Most of those Yankee trade examples you gave were from 2017 or earlier. The market for prospects collapsed in 2018 and 2019...as did the value of veterans like Smoak, Pillar, etc. The returns we've gotten over the past 2 years are very similar to other deals in baseball. That exacerbates your issue re: timing; however, if their hands were in fact tied by Ownership, then that muddies the waters. I don't think anyone thought the market would go from Quintana for Eloy down to Gray for the 3 marginal guys the Yankees gave up to get him. BTW - Gray gives you a good example of how much the market collapse as even the GREAT Cashman traded Gray for next to nothing. The collapse of the market has caught almost all of MLB by surprise. The White Sox have to be viewed as brilliant as they managed to unload Quintana and Easton for massive hauls right before it happened. Cashman stole Torres too right before it collapsed.
Who knows when the FO got approval to tear down this team. Maybe they had the ability the whole time, maybe Rogers stopped them until this year. Tough to judge without that information. At least in the meantime, they were able to create payroll flexibility, while building depth within the farm system.