The Chicago Cubs assumed Craig Breslow would eventually be poached to manage another major league team. The Cubs also understood that Breslow, an up-and-coming manager with a Yale degree and a World Series pedigree, would be selective about his next opportunity.
Just as the Boston Red Sox must determine whether Breslow is the right fit, Breslow must make his own calculations about the pros and cons of working at Fenway Park. According to sources familiar with the search process, Breslow was in advanced discussions with the Red Sox and was interviewing for their No. 1 job in baseball operations. However, this opportunity comes with several complicating factors for any external candidate.
The Red Sox fired 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 administration their major league payroll, a methodical process that still got them into the 2021 American League Championship Series. The Red Sox then released Bloom last month with one season left on his five-year contract.
Boston will not be a blank canvas. The Red Sox have already signaled that Alex Cora will return as manager next season. Their baseball department also employs several long-time employees in high-level positions. Two current general managers with New England roots and similar resumes to Breslow — Sam Fuld (Philadelphia Phillies) and Brandon Gomes (Los Angeles Dodgers) — declined to interview for the job.
Craig Breslow spent 12 years in the major leagues and retired after the 2017 season. (Brad Rempel/USA Today)
Breslow, 43, grew up in Connecticut and still lives with his family in a Boston suburb. After a 12-year career as a left-handed reliever in the majors, Breslow discussed his postgame options with a select group of teams that included the Cubs, Red Sox and New York Yankees.
Theo Epstein personally recruited Breslow to the Cubs’ front office, giving him the opportunity to learn more about baseball operations and pursue any aspects that interested him. Breslow started with the Cubs in 2019, a time when the organization was heading toward sweeping changes in scouting and player development. The lack of young pitching talent was one of the main reasons the Cubs ultimately stagnated after winning the 2016 World Series.
Breslow became an influential figure in the pitching department and received a series of promotions, most recently making him assistant general manager and senior vice president of pitching. He assumed wide-ranging responsibilities, overseeing the rebuilding of the organization’s pitching development infrastructure, evaluating free agents and remaining close to the day-to-day operations of the major league club.
Breslow has close 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 is giving his baseball executives the freedom to allocate resources and structure the department as they see fit. Should 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 influence .
The players always deserve the credit for making it happen, but Breslow’s tenure has seen the Cubs make major gains on the pitching side of the organization. Justin Steele emerged as a homegrown candidate for the Cy Young Award this year. Kyle Hendricks’ successful comeback included several elements of collaboration 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 second-to-last day of the season.
Jordan Wicks, a 2021 first-round pick, made his major league debut in August and won four straight games. Cade Horton, a 2022 first-round pick, is considered one of the best pitching prospects in the game. The Cubs now have a world-class farm system, a bright future and unfinished business.
Breslow is already on the path that led Chris Young to coach the Texas Rangers. Young, 44, is a Princeton graduate who played 13 years in the majors before working for Major League Baseball. Young joined the Rangers as general manager after the 2020 season and became their No. 1 baseball manager late in the 2022 season. Young helped engineer the turnaround that made the Rangers a World Series contender again.
That’s a good picture for the Cubs organization. Either the Cubs helped develop a talented executive to the point where he could lead another storied franchise, or they created a situation so good that a valued employee is in no hurry to leave.
(Top photo of Craig Breslow at Red Sox 2023 Winter Weekend: Billie Weiss / Boston Red Sox / Getty Images)