The St. Louis Cardinals are in the middle of a top-to-bottom organizational rebuild that has already seen starting pitcher Sonny Gray and All-Star closer Ryan Helsley traded within the last calendar year.

The Cardinals could end up moving more notable players before 2025 ends. Overseeing that rebuild is president of baseball operations Chaim Bloom, who was hired in 2024 after a three-year stint with the Boston Red Sox.

While Bloom was with the Red Sox, he pulled off one of the most infamous trades in the history of the franchise just four months into his tenure.

Bloom traded one-time American League MVP winner and the best player on Boston, Mookie Betts, to the Los Angeles Dodgers. The trade came after contract negotiations stalled between Betts and the Red Sox.

The deal netted Boston Alex Verdugo, Connor Wong and Jeter Downs. Of the two players, Wong is the only one still with the organization. Since the trade, the Dodgers and Betts have won the World Series three times and the Red Sox has made the playoffs twice. Those postseason results were an American League Championship Series loss against the Houston Astros in 2021 and a wild card series loss against the New York Yankees this past season.

In a recent appearance on the Foul Territory podcast, Bloom was asked about the Betts trade and had a hilarious aside where his own family criticized him for the move, while also chalking it up to a difficult decision.

"You have to do what you have to do," Bloom said on the podcast. "It's actually funny. My boys love baseball. And now that they're old enough they really follow this very closely. They're way worse than anyone in the media in terms of how hard they are on me. And they were young enough when (the Betts trade) happened that they weren't really aware of it. Now, my oldest, who's just realized last year that I traded Mookie Betts, he's like 'Dad, what are you doing?' ... Again, sometimes there are hard decisions you have to make in the here and now. If you're not ready to make those, then this is not the business for you. There's also a lot of really good things happening in the organization that are energizing every day in terms of taking our young players, getting the most of it. ... Player development should never stop, even in the big leagues, even with veterans. If there's anything the last five, 10 years in this game should teach us, it's that they're always pathways to improvement for any player, any team, any organization. It is awesome to get a chance to wake up and say 'How can we get better today?'"

Bloom could have to make another difficult decision in the near future.

All-Star second baseman Brendan Donovan, who is under team control through 2027, has been one of the sought-after players in the trade market. According to a report from Katie Woo of the Athletic, the Seattle Mariners and San Francisco Giants have emerged as the front runners to land Donovan.

Woo's report said St. Louis is looking to land "multiple top prospects" for Donovan but it's also been reported by several outlets the organization has already walked back its initial asking price.

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