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 be “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.
Early in Chapman’s career, it was hardly uncommon for his name to be in the conversation for the best relief arm in baseball at any given moment. The lefty made his big league debut back in 2010 as a member of the Reds and, over his first seven seasons in the majors, pitched to a dazzling 2.08 ERA with an even better 1.88 FIP and struck out 42.6% of his opponents faced. That includes a run of four consecutive All-Star appearances with Cincinnati from 2012-15 and a dominant 2016 season where he pitched to a 1.55 ERA with the Yankees and Cubs before throwing 15 2/3 innings for Chicago in the postseason en route to the first World Series championship of his career.