Chaim Bloom Looks Back On Unpopular Mookie Betts Trade With Red Sox

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 time hasn’t exactly been kind to it since then. Bloom knows how the optics of the deal look, and when looking back on the trade, he admitted that while he didn’t want to trade Betts, the position the team was in made it feel like a necessity for him.

“It’s never fun to take a player of that caliber in the prime of his career — that I had seen right in my face as an opponent for so many years with the Rays, then be on the same side as him very briefly — and end up moving him,” Bloom said of the Betts trade.

“Obviously, there was a bigger picture than that deal. That deal wasn’t about the valuation of the talent. It was just about where the organization was.”

With Bloom struggling to build Boston into a contender, he ended up getting fired late in the 2023 campaign. While the Sox are now reaping some of the rewards of Bloom’s work with the farm system, he remains an unpopular figure in Boston.

There’s no doubt the Betts trade has backfired on the Red Sox, but the team is finally in a position to build a winner once again. How they operate over the coming months will ultimately determine how successful they are in the 2026 season and beyond.