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Craig Breslow, Red Sox Plan To Hire GM This Offseason

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With the 2025 season nearing its conclusion, teams around the league are beginning to turn their attention towards staffing changes during the offseason. The Orioles are known to be looking for a second-in-command for president of baseball operations Mike Elias, while the Nationals are looking for the successor to Mike Rizzo and have already begun contacting possible candidates. It seems the Red Sox will also be joining the fray looking for front office talent, as Rob Bradford of Audacy Sports writes that chief baseball officer Craig Breslow will “prioritize” finding a GM to serve as his second-in-command in the Red Sox front office this year after going the first two years of his tenure in Boston without one.

It’s hardly a surprise that Breslow would be looking for a number two. Breslow conducted an audit of the Red Sox front office early in his tenure with the organization, a decision which postponed his search for a second-in-command as it would necessarily involve evaluating the work of in-house candidates. That audit concluded last year, however, and the Red Sox still entered the 2025 campaign without hiring a GM. The Red Sox did hire Taylor Smith away from the Rays for an assistant GM role last winter, but that made Smith one of several assistant GMs already in the organization. At the time of Smith’s hire, there was some speculation that perhaps Smith was being brought into the fold to take over the responsibilities of assistant GM Paul Toboni, who was at the time viewed as the top internal candidate for the GM role.

No such promotion ultimately came to pass for Toboni, however, and now that Breslow is gearing up to hire a GM this winter it’s unclear if he (or any other internal Red Sox personnel, for that matter) will be considered as candidates for the job or not. At the time, Toboni was viewed as a candidate for a handful of vacancies around the game and promoting him could have served as a way to keep him in the organization. He ultimately remained in the organization with his same title, but now could once again be a hot commodity on the market for other clubs looking to add to their front offices.

Mark Feinsand of MLB.com writes that Toboni is a candidate for the Nationals’ vacant GM job, where he would replace former head of baseball operations Mike Rizzo. While the Red Sox would be able to offer Toboni that same title, it would come with significantly more responsibility in Washington given that the GM of the Nationals is the club’s top baseball operations position. Of course, it must be noted that it’s unclear whether Toboni has been asked to interview for the position or if he’s even been contacted at this point. Even so, the fact that Toboni is even under consideration to lead an organization’s baseball operations department, in conjunction with his name coming up in various other GM searches around the league in previous years, suggests that he’s well-regarded within the industry and could once again be a candidate for various opportunities around the game.

It should be noted that Breslow’s pool of talent from which he can draw from in his GM search will naturally be smaller given that the candidate he hires will not be given the top job in baseball operations. While the Nats have been connected to names such as Cubs GM Carter Hawkins, other organizations will typically block their executives from jumping ship for a lateral move. That means anyone who is currently the #2 of an organization with a president of baseball operations, such as Hawkins, would be unlikely to even be permitted to interview for the job as Breslow’s right-hand man.

Still, there are plenty of executives around the game in assistant GM roles and other lower-level positions who Breslow would be able to consider without much issue if he would like to hire from outside the Red Sox organization. Dodgers senior VP Josh Byrnes and Diamondbacks assistant GM Amiel Sawdaye are two other names reportedly connected to the Nationals’ GM search, and while they haven’t been connected to Boston’s GM job at this point they’re both examples of executives who currently hold positions that would not necessarily preclude them from being interviewed for the role.

Red Sox Promote Paul Toboni To Assistant GM

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The Red Sox are promoting Paul Toboni to assistant general manager, as first reported by Chris Cotillo of MassLive. The 33-year-old had held the title of vice president of amateur scouting and player development.

Toboni was among the internal options whom the Sox considered in their search for a new front office leader after dismissing Chaim Bloom. He’d have had to jump a number of people on the organizational hierarchy to land that position, which always made him a long shot for the top job. Nevertheless, he lands a promotion a few months later under new chief baseball officer Craig Breslow.

Boston now has four assistant GMs: Toboni, Raquel Ferreira, Eddie Romero and Mike Groopman. Toboni moved quickly into the upper ranks of the organization. A collegiate infielder at Cal, he was hired by the Sox as a scout in 2015. By 2020, he’d been tabbed to orchestrate the club’s amateur drafts — a role he held through 2022.

While the Sox have a number of assistant general managers, they don’t have anyone currently holding the GM title. Breslow suggested at the time of his hiring as chief baseball officer that he wasn’t in a rush to tab a GM, who would serve as his top assistant in the front office.

Red Sox Notes: Click, Interviews, Ferreira

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As the Red Sox continue to search for a new head of baseball operations after firing Chaim Bloom last month, names continue to emerge as potential candidates. One of the names receiving the most attention as things stand is former Astros GM James Click, who won the World Series with the club last year before parting ways with the organization last offseason.

A pursuit of Click is not without its complications, however. MassLive.com’s Chris Cotillo, while confirming Boston’s interest in Click for their top job, discusses some of the potential roadblocks that could leave Click’s interest in the role in doubt. Perhaps most notably, Cotillo points out the longtime friendship Click has with Bloom, noting that Bloom is the one who pushed the Rays to hire Click for his first job in a big league front office. While Cotillo makes clear that it seems unlikely Bloom would actively push Click away from interviewing for the position, he does note that the longstanding relationship between the two could give Click unique insight to the potential pitfalls of the position, particularly after Bloom’s sudden exit toward the end of the season.

Beyond Click’s relationship with Bloom, Cotillo notes a number of similarities between the Red Sox and Astros organizational structures that could turn him away from interest in Boston’s top job. After all, Click’s relationship with the Astros deteriorated in part thanks to his relationships with the club’s influential, strong-willed manager in Dusty Baker, and hands-on owner Jim Crane. Meanwhile, Red Sox manager Alex Cora is known to have a voice in Red Sox front office, including playing a role in the hiring process for the club’s next GM, and Cotillo notes that Red Sox ownership has had philosophical disputes with the front office across several regimes over the past decade.

Of course, Click is far from the only known candidate for the position. In terms of other external candidates, reports indicated earlier today that Twins GM Thad Levine, former Pirates GM Neal Huntington, and Cubs assistant GM Craig Breslow have all already interviewed for the role. That being said, the club has also involved internal candidates in their search. Assistant GM Eddie Romero is known to have previously interviewed for the position, with some reporting describing him as the “internal favorite.” According to Alex Speier of the Boston Globe, however, Romero is not the only internal candidate to be interviewed with both assistant GM Mike Groopman and VP of amateur scouting & player development Paul Toboni also having sat down for interviews with the organization. Cotillo adds that Toboni in particular is viewed as a “potential dark horse” in the running for Boston’s top job.

One internal candidate who won’t be interviewing for the position is assistant GM Raquel Ferreira, who declined the opportunity to interview for the position. As relayed by Cotillo, Ferreira cited family reasons in her decision not to interview for the club’s top job, and will remain in her current role in the organization. Ferreira has previously interviewed for top baseball operations jobs in other organizations, and did not close the door on pursuing a top front office job in the future, noting that “things could be different for me a year or two from now.”

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