2. Letting Xander Bogaerts Walk
If Boston still had Dave Dombrowski (or literally anyone else) running the show last winter, there’s a good chance Bogaerts would still be with the Red Sox.
Instead, he’s with the Padres now for what will likely be the rest of his career after Bloom severely botched his contract situation.
Heading into the 2022 season, it was common knowledge that Bogaerts planned to opt out of his contract and test free agency. That gave Bloom a full year to figure out what to do with Bogaerts, and he absolutely squandered it.
Bogaerts was apparently looking for the type of deal Story got — a five or six-year contract in the neighborhood of $150 or $160 million. Instead, Bloom lowballed him with four years and $90 million — well below the market rate for an All-Star shortstop.
Naturally, Bogaerts rejected this insultingly low offer and went to free agency, where he landed a massive 11-year, $275 million megadeal from the Padres — three times Bloom’s initial offer.
Bloom had the chance to extend Bogaerts and blew it. He had the chance to trade Bogaerts and blew it. Instead, he lost one of the best shortstops in franchise history for nothing.