Welcome back to Smash Or Pass, our offseason series in which we examine various free agents and trade targets to determine whether they make sense for the Red Sox. Next up, a riddle, wrapped in an enigma, playing for the worst team of all-time.
Rooting for the White Sox is maybe the worst deal in baseball history. I’m sure fans of the now-Guardians may disagree, but subtract the 2005 title and it’s not merely that the White Sox didn’t win a title since 1919; it’s that they may as well have not existed.