Craig Breslow just laid it all out. The Boston Red Sox Chief Baseball Officer admitted his “executive leadership circle” is “down not just bodies, but down really talented people,” laying bare the issues within the organization’s front office despite a late-season surge.
The Executive Drain
Remember all those media reports before Boston’s season-saving 15-game win streak? Yeah, when it looked like Breslow was on the chopping block, they painted a picture of a “near-reclusive CBO” who “trusted few people in the front office and alienated most others.” Winning usually fixes everything, right? It definitely put a lot of those concerns to rest. But here’s the kicker: the front office still has some massive holes. The General Manager role has been vacant since way back in 2023. And it gets worse: two high-ranking assistant GMs are gone and haven’t really been replaced. Paul Toboni, who got hired to lead the Nationals last fall, and Taylor Smith, who just dipped for the A’s after Breslow himself hired him just two years ago. That’s a huge hit to institutional knowledge and talent!
Who’s Next Out the Door?
Breslow isn’t just worried about finding a power bat this offseason. He’s making front office hiring a priority. The guy knows what’s up, saying, “It is pretty clear that that executive leadership circle is down not just bodies, but down really talented people. And we’ve got to find the right people to emerge and to put into place there.” That’s a pretty stark admission. And it’s not just the big-shot executives. Dana LeVangie, a Massachusetts native who’s been with the Red Sox since they drafted him in 1991, rising from pitching coach to the scouting department, is also leaving for a similar role with the Royals. He “needs to be replaced now, too.” Breslow isn’t mincing words about the stakes: “The inconvenient piece is that we need to put a great team on the field and we need to win more games in 2027 than we did in 2026. Losing leadership like Taylor and Paul makes that harder, but we have to do everything we can to replace them.” It sounds like they’re scrambling just to keep pace.
Rookie of the Year Snub?
While the Red Sox try to figure out who’s going to run their front office, MLB is busy handing out major awards this week. Tonight, it’s the Rookie of the Year announcement, and Payton Tolle is a finalist! Now, he’s probably not taking home the hardware, especially with how good Kevin McGonigle was this year. But Tolle did snag some serious praise from former Yankees ace CC Sabathia, who said, “I love watching him, and I love his personality. I don’t think I could have pitched the way he does. I was always way more emotional and upset. It’s fun to see him have that disposition.” That’s high praise from an absolute legend! Tolle is already at the top of the rotation alongside Garrett Crochet, so the future looks bright for him on the mound, even if a shiny new trophy isn’t in the cards tonight.
So, the Rookie of the Year gets announced tonight. For the Red Sox, the real drama is just starting. Can Breslow actually find the right people to fill these massive holes in the front office *and* land that power bat he mentioned? 2027 is going to be a wild ride trying to “win more games” with a front office that’s clearly struggling to staff up.
This article was created with AI assistance and published under Seattle On Tap’s editorial standards. See our Editorial Policy.
Originally reported by Over the Monster.
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