The Boston Red Sox are on the rise, and after finding their way to the playoffs in 2025, they are expected to be busy over the offseason. One guy who is watching the Red Sox’s return to glory from afar is their former chief baseball officer, Chaim Bloom .

Now with the St. Louis Cardinals as their president of baseball operations, Bloom spent four seasons running Boston’s front office. For the most part, Bloom focused on revamping the team’s farm system, which often came at the cost of sacrificing major league talent.

The most noteworthy of Bloom’s moves saw him trade Mookie Betts to the Los Angeles Dodgers shortly after being hired. Since the deal, Betts has gone on to win three World Series championships with the Dodgers.

The trade was immediately unpopular among Red Sox fans, and

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