For the two franchises that combined for 10 world championships and 20 conference championship games/series appearances over a 20-year period, how long will it be before one of them tastes playoff glory again?
Right now, Boston is the first team on the outside looking in, with Tampa Bay, Houston and Toronto owning the three wild card slots at the moment. But right behind the Sox lurks Shohei Ohtani and the Angels, with the Yankees and Mariners still in striking position.
With no clue how this year's deadline is going to turn out, let's take a look back through the years at some of the best and worst deadline dealings in Red Sox history.
What's their ceiling in 2023? Has the recent winning changed your mind on what this team is capable of? Or are you still concerned and waiting for another shoe to drop?