The Red Sox made clear nearly a month ago that they planned to hire a GM this offseason. At the time, Paul Toboni was an assistant GM for the club and immediately appeared to be the logical choice for the role among internal candidates and perhaps even the overall favorite. It didn’t take long, however, for that option to come off the table. Toboni was hired by the Nationals to serve as their president of baseball operations, taking over as their top executive. According to The Boston Globe’s Tim Healey, Toboni was not only the “heavy favorite” to serve as Craig Breslow’s #2 in Boston, but the club now plans to “take a step a back” this offseason to evaluate what they want to do with the role now that he is no longer an option.
That seems to leave the door cracked open for the possibility that the Red Sox will go without a GM serving under Breslow for a third consecutive season in 2026. That would be something of a shock given the club’s comments last month, but given the club’s apparent focus on Toboni for the role it’s at least possible that their decision to hire a GM was largely a way to promote him and keep someone viewed as a rising star around the game in the organization’s fold. That’s no longer an option, so perhaps the Red Sox could decide to once again leave the job vacant headed into 2026.
Of course, that’s hardly guaranteed and may not be the most prudent option. As Healey notes, Breslow called Toboni’s departure “a big loss” for the organization and noted that he had a hand in all areas of player development in both the majors and minors. Those responsibilities will presumably need to be taken over by someone else, and while Boston’s three remaining assistant GMs (Raquel Ferreira, Eddie Romero, and Mike Groopman) could share some of that load or a lower-level member of the staff could be promoted to fill Toboni’s shoes, an external hire who could be brought in by the allure of that vacant GM job could perhaps kill two birds with one stone by filling the job of Breslow’s #2 with someone who offers some of the same strengths Toboni would have offered.
In any case, the Red Sox likely won’t be in a rush to hire their next GM in the coming days. While they’ve been eliminated from postseason contention themselves, Breslow suggested that they’ll figure out how to handle the loss of Toboni and the vacant GM role “once things quiet down” and the postseason starts to wind down. That’s sensible enough, given the fact that potentially intriguing candidates from other organizations could be hard to pluck away until that team is eliminated from postseason contention.
In other Red Sox news, the club is facing two significant looming opt-out opportunities on the left side of their infield. Alex Bregman, of course, will have the opportunity to forgo the final two years and $80MM ($40MM of which is deferred money) on his contract and return to free agency. After a season where Bregman slashed .273/.360/.462 with 3.5 WAR according to both Baseball Reference and Fangraphs in 114 games, it seems like a fairly good bet that he’ll be taking that opportunity. For now, though, Bregman is staying mum about his plans. He told reporters (including Chris Cotillo of MassLive) on Thursday that he was “not even thinking about” his impending free agency in the aftermath of the club’s loss to the Yankees in Game 3 of the AL Wild Card series.
The same is true of shortstop Trevor Story, who told reporters (including Cotillo) that his impending decision was “not at the top of mind,” though he did acknowledge that he came to Boston in hopes of sticking around for a “long time.” Story has two years and $55MM guaranteed left on his contract, with $5MM of that coming in the form of a buyout on a $25MM club option for the 2028 season. While Bregman’s banner year seems likely to make him a lock to opt out, Story is a much more borderline case. He played just 163 games total for Boston between 2022 and 2024 with below average offensive numbers, but enjoyed a 2025 campaign where he played in 157 games while slashing .263/.308/.433 with 25 homers and 31 steals in 654 plate appearances as Boston’s starting shortstop. He also improved as the season went on, hitting .291/.336/.490 in 75 games from July 1 onward.
That’s the sort of production that makes it easy to imagine Story beating his current guarantee in free agency, particularly in a market with few quality shortstops outside of Bo Bichette. On the other hand, he’s headed into his age-33 season and has a long injury history that could raise some eyebrows about offering a long-term deal, while his roughly league average offense (101 wRC+) isn’t the sort of impressive production that spurs teams to invest a massive average annual value in a player. If both Bregman and Story were to walk this winter, that would leave the Red Sox with a deeply unsettled infield, though Kristian Campbell, Marcelo Mayer, Triston Casas, and Ceddanne Rafaela are among the young players in the organization who could theoretically pick up a glove somewhere on the dirt next year.
