Why the Red Sox are targeting Cubs CEO Craig Breslow for the top job at Fenway Park

The Chicago Cubs expect Craig Breslow to be poached to manage another major league team at some point. The Cubs also realized that Breslow, a rookie 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 if Breslow is the right player, Breslow will have to make his own calculations about the pros and cons of working at Fenway Park. Breslow was in advanced discussions with the Red Sox, according to sources familiar with the search process, interviewing for their first job in baseball operations. However, this opportunity comes with many complicating factors for any external candidate.

The Red Sox were forced to fire 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 major league payroll, which A methodical process that still puts them in the American League Championship Series for 2021. Then the Red Sox fired Bloom last month with one season remaining on his five-year contract.

Boston will not be a blank slate. The Red Sox have already indicated that Alex Cora will return as manager next season. Their baseball operations department also includes 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 Gomez (Los Angeles Dodgers) — declined to interview for the position.

Breslow, 43, grew up in Connecticut and still lives in the Boston suburbs with his family. After a 12-year career as a left-handed player in the major leagues, Breslow discussed his options after playing for a selection 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 opportunity to learn more about baseball operations and pursue aspects that interested him. Breslow started with the Cubs in 2019, a time when the organization was moving toward sweeping changes in scouting and player development. The lack of young pitching talent was a major reason why the Cubs ultimately stagnated after winning the 2016 World Series.

Breslow became an authoritative figure in the promotion department, earning a series of promotions that most recently made him assistant general manager and senior vice president of promotion. He was given broad responsibilities, overseeing the rebuilding of the organization’s promotional 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 president Tom Ricketts gives baseball executives the freedom to allocate resources and structure the division the way 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 big bid to stay in a job that already carries a lot of influence.

The players always deserve credit for making this happen, but Breslow’s tenure saw the Cubs gain significant gains on the pitching side of the organization. Justin Steele emerged this year as a homegrown Cy Young Award candidate. Kyle Hendricks’ successful return included many collaborative elements within the promotional group. Adbert Alzolay and Javier Assad, two international free agents who took years to develop into contributors, helped the Cubs stay in contention for the playoffs until the penultimate day of the season.

Jordan Weeks, a 2021 first-round pick, made his major league debut in August and has won four straight games. Cade Horton, a 2022 first-round pick, is viewed as one of the top prospects in the sport. The Cubs now have a top-tier farm system, a bright future, and unfinished business.

Breslow is already on the path to landing Chris Young in charge of the Texas Rangers. Young, 44, is a Princeton graduate who 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 baseball’s chief executive at the end of the 2022 season. Young helped lead a turnaround that reshaped 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 an important employee is in no hurry to leave.

(Top photo by Craig Breslow on the 2023 Red Sox winter weekend: Billie Weiss/Boston Red Sox/Getty Images)