You seem to be yearning for a new FO that will pitch the owners on signing those big deals again, but look at the list you made:
Crawford (bottom of the barrel terrible)
Gonzalez (meh to bad)
Hanley (bad)
Sandoval (in competition with Crawford)
Price (WS aside, bad)
JD (good)
Sale (terrible so far)
Why are we trying to get back to that?
Fair, and a couple of reasons:
1 - Each of the GMs that inked those deals had won a(t least one world series), so I trust them more. What can I say. I'm a sucker for a World Series title giving some cachet.
2- Because I think there is a large difference between betting on a 26 year old whom has shown an ability to produce in Boston as opposed to Crawford (29), Gonzalez (29), Ramirez (31), Sandoval (28), Price (30), JD Martinez (30) whom hadn't.
2a - Sale, started to show signs of breaking down in 2018 when he missed 5 (or 6) turns through the rotation and was then pretty awful in the playoffs. He was going to be 30 when the extension started and doesn't have a body type or delivery that one would bank on. That said, I liked the Price singing (not the Sale extension) so call those a "wash", if you will.
3 - Because I think you need core pieces, the only one we have is Trevor Story and I'd like Devers to be a second. To my point above, I think you need top of the roster talent to win a world series. Sure, the Royals managed without any in 2014. But the Rays / As model has gotten beat in the playoffs before raising a flag each time. To reiterate, though it happened once (KC) I think it's
almost impossible to win a World Series without high end roster talent, and the only one we have right now that is even a moderately safe bet to play a full season effectively is Trevor Story.
4 - This in conjecture, but I don't think Boston is seen in a positive light at all right now by young MLB players or the industry in general, and I'd like to change that.