The Sox are positioned right now that could make some sort of "make or break" move to improve the 2021 season and try for post-season contention. And if they are out of it at the deadline, they have enough short term deals that can still do a mini fire sale and get some prospects/young major leaguers and be poised for 2022.
Right now, they have the following players in their final year aka deadline trade bait: Rodriguez, Barnes, Ottavino, and Richards And then they have the additional year for Benintendi, Andriese, Eovaldi and Plawecki. Even in the biggest deadline fire sales, how many deals an one team make? If they only move the one year players, that's four trades at one deadline, which is an awful lot for any team to make in that time frame anyway.