The Chicago Cubs expected that Craig Breslow would be poached to run another major-league team at some point. The Cubs also understood that Breslow, a rising executive with a Yale degree and a World Series pedigree, would be selective about his next opportunity.
Just as the Boston Red Sox will have to determine whether Breslow is the right fit, Breslow must be making his own calculations about the pluses and minuses of working at Fenway Park. Breslow has been in advanced discussions with the Red Sox, according to sources familiar with the search process, interviewing for their No. 1 job in baseball operations. That opportunity, however, comes with several complicating factors for any external candidate.
The Red Sox forced out Ben Cherington within two years of their 2013 World Series title. The Red Sox fired Dave Dombrowski less than a year after winning the 2018 World Series. The Red Sox hired Chaim Bloom to rebuild their farm system and manage their major-league payroll, a methodical process that still put them in the 2021 American League Championship Series. The Red Sox then fired Bloom last month with one season remaining on his five-year contract.
Boston will not be a blank canvas. The Red Sox already signaled that Alex Cora will return as manager next season. Their baseball operations department also carries several longtime employees in high-level positions. Two current general managers with New England roots and resumes similar to Breslow’s — Sam Fuld (Philadelphia Phillies) and Brandon Gomes (Los Angeles Dodgers) — declined to interview for the job.
Breslow, 43, grew up in Connecticut and still lives in suburban Boston with his family. After a 12-year career as a left-handed reliever in the majors, Breslow discussed his post-playing options with a select group of teams that included the Cubs, Red Sox and New York Yankees.
Theo Epstein personally recruited Breslow to join the Cubs front office, giving him the chance to learn more about baseball operations and pursue whatever aspects interested him. Breslow started with the Cubs in 2019, a time when the organization was headed toward sweeping changes in scouting and player development. The lack of young pitching talent was a major reason why the Cubs eventually stagnated after winning the 2016 World Series.
Breslow became an authoritative figure in the pitching department, earning a series of promotions that most recently made him an assistant general manager and the senior vice president of pitching. He earned broad responsibilities, overseeing a rebuild of the organization’s pitching development infrastructure, evaluating free agents and staying close to the day-to-day operations of the major-league club.
Breslow has strong relationships with president of baseball operations Jed Hoyer and manager David Ross, who played with Breslow on the Red Sox team that won the 2013 World Series. Cubs chairman Tom Ricketts gives his baseball executives the freedom to allocate resources and structure the department however they see fit. If the Red Sox ultimately decide to hire two executives — but without giving Breslow the top spot and full authority — the Cubs would be well-positioned to make a substantial offer to stay in a job that already carries a lot of clout.
The players always deserve the credit for making it happen, but Breslow’s tenure has seen the Cubs accumulate big gains on the pitching side of the organization. Justin Steele emerged this year as a homegrown Cy Young Award candidate. Kyle Hendricks’ successful comeback involved several collaborative elements within the pitching group. Adbert Alzolay and Javier Assad, two international free agents who took years to develop into contributors, helped the Cubs stay in playoff contention until the penultimate day of the season.
Jordan Wicks, a 2021 first-round pick, made his major-league debut in August and won four games down the stretch. Cade Horton, a 2022 first-round pick, is viewed as one of the sport’s best pitching prospects. The Cubs now have a top-tier farm system, a bright future and unfinished business.
Breslow is already on the kind of trajectory that put Chris Young in charge of the Texas Rangers. Young, 44, is a Princeton graduate who pitched in the majors for 13 years before working for Major League Baseball. Young joined the Rangers as a general manager after the 2020 season and became their No. 1 baseball executive toward the end of the 2022 season. Young helped lead the turnaround that remade the Rangers as a World Series contender.
This is a good look for the Cubs organization. Either the Cubs helped develop a talented executive to the point of running another iconic franchise or they created such a good situation that a valued employee is not in a rush to leave.
(Top photo of Craig Breslow at the 2023 Red Sox Winter Weekend: Billie Weiss / Boston Red Sox / Getty Images)