The Chicago Cubs expected Craig Breslow to someday be hired to manage another major league team. The Cubs also knew Breslow, an up-and-coming executive with a Yale degree and a World Series pedigree, would choose his next opportunity carefully.
Just as the Boston Red Sox need to decide whether Breslow is a good fit, Breslow must also be making his own calculations about the pros and cons of working at Fenway Park. Breslow is in advanced talks with the Red Sox and is interviewing for the No. 1 job in baseball operations, according to a person familiar with the search process. However, that opportunity comes with some complicating factors for external candidates.
The Red Sox let go of Ben Cherington less than two years after winning the 2013 World Series. 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 major league payroll. This methodical process earned them a spot in the 2021 American League Championship Series. The Red Sox then released Bloom last month with one season left on his five-year contract.
Boston is not a blank canvas. The Red Sox have already indicated that Alex Cora will return as manager next season. The company’s baseball operations division includes several long-time employees in senior positions. Two current general managers with New England roots and backgrounds similar to Breslow’s, Sam Fuld (Philadelphia Phillies) and Brandon Gomez (Los Angeles Dodgers), declined to be interviewed.
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 relief pitcher in the majors, Breslow discussed his post-play options with a select group of teams, including 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 all aspects of baseball operations that interested him. Breslow joined the Cubs in 2019, at a time when the organization was heading toward fundamental changes in scouting and player development. A lack of young pitching talent was the main reason the Cubs ultimately stagnated after winning the 2016 World Series.
Breslow has become an authority on pitching, rising through the ranks and most recently serving as assistant general manager and senior vice president of pitching. He had a wide range of responsibilities, including overseeing the rebuilding of the organization’s pitching development infrastructure, evaluating free agents, and closely following 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 president Tom Ricketts has given team executives the freedom to allocate resources and structure departments as they see fit. If the Red Sox ultimately decide to make two executive hires, but without giving Breslow the top spot and full authority, the Cubs will have a considerable amount of money to keep him in his already influential position. They will be in a favorable position to make a favorable offer.
Players who make that happen always deserve credit, but Breslow’s tenure has seen the Cubs rack up significant accomplishments on the pitching side of the organization. Justin Steele has emerged as a homegrown Cy Young Award candidate this year. Kyle Hendricks’ successful comeback involved several collaborative elements within the pitching staff. Adbert Alzolay and Javier Assad, two international free agents, took years to develop into contributors and helped the Cubs stay in playoff contention until the penultimate day of the season.
2021 first-round pick Jordan Wicks made his major league debut in August and has since won four games. 2022 first-round pick Cade Horton is considered one of the most promising pitchers in the sport. The Cubs now have a top-tier farm system, a bright future and unfinished business.
Breslow is already on the same trajectory that landed Chris Young as manager of the Texas Rangers. Young, 44, graduated from Princeton University and pitched in the majors for 13 years before working in Major League Baseball. Young joined the Rangers as general manager after the 2020 season and became the franchise’s No. 1 baseball executive heading into the end of the 2022 season. Young was instrumental in a turnaround that re-established the Rangers as a World Series contender.
This is good for the Cubs organization. Either the Cubs helped develop an executive talented enough to run another iconic franchise, or they created a situation so good that a valuable employee wouldn’t leave in a hurry.
(Top photo of Craig Breslow at the 2023 Red Sox Winter Weekend: Billy Weiss/Boston Red Sox/Getty Images)
