trade talk. Of those on staff, Romero is viewed as having the best chance of one day being promoted into a top role. But it’s also entirely possible that if Breslow chooses a GM, that pick could be external.

• It’s also possible that Breslow could hire a more experienced senior advisor – someone who has been a GM or top decision-maker elsewhere – to serve as a mentor and top evaluator. Theo Epstein, who took control of the Red Sox at 28, relied heavily on Bill Lajoie. Ben Cherington later had Allard Baird. Even the more established Dave Dombrowski had Frank Wren. Bloom, though he was open to the idea, never found the right fit or circumstance. It would seem that Breslow could use a veteran voice, but the Sox baseball operations department is already bloated in the eyes of some and adding another hire could be problematic.

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