Oftentimes, in an MLB offseason, there are multiple “winners” and “losers.” Usually, whether your team “won” or “lost,” its offseason is based on the front office's activity or lack thereof. Teams make noteworthy trades or sign big-name players to bolster their lineup or pitching rotation — or they don’t.

For the past two seasons the Boston Red Sox have found themselves in the cellar of the American League East with records of 71-91 and 78-84, respectively. Then, on Aug. 19, owner John Henry and company...