Red Sox vowed a long search but quickly locked on and secured Craig Breslow

It was four years to the day.

On Oct. 24, 2019, the Boston Red Sox chose Chaim Bloom as their next head of baseball operations. He would not officially take the reins until the following week, but once he had the offer, the job was his.

On Oct. 24, 2023, the Red Sox chose Bloom’s successor. On Thursday, the team offered its top job to Cubs assistant general manager Craig Breslow. He is expected to be introduced as the new head of baseball operations in the coming days.

Red Sox president Sam Kennedy had promised a broader search than last time — “One that frankly could take a while,” he said — but in the end, the Red Sox chose Breslow even more quickly than they chose Bloom. The search for Dave Dombrowski’s replacement took 46 days. The search for Bloom’s took 40.

According to multiple people with knowledge of the process, Breslow was the only candidate to receive a second interview. He’s been described as a favorite of Red Sox ownership from the very beginning, and — perhaps not coincidentally — also a favorite of former Red Sox GM Theo Epstein, whose opinion still carries weight in the organization and who has long touted Breslow’s potential as an executive.

“We don’t have a predetermined set of qualifications necessarily that we’re looking for,” Kennedy said at the end of the season. “But we do have a targeted list of individuals that we think will be able to help get us back where we belong in the American League East.”

Many of those individuals declined to interview for the position, which is not unusual for this sort of hiring process, but the extent of it did catch the attention of many in the industry who felt the Red Sox were having a hard time rounding up qualified candidates. In retrospect, some now see Breslow, 43, as a favorite for the job all along. He checks a lot of boxes the Red Sox seem to value.

For one, Breslow is familiar with the Boston market. Not only did he play parts of five seasons with the Red Sox, but he’s continued to live in nearby Newton, Mass., and worked remotely from home through much of his Cubs tenure. He’s also a Yale graduate, often noted for his intelligence and for his familiarity with analytics and technology, two essentials of the modern game. In that way, some of his resume lines up with Bloom’s.

But Breslow is also a former player, specifically a pitcher, and pitching development has been a Red Sox organizational weakness for several seasons under multiple heads of baseball operations. According to multiple people close to Breslow, he had no interest in leaving the Cubs for a secondary job — he wasn’t going to be a pitching coordinator or any other assistant — which would have been seen as a lateral move even if it came with a title bump. If the Red Sox really wanted him, they had little choice but to offer Breslow the top job.

Some in the organization have expressed concern about Breslow’s relative lack of experience and the potential that he could keep pushing the team further to the analytic side of player evaluation and roster construction. Red Sox assistant general manager Eddie Romero, who has an extensive scouting background, was considered by some inside the organization to be the internal favorite for the job but was passed over yet again in favor of an outside hire with less experience.

Breslow was still pitching as recently as 2018 and joined Epstein in the Cubs front office in 2019. In 2020, he was promoted to assistant general manager and vice president of pitching. He’s never run a baseball operations department, which leaves some elements of his leadership style unknown, though people in the Cubs organization have noted that Breslow was involved in aspects beyond pitching. He worked with their farm system, their draft room, their big-league coaching staff, and helped with free-agent negotiations.

Pitching, though, has been Breslow’s area of expertise throughout his baseball life, something the Red Sox surely valued in their evaluation of him as a priority target to take over as head of baseball operations.

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Breslow, a Connecticut native, has a long history with the Red Sox. (Jonathan Moore / Getty Images)

Jon Lester debuted in 2006 and Clay Buchholz in 2007, but after that the Red Sox went more than a decade without drafting and developing another consistent, long-term big-league starter. Impact position players rose through the system with some frequency — from Mookie Betts to Rafael Devers to Triston Casas — but effective pitchers, especially starters, remained few and far between. That problem remained a point of concern and emphasis during Bloom’s past four years as chief baseball officer.

Internally, the Red Sox believe they’ve made headway in that regard. The organization in recent years shifted its player development philosophy to be more proactive and aggressive with its pitching prospects, and the team might have graduated its latest rotation fixture in 24-year-old Brayan Bello, who was the team’s most consistent starter much of last season. The rise of Kutter Crawford and the second-half performance of prospect Wikelman Gonzalez are also signs of progress on the mound.

But earlier this offseason — even before a new head of baseball operations was in place — the Red Sox let go of longtime pitching coach Dave Bush, who’d been a key voice in the organization’s pitching program for eight years, four of them on the big-league staff. The team also decided not to bring back Triple-A pitching coach Paul Abbott, who’d been working in the organization for 13 years.

Clearly, the organization was working toward a pitching overhaul regardless of the person in charge.

Now the person in charge is a former big-league pitcher who worked extensively to overhaul the pitching program of his previous franchise. It’s not hard to compare Breslow to first-year Rangers general manager Chris Young, another former pitcher with an Ivy League education who had little front-office experience before replacing Jon Daniels as the head of baseball operations late last season. Young already has the Rangers in the World Series.

The Red Sox clearly are expecting a similarly fast turnaround from Breslow. It remains to be seen what changes he will make to a front office that’s had little turnover beyond the top seat. The team has said it’s open to hiring or promoting a No. 2 to work directly under its new head of baseball operations, but Breslow presumably will have considerable say in who that might be and what the role might entail.

For now, it’s just like four years ago. The Red Sox have a new head of baseball operations, and again it’s an outside hire who’s never had the top job. The team warned of a potentially lengthy search process but instead seemed to have locked in on a particular candidate before moving quickly to put him in charge of making them contenders once more.

(Top photo of Breslow: Billie Weiss / Boston Red Sox / Getty Images)

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