In the Alex Bregman deal, the Boston Red Sox played with fire and burned their fingers.
In other words, Craig Breslow and the Sox have failed to retain Bregman in Boston, which had become the club's top priority. As a result, the Bostonnais find themselves with their backs to the wall, and by focusing too much on a single issue, they've watched the parade of free agents go by until now.
If we go back to last year, when the relationship between the Red Sox and Rafael Devers was already on the rocks, the team decided to acquire the services of Alex Bregman without first discussing the matter with their established third baseman. Devers wasn't the best defensive player, but he had still provided valuable services to his team and was the one identified as the face of the franchise after Mookie Betts left for Los Angeles.
2025:
– Red Sox sign Alex Bregman without telling Rafael Devers
– Devers gets upset
– Both parties dislike each other
– Red Sox trade Devers
– Red Sox don't extend Bregman2026:
– No Bregman
– No DeversMasterclass plan, Craig Breslow. pic.twitter.com/bnZPGBdBOG
– Jordan Moore (@iJordanMoore) January 11, 2026
As you can imagine, the club's decision to lure Bregman to Boston on the sly made the relationship with Devers untenable, and he wasn't at all keen on the idea of switching positions to make room for the newcomer.
The Red Sox resolved the situation by trading the disgruntled Devers to the San Francisco Giants, and he curiously agreed to play first base shortly after arriving there.
Today, with the signing of Bregman in Chicago, Sox management, led by Craig Breslow, must make its mea culpa for having mishandled the situation and misjudged its chances of retaining Bregman in Boston. By relying on the return of the third cushion player for the next few years, they put all their eggs in one basket and reaped nothing in the process.
It's a far cry from a stroke of genius here, or a home run in baseball parlance. Breslow and his gang got away with it, and a solid one at that.
So the team will likely have to fall back on young Marcelo Mayer to fill the gap left by Bregman's loss at third. Mayer is very good, but lacks experience, having played just 44 games in 2025 with the team. In 136 at-bats, the 23-year-old hit for a .228 average.
A first-round pick in 2021, he's part of the club's future, but he shouldn't have expected to fill such big shoes in his second season in the Majors.
Unless, of course, Breslow decides to trade up and bring more experience to the hot corner. Chaim Bloom must already be salivating at the idea of dealing with Breslow again, this time mentioning the name of Nolan Arenado.
This content was created with the help of AI.