Early this offseason, the Boston Red Sox announced that one of their priorities outside of roster construction would be naming a general manager to serve under Craig Breslow. That hasn't happened yet, likely because their top candidate departed the organization for another.
Boston's former assistant GM, Paul Toboni, had been part of the Red Sox organization for 15 years, working his way up from a baseball operations intern to the top candidate for the GM job (subscription required). He was hired out from under Breslow's feet before he could name him GM.
The Washington Nationals signed Toboni to be their new president of baseball operations after they fired their previous one in the middle of the 2025 season. It's an excellent and earned promotion for Toboni, who immediately became the youngest man in charge of any team in MLB. He isn't the only key mind who left Boston this summer.
Former Red Sox director of pitching Justin Willard also departed the organization to become a pitching coach for the New York Mets. Willard was one of the main architects of Boston's revamped pitching program that began to take shape after Breslow's hiring, and his hard work has already shown in the Sox's recent drafting and trading strategies, and their surge in MLB-ready pitching depth.
Red Sox's constant free agent whiffs and bad decisions could be costing them more than just player talent
Both Toboni and Willard left the Red Sox for higher positions elsewhere, as almost anyone would do if they had a promotion lined up. But their departure this year, right around the same time (alongside some other notable personnel leaving in the minor leagues) raises some questions.
Toboni and Willard may have seen the writing on the wall for the Red Sox's Alex Bregman chase before it even started, and it's just pattern recognition — Boston hasn't offered top dollar to sign one of the best players in the game for years, despite its assertions that growing more competitive and re-signing Bregman were top priorities. In the face of certain failure in the Bregman market and in the wake of the Rafael Devers trade disaster, two of the Red Sox's top young minds got out while the getting was good. Boston has rebounded slightly by signing Ranger Suárez, but Bregman was a perfect infield candidate and it won't find another easily.
It's been well established that Breslow isn't the most popular guy among Red Sox employees, but other factors also may have led to Toboni and Willard's moves to other teams. The Red Sox's front office has been an enigma to many fans, reporters and insiders since their last World Series win in 2018. John Henry wanted to cut some payroll to focus on his other endeavors after his fourth title in 14 years, but now it seems like he's purposely blowing free agent pursuits.
Of course Bregman would demand a no-trade clause after seeing what the organization has done to elite players like Mookie Betts and Devers. And the Red Sox had the nerve not to extend him the no-trade clause while also offering him less money than the Cubs did. In the last half-decade, Boston has tried to conduct business in such a slimy way that players and front offices around the league are beginning to take notice — and it could've been one of the things that cost them their top GM candidate. No one wants to play or work for a losing team, and the Red Sox have been losing big for years.