We need to stop evaluating trades based on how the players careers end up.
If we traded Mark Stone for three firsts and none panned out, would that have been a bad trade? If we had traded him for a 2021 7th rounder that turned into a hall-of-famer, would that have been a good trade?
Excellent point. When picks are involved, especially the centerpiece, the trade value ends once the pick is given. Barring a top 5 first round pick or something where there's consensus on who goes where.
In the infinite vastness of the multiverse, there are other realities where the original picks GM picks the same player... But it's probably not our reality. That probability only goes down the further down the draft pick is.
So you have to fall back on the relative value of the pieces in the moment. There's value and insight to be gained in analysing players careers and how moves panned out, of course, but it's different information.
Zibby is a good example. A lot of people revise that trade because of how his career developed outside of Ottawa. Like there's some inherent guarantee that he would have become what he is here... Nurture has as much a part to play in our development as nature does. Lots of guys have all the talent in the world and never figure it out for one reason or another. Life works the other way too.