The Red Sox don’t have a GM search problem; they have a turnover-driven reputation problem, and no press release fixes that kind of damage.
On Sunday, the Athletics hired Taylor Smith, Boston’s assistant GM, to be their new President of Baseball Operations. Call it bigger than a nice pickup for a rebuilding club hunting a bargain executive: this is the second straight offseason a Red Sox assistant GM has left to run somebody else’s front office, following Paul Toboni’s exit to Washington last winter.
Fenway doesn’t want to say this math out loud, but it’s simple: two years ago, the Red Sox had five assistant GMs. Down to three now: Raquel Ferreira, Eddie Romero, and Michael Groopman, the three who are, for the moment, still answering their phones.
There’s more to this than losses at the top, either. Devin Pearson left alongside Toboni last year. Coverage keeps dropping that detail, treating these moves as isolated hires instead of connected dots in the same pattern.
Chaim Bloom’s old GM chair has been empty since he got fired in September. You’d think a franchise with Boston’s résumé could fill that seat by Thanksgiving. Instead, per CBS Sports, multiple targeted candidates have turned down interview requests entirely.
That’s the real tell. People don’t decline a meeting for one of the more visible jobs in the sport over a scheduling conflict; they decline it because the league is small, everybody talks, and the word on the Red Sox front office right now travels faster than Craig Breslow’s extension announcement did.
Beat writer Tyler Milliken laid out the pattern as plainly as it deserves:
Back to back years of the Red Sox having an Assistant GM hired to run another organization.
Paul Toboni to the Nationals last winter. Now, Taylor Smith taking over the A’s.
Curious to see who Smith potentially brings with him. Devin Pearson was a significant loss with Toboni. pic.twitter.com/4iSUsdG1ev
— Tyler Milliken (@tylermilliken_) October 19, 2026
Milliken wasn’t being dramatic. He was doing arithmetic. Two years, two assistant GMs, two different divisions now running front offices partly built on things those guys learned in Boston.
Stability under Breslow has been a question mark before, too. He fired Alex Cora back in May, and the clubhouse spent weeks sorting out who was actually steering the operation before Chad Tracy settled it on the field. Now the front office itself is the part that can’t settle down.
Fans want to argue about who the Red Sox should chase this winter. Wrong conversation. A farm system and a payroll don’t matter much if the people evaluating both keep walking out the door to work somewhere with less chaos attached to the job description. Rival front offices are beating Boston on stability, not salary, and stability happens to be the one thing ownership controls entirely on its own and still can’t deliver.
Roman Anthony can keep hitting the ball into the Monster seats every other night — good for him, good for the roster. None of it touches a front office that can’t keep its own assistant GMs through a full offseason, let alone convince outside candidates the top job is worth the migraine.
The Red Sox will hire somebody eventually. Somebody always says yes in the end. But “eventually settled for whoever was left standing” isn’t the search ownership drew up in September, and it sure isn’t a process a stable organization needs to run twice in two years.
