1. Trading Mookie Betts
All of the mistakes we’ve covered, this one was by far the worst.
When Bloom took over the Red Sox in late 2019, he inherited a roster with one of the best players in baseball. At the time, Mookie Betts was widely regarded as the second-best player in the game, behind only Mike Trout. He was already one of the best players in team history and was building a case as a future first-ballot Hall of Famer.
Little more than three months later, Bloom traded him to the Dodgers along with David Price. In return, Bloom received outfielder Alex Verdugo and two prospects — infielder Jeter Downs and catcher Connor Wong.
Three and a half years since the trade, it is considered one of the worst trades in MLB history. Not just Red Sox history, but in the entire history of the sport, going back to when Boston infamously sold Babe Ruth to the Yankees.
Rather than extend Betts (who was one year away from free agency) or sign him the following winter, Bloom traded away a 27-year-old MVP in the heart of his prime rather than pay him what he was worth.
That was bad enough, but Bloom’s return was exceptionally poor. Verdugo has been a league-average outfielder nowhere close to Betts’ caliber, Wong has emerged as a decent catcher, and Downs barely played for the Sox before being DFA’ed as a failed prospect.
The fact that Bloom did not acquire any pitching for Betts — which Boston desperately needed at the time (and still needs) — or any of LA’s highly coveted prospects was a major miss on his part.
Bloom should have never traded Betts in the first place, regardless of what ownership may or may not have told him to do. And if he did, he needed to get much more in return. He failed on both fronts, setting the franchise back years in the process.
You have to give Bloom credit — he was truly great at losing homegrown talent, and that’s why he ultimately lost his job.