The Boston Red Sox were well acquainted with Chaim Bloom before Craig Breslow made three trades with him since the second half of the 2025 season. The former Red Sox chief baseball officer has taken the helm of the St. Louis Cardinals organization to oversee a massive rebuild, like he did in Boston.

And rebuild he has. Bloom has traded multiple expensive and/or long-term contracts this offseason, including Sonny Gray and Willson Contreras to the Red Sox. After those trades, he shipped Nolan Arenado to the Arizona Diamondbacks and Brendan Donovan to the Seattle Mariners.

The Red Sox also underwent a sort-of rebuild under Bloom. He orchestrated the trade of Mookie Betts and Xander Bogaerts walked during his tenure. Weeks after Breslow took over as CBO, the entire 2018 World Series-winning team (besides Rafael Devers), the winningest club in Red Sox history, was gone.

Bloom was hired to cut Boston’s payroll and revamp its farm system, which is exactly what he did — all of the risky, ugly moves he made were at the direction of team ownership, and he took the fall for them when he was fired two weeks before the 2023 season ended. The Red Sox only made the playoffs one time during Bloom’s four-year tenure as CBO because they didn’t need a rebuild.

Chaim Bloom is a much better fit with the Cardinals than he ever was with the Red Sox

Chaim Bloom is going in the proper direction with the Cardinals, says @Ken_Rosenthal.

"This is what they need to do, at this moment in time, in their evolution as an organization." pic.twitter.com/kgrfyLgoKN

— Foul Territory (@FoulTerritoryTV) February 3, 2026

Chaim Bloom is going in the proper direction with the Cardinals, says @Ken_Rosenthal.

Bloom’s skillset is much more suited to the Cardinals’ needs than he ever was to Boston’s. The Cardinals have the second most World Series wins in MLB (behind you-know-who) and they made the World Series four times from 2001-13, losing to the Red Sox in two of those series. Since 2016, they’ve made the playoffs four times and lost in the Wild Card three times.

Unlike the Red Sox when Bloom took over, St. Louis actually needs a change of pace. Its many long-term contracts haven’t panned out — Arenado has regressed at the plate, Contreras couldn’t stick behind the plate and Gray represents a $21 million CBT hit at 36 years old. Keeping that much money on a roster that needs as much work as St. Louis’ does is an unwise investment. Meanwhile, the 2018 Red Sox were a team on the rise, purposely disassembled to save money.

Bloom did the job he was hired to do with the Red Sox, although he didn’t have to neglect the big league roster to bolster the farm system: that direction was given to him from higher-ups. Many of his high-profile draft picks have ascended to the major leagues, and Roman Anthony, Marcelo Mayer and even Kristian Campbell could grow into franchise staples.

Boston fans, at large, only understood the direction Bloom was given when Breslow took over and started doing very similar things. The Cardinals, on the other hand, actually need to rebuild, making Bloom a much better fit for their needs and explaining his rocky tenure with the Red Sox.