I remember when sox fans were sure that any "athlete" drafted was a bad idea and any high schooler would fail on the sox because the 3 they drafted over a decade failed. Now Colson Montgomery is our first home grown top 50 prospect since seemingly forever (we have had prospects we've selected in top 5 that were immediately top 50 guys, but few that grew into that position, and you can include Robert but he did cost $60 million and had extensive experience in a pro league).
The problem isn't that hitters explode on the sox. It's that the sox are bad at scouting, and continuously get excited that a previously great hitter is suddenly in their price range. And then it turns out its because they were showing signs of decline, which scared other teams, but sox have terrible scouting so we then say "oh no, don't get this good player, they'll be bad on our team" when they are still younger and more expensive.
Basically - these are all the reasons why I'm certain we'll end up with JD Martinez or Nelson Cruz.