Craig Breslow was one of the most active players on the trade market this past offseason, which allowed Boston Red Sox fans to notice a pattern that was already slightly evident. He has a habit of trading with the same teams multiple times.
It started with the Pittsburgh Pirates, headed by former Red Sox executive, Ben Cherington. The Sox and the Buccos have made multiple minor league transactions since Breslow took over as CBO, and Quinn Priester (now a Milwaukee Brewer) and Johan Oviedo both came to Boston from the Pirates organization. Now, Chaim Bloom, another former Red Sox exec, seems to have taken over as the primary trade partner.
Many Red Sox fans thought they were noticing a "bromance," of sorts between Breslow and Bloom, as the frequency of the trades between the Red Sox and St. Louis Cardinals can't be a coincidence. Breslow told Jen McCaffrey of The Athletic that he and Bloom have unique relationship outside of the big leagues because their sons play in the same little league (subscription required).
“We have a great relationship, and we obviously have had very similar experiences, and so, it does make for interesting conversations,” Breslow said. “And yeah, at games, we’ll have to find ways to kind of peel off behind the fence or something to make sure nobody overheard these St. Louis and Boston discussions.”
Craig Breslow and Chaim Bloom's friendship outside of the big leagues could lead to more Red Sox-Cardinals trades
Bloom and Breslow's trading history goes back to the 2025 trade deadline, when they swapped top Red Sox prospect Blaze Jordan for Cards reliever Steven Matz (which is Breslow's best trade deadline move to date). Sonny Gray and Willson Contreras are also former Cardinals, and Richard Fitts and Hunter Dobbins were the prizes of St. Louis' return packages.
The Cardinals are in a similar place that the Red Sox were in before the 2020 season, when they hired Bloom to rebuild their roster and farm system. St. Louis was a perennial playoff contender throughout the 2000s and 2010s, but it's fallen off in recent years — the Cardinals haven't made the playoffs since 2022 and haven't advanced past the Wild Card since 2019.
The Red Sox are seemingly vehemently opposed to paying top dollar for free agents, as evidenced by Breslow's insistence on sticking to the trade market. As long as the Cardinals have veterans that no longer suit them and the Red Sox have more prospects than they have room in the major leagues, fans could see more trades between Bloom and Breslow, two dads who chat at little league games.