3. Overpaying Trevor Story
Bloom was notoriously allergic to free agency during his time in Boston, refusing to pursue (much less acquire) the majority of big-ticket free agents that became available. He preferred to swim in the shallow end, as nearly all of his free-agent deals were one or two-year contracts on older or injury-prone veterans. Despite Red Sox fans’ pleas to add some star power, he never went after the Aaron Judges or Justin Verlanders of the world.
When Bloom finally did take a big swing in free agency, he whiffed massively. Towards the end of the 2021-22 offseason, he splurged on shortstop Trevor Story, giving him a six-year, $140 million contract when seemingly every other team had already passed on him.
Two years into the deal, it has not panned out. Story, who was already known to have an elbow issue when he signed with Boston, has missed a ton of time with injuries. And when he has played, his offensive production has been well below league average, especially this season.
With Story on the wrong side of 30 now, the chances of him becoming an All-Star player again look increasingly remote. The Red Sox already have an albatross contract on their payroll in Chris Sale, and Bloom effectively added another one with the Story deal.
Worse, he spent money that could’ve been used to keep a durable, homegrown shortstop who ended up leaving in free agency.