The Chaim Bloom era of the Boston Red Sox was not a fruitful one, as the Red Sox only made the playoffs once between 2019-23, failing to recapture the magic of that 2018 campaign.
Under Bloom's watch, the team focused on tightening the purse strings, and they let face of the franchise Xander Bogaerts leave in free agency once he received a huge offer from the San Diego Padres.
That was probably a smart move in hindsight, although it certainly wasn't a popular one. And while Bloom's fingerprints are all over the current roster, the team went just 267-262 under his watch.
However, nothing βΒ and I mean nothing β will define Bloom's tenure in Boston more than the infamous Mookie Betts trade. In exchange for their MVP-winning superstar, the Red Sox received outfielder Alex Verdugo and top prospects Jeter Downs and Connor Wong, as well as some salary relief (the Los Angeles Dodgers took on David Price's contract).
That deal hasn't just flopped β it's arguably the worst MLB trade of the last decade, if not longer.
Now running the St. Louis Cardinals, Bloom is distanced enough from the deal to appreciate that the tough call he made was probably the wrong one. At least according to his kids.
"He's like, Dad, WHAT are you doing?" π
β Foul Territory (@FoulTerritoryTV) December 14, 2025
Chaim Bloom's kids are finally old enough to realize that he traded Mookie Betts. pic.twitter.com/286TUmmqRS
Ownership, not Chaim Bloom, is to blame for Red Sox's Mookie Betts debacle
This has been an ongoing conversation for the last five-plus years, and yes, Bloom is the guy who ultimately pulled the trigger on the deal. The return he got for Betts, at the time a top-five player in the sport, was simply unacceptable.
But while the front office executive became the fall guy, the lion's share of the blame falls on owners John Henry and Tom Werner. They were the ones who didn't want to pay a third straight year of luxury tax penalties after approving Dave Dombrowski's reckless spending, and they were the ones who hired Bloom with the mandate of cutting about $30 million from the team's payroll.
Was trading Betts the best way to achieve that goal? Probably not, but he was heading into his final year of team control via arbitration and was demanding a record-setting extension. The Red Sox should have been the ones to pay that, not the Dodgers. Surely, if Bloom had enough money at his disposal, he would have extended Betts on a similar contract to what he ultimately got in Los Angeles.
Maybe this is all revisionist history. Perhaps Bloom did accept the Red Sox job with the intention of trading an in-his-prime MVP and champion. He certainly accepts his part in making the deal come to fruition.
But perhaps he should introduce his kids to Henry and Werner. That'd be a conversation worth listening to.
