Chaim Bloom's trades with Boston Red Sox are about fit not familiarity

Since the 2025 MLB trade deadline, the St. Louis Cardinals have made four trades with the Boston Red Sox. Making four trades with one team isn't unique, but it is noteworthy. It's even more noteworthy when that team is the current president of baseball operations' prior employer.

Prior to the 2020 season, the Boston Red Sox hired Chaim Bloom, a young analytical executive from the Tampa Bay Rays, to be their Chief Baseball Officer. Bloom, only 36 at the time, was tasked with lowering Boston's payroll while still building a competitor year in and year out. Boston touted baseball's highest payroll in 2019 while Tampa had baseball's lowest payroll, and the two teams couldn't have finished further from each other in the standings.

Bloom spent four years in Boston before coming to the St. Louis Cardinals as an advisor to president of baseball operations John Mozeliak. In his role as advisor, Bloom would vet the minor league teams and provide advice to Mozeliak. The assumption at the time of his hiring was that he would supplant Mozeliak as POBO down the road.

Chaim Bloom did just that, officially becoming the Cardinals' president of baseball operations after the 2025 season.

His offseason has been busy so far, as he's made three transactions in just two months. Chaim Bloom has already traded starting pitcher Sonny Gray and first baseman Willson Contreras. He's also signed starting pitcher Dustin May. Ironically, all three of these deals involved the Boston Red Sox, Bloom's former team.

Chaim Bloom's moves with the Boston Red Sox are not a sign of him favoring his old team.

Let's go back to the 2025 trade deadline. The Cardinals traded swingman Steven Matz to the Red Sox for first baseman Blaze Jordan. While Bloom wasn't in charge at the time, he was still helping Mozeliak make decisions.

This offseason, the Cardinals have traded both Sonny Gray and Willson Contreras to the Red Sox. In return, they received a plethora of pitchers — Brandon Clarke, Richard Fitts, Hunter Dobbins and Yhoiker Fajardo and Blake Aita. Bloom also signed free agent starter Dustin May, who most recently pitched for the Boston Red Sox in the second half of the 2025 season.

For those keeping score at home, that is seven players whom the Cardinals have brought over from Boston in the last six months. Given the circumstances of leadership in St. Louis, several fans have begun wondering if Chaim Bloom can make any trades with another team.

Of the seven players the Cardinals have acquired since the trade deadline, only two have connections to Chaim Bloom. Blaze Jordan was drafted in 2020, Bloom's first draft with the Red Sox, and Hunter Dobbins was drafted in 2021. The remaining players — May, Clarke, Fitts, Fajardo, and Aita — all came to Boston after Chaim Bloom left the team.

Bloom striking deals with Boston is likely more due to fit than familiarity. The Red Sox were in need of a starting pitcher and a first baseman this offseason, and the Cardinals were able to fill both of those needs for Boston. The Cardinals, meanwhile, have their eyes set on the future. Given Boston's talented and deep farm system, they were a logical partner for the Cardinals.

There's a strong possibility that Chaim has remained in contact with folks from Boston, given his time spent there. That is the extent of his "favoritism" with Boston.

The Cardinals still have several potential trades left this offseason. Nolan Arenado, JoJo Romero, and Brendan Donovan remain Cardinals. There's a chance Bloom dips back into Boston's farm system with one of these players, but there's probably a greater chance he starts making trades elsewhere. We'll just have to wait and see if he truly misses Boston's farm system.