The Sox are in a very difficult situation, in paper they should be better, they should be fighting with the Yankees for the division instead they are just trying to stay alive in the WC race. A lot of season still left and a lot of things can change.
As somebody explained before, the difference between the 2016 Yanks and the 2019 Sox is that the Yankees were loaded in the upper & mid levels of the minors (Sanchez, Judge, Severino, Bird?!, Montomery, Andujar, etc.) and they were able to take advantage of an unusual trade deadline urgency for the type of players (Chapman, Miller, Beltran, McCann, etc) the Yankees wanted to trade, in the first two they got a ton of good prospects, some keepers and others pieces for different trades.
The Sox upper levels of the minors don't have much, so the issue here is: blow the thing open and sell every useful player they have to retool the farm and contend in 2 or 3 years, or simply keep selling what is left in the farm and plug holes with money, as the Yankees did for so many years.
BTW, I don't understand the hate for Benintendi, he's an above average ballplayer he was a force last year and is young enough to get better, he's just not the superstar some people thought he was, if the Sox trade him they will regret it; also with Betts, the guy is an all-star, not in Trout level (nobody is), he probably won't be worth the money he will demand, but those are homegrown players, which should get the benefit of the doubt. I hope this doesn't happen with Devers.