This thought has always crossed my mind, and I saw another poster talking about it recently.
The White Sox are known to be a stingy organization. The idea of the rebuild was acquire cheap, young talent through draft picks and trades. That talent gets supplemented with established players who will cost more. In typical rebuilds, you trade your high end players for a bunch of high end prospects (Sale, Quitana, Eaton, etc.). As far as established veterans who have been traded, these guys had just about the best contracts out there. Cheap and under control for a while.
Trading a player like Yoan would result in an unprecedented return. You could absolutely stack the system and once again have one of the best, WHILE being loaded with young talent in the majors. Now, I'm not advocating trading Yoan, but the 2nd generation rebuild might be the true way to develop a multiple championship dynasty. Interesting to think about.