The Boston Red Sox, mired very deep in the American League East cellar, are providing a rather firm data point in favor of the reality behind Murphy's Law; what could go wrong this season almost certainly has gone wrong for the 2025 playoff participants.
There's not much need to do an autopsy exploring the "why" behind this underperformance. Injuries to stars like Garrett Crochet and Roman Anthony, disappointing encores from 2025 standouts like Brayan Bello and Carlos Narváez, and an offense that often seems allergic to hitting are a good summation behind the team's very-far-below-.500 record this year.
Naturally, that's put chief baseball officer Craig Breslow on the hot seat, seeing as a great many of the deals he's made have yet to pan out in his favor. Everything from trade acquisitions (e.g., Caleb Durbin), to free agents (e.g., Danny Coulombe) and even moves that didn't happen (e.g., re-signing Alex Bregman) have seemingly worked against the Red Sox this season.
Would it help if, after all that, I told you all how well the organization's most recent front-office executives were performing in 2026?
Current NL Wild Card pic.twitter.com/QKUsFO0KGc
— Stats (@redsoxstats) June 17, 2026
Red Sox's past executives are dancing circles around Craig Breslow in 2026
Dave Dombrowski's success in Philadelphia is the least novel and least surprising of the bunch. After being ousted from Boston following the 2019 season, the win-now-at-all-costs maven took over the Phillies and subsequently guided them to the 2022 World Series and a pair of National League East titles. He's put together a very old and very expensive roster there (what else is new?), but Dombrowski's teams remain unassailably competitive year in and year out.
On the other hand, seeing Paul Toboni (Washington Nationals) and Chaim Bloom (St. Louis Cardinals) in such strong positions in supposed "rebuilding years" is a bit of a slap in the face. The former, long viewed as Breslow's successor if things didn't work out, took over a team that hadn't won more than 71 games since winning the World Series in 2019 and now fields the highest-scoring offense in the league. Offseason additions made by Toboni like Curtis Mead and Foster Griffin have played a huge part in the organization's turnaround.
Meanwhile, Bloom has continuously reminded us all of his presence in St. Louis with repeated trades featuring Breslow. The Cardinals are now arguably the best story in the league, having dumped their high-priced veterans primarily on the Red Sox and instead featuring a youth movement taking the NL Central by storm.
Oh, and just to rub a little more salt in the wound: One of the teams primarily jostling with the Nationals for the final Wild Card spot, the Chicago Cubs, was Breslow's old stomping grounds. As difficult as this year has been in a vacuum, it becomes almost impossible to explain when looking at the league-wide picture.
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