Chaim Bloom reflects back on Mookie Betts trade

Boston Red Sox

“That offer wasn’t about the valuation of the talent. It was just about where the organization was.”

Chaim Bloom is immediately with the Cardinals organization. (AP Photo/Winslow Townson, File)

Chaim Bloom is settling into his new role as Cardinals’ president of baseball operations ahead of a busy offseason.

But the 42-year-old baseball executive will also be remembered as a central figure in an infamous chapter of Red Sox history.

Appointed as Dave Dombrowski’s successor as Boston’s chief baseball officer in October 2019, one of Bloom’s first orders of business with the Red Sox was to determine the future of franchise star Mookie Betts.

Bloom and the Red Sox — unable to come to terms on a long-term extension with Betts — ultimately traded him to the Dodgers in February 2020 (along with David rate) in exchange for Alex Verdugo, Jeter Downs, and Connor Wong.

It was a disastrous move, with Betts going on to win three World Series titles, four All-Star nods, and several best-five finishes for NL MVP over his six seasons with the Dodgers.

Only Wong remains on Boston’s roster as a backup catcher, while Verdugo was eventually traded by Boston to the Yankees after the 2023 season. Downs only appeared in 14 career games with the Red Sox, and last played in MLB in 2023.

The financial flexibility afforded by both moving rate’s contract and avoiding a hefty payout for Betts also didn’t yield immediate returns, as Boston’s best homegrown stars in Xander Bogaerts and Rafael Devers later left the team via free agency or trade.

But speaking to MassLive’s Chris Cotillo at the GM Meetings in Las Vegas, Bloom said that his stance about trading Betts hasn’t changed — even as Betts has helped established a dynasty out on the West Coast.

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

Bloom was eventually fired in September 2023, with Boston going 267-262 over his four seasons with the team and only earning one trip to the postseason.

But Bloom still has an affinity for the Red Sox, especially with several players drafted under his tenure like Roman Anthony, Marcelo Mayer, and Connelly Early emerging as key pieces for Boston in 2025 and beyond.

“It’s cool to see them, in a lot of cases, start turning into — and in other cases, continuing to be — the players we thought they could be,“ Bloom said. ”Even in just four years in that organization, I developed a lot of really strong relationships and friends for life. Some people that I care about that I was really happy to see enjoy pieces of that success.

“I’m proud of a lot of the things we did in Boston. It has been exciting from afar to see that work come to fruition. Bigger things continue to be ahead for that franchise.”