This is what's troubling about having the current Sox front office, Jerry included, oversee this rebuild.
The Sox had a great core of Thomas, Ordonez, Lee, Konerko, Durham and couldn't build a winner around them. If only they would have ponied up for another decent starting pitcher in those years (2000 -2004) instead of going without a competent 5th starter and cutting salary by dumping guys like Durham and Lofton for basically nothing.
In 2005, everything just came together, despite losing Ordonez, thanks to bringing in guys like AJ, Iguchi, and catching lightning in a bottle with the bullpen, so kudos to KW for that. But despite it looking like the Sox were about to start a dynasty, they only made the playoffs once after that in 2008, barely getting in and then being eliminated in the first round.
Then the Sox had another good young core with guys like Sale, Quintana, Eaton, etc. but failed to build a winner around them either, instead surrounding them with washed up vets and B-level free agents.
Now they had the fans suffer through this rebuild to acquire another promising young core. But if they once again fail to augment this core with top tier talent instead of half-assing it as usual, we will just be back where we started, maybe making the playoffs once in the next several years and not going very deep.
Here's hoping this time Jerry opens his wallet for top tier free agents and Hahn & Co. do a better job of identifying talent to bring in. But don't hold your breath. I'd feel much better about this rebuild with other people in charge.