Something that really cannot be argued is that the Sox, currently, are almost certainly either at the peak of their prospect depth / farm system quality right now, or will be between now and next year's offseason, likely depending on what we do in terms of trading between now and then.
We will be:
1) picking lower, in the draft;
2) have less draft pool money;
3) have less INTL money;
4) will pick lower on the waiver wire;
5) pick lower in the Rule-5 order;
6) will be keeping 40-man roster spots open for AAAA/fringe MLBers and "win-now" veterans / bench and pen pieces instead of using them for prospects, so there is less room on the 40-man;
7) we will generally be attempting to trade prospects for vets instead of trading vets for prospects ...
...for probably the next 5+ seasons consecutively.
We ***really*** need to manage our assets best, right now. If we don't, we will probably fuck up both our win-now window and fuck up our ability to transition from the coming win-now period to a Cardinals-like spot-patch contention period after (where we can make adjustments year to year but still play competitive baseball for several years after our extended young guys' contracts end). That transition is important because if we don't manage our assets well now then we will probably be looking at a need to fully rebuild when our Moncada/Robert/Eloy/etc. group gets to the end of their deals, ala the Cubs current situation.
Right now, as I count it, we have Kopech, Crochet, Kelly, and Stiever all IMO as blue chipper SP prospects, regardless of where they are nationally ranked, and Dunning, Thompson, Dalquist, Lambert, and Vera as as very good SP prospects also who very likely have an MLB future and aren't just the kind of fringe guys that we're used to. Vaughn is an elite hitting prospect and the best 1B prospect in baseball, and one of if not the best pure hitting prospect in baseball. Then there is still maybe some life in other areas, like perhaps Collins, Rutherford, Burger, etc. We still have a good system that may actually be a bit underrated ATM. Let's not just piss it away. In all likelihood if we manage it very well it will gradually diminish to a bottom third system over the next 2 or 3 years, and after that, it will really be a struggle to keep it on the high side of the bottom third instead of the middle or lower portion of the bottom third.