Craig Breslow’s masterclass: How to lose Devers and Bregman in half a year

In Boston, 2025 was the kind of year that should be taught in front offices as a case study in what not to do.

Under Craig Breslow’s leadership, the Red Sox delivered a masterclass in mismanagement that’s still hard to wrap your head around: they signed Alex Bregman without telling Rafael Devers, then traded Devers… only for Bregman to reject them in the end.

The moment the two‑time World Series champion from Houston arrived, the fallout was immediate. Devers — a three‑time All‑Star and one of the faces of the franchise — didn’t just throw a fit; a full‑blown fracture opened up. The relationship was beyond repair, the kind of rift no soft‑spoken press release or forced Spring Training smile could fix. By June, the Dominican star was wearing a Giants uniform.

Karma came for the Red Sox

From there, the script turned into an MLB‑style Greek tragedy. Boston chose the quick fix: ship out Devers and put their faith in the newly arrived Bregman, who, on paper, looked like the answer. But he never fully clicked in Boston — and the gamble backfired spectacularly.

On Saturday, rumors that had been swirling for weeks became reality. Bregman declined the extension the Red Sox offered — he never meshed with the front office — and instead signed a five‑year deal with the Chicago Cubs. And just like that, Boston entered 2026 with no Bregman and no Devers.

In barely half a year, the Red Sox front office managed to lose two of the best third basemen in the league and look exposed in the process.

Craig Breslow closed the book, wiped the whiteboard clean, and left behind one final lesson: don’t do to others what you wouldn’t want done to you.

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