Since the Boston Red Sox's elimination from the playoffs in its first week, multiple members of their coaching and front office staff have departed for new positions around MLB.
The most notable among them has been former assistant general manager Paul Toboni, whom the Red Sox planned to promote to GM had he stuck around. Toboni accepted a position as the Washington Nationals' president of baseball operations after their previous leader was fired in the middle of the 2025 season.
Former Red Sox director of pitching Justin Willard has also departed the organization for the New York Mets, Chris Hess, the former hitting coach for Double-A Portland, is leaving to become assistant hitting coach for the Miami Marlins, and the Nats are interviewing Sea Dogs manager Chad Epperson for their managerial vacancy, per Spencer Nusbaum of The Washington Post. Like Toboni, Willard is a huge loss for Boston, as he was one of the architects of its newly-revamped pitching program.
It's not often that this much talent departs from the same organization at once, and the sudden moves could mean a few things for Red Sox chief baseball officer Craig Breslow — either he's great at elevating his staffers to their full potential, or there's trouble going on behind the scenes.
Concerning Red Sox brain drain either reflects very well or very poorly on Craig Breslow
The Red Sox's player development and pitching staffs have been in the spotlight over the last two seasons due to their pipeline of emerging talent. Three top pitching prospects made their major league debuts for Boston this year (Hunter Dobbins, Payton Tolle and Connelly Early) and they each garnered considerable media attention. They, Roman Anthony, Marcelo Mayer and Kristian Campbell all stopped in Portland on their way to the big leagues.
Things in the Sox organization haven't all been roses this year, though. After the Rafael Devers trade, which was, ultimately, a result of poor communication, reports surfaced about disconnect and dysfunction in Boston's front office. The largest of which was a bombshell article from journalist Joon Lee on Yahoo! Sports, which states Breslow is difficult to work with and some of his moves have caused division in the front office.
There's no new evidence that points to the Red Sox's latest departure as a result of any of Breslow's actions, but it's not unreasonable to speculate given the organization's troubles in the last year. Regardless, the amount of brain drain Boston has seen so early this offseason is concerning, and it already has multiple roles to fill.