I agree it is a poopoo trade regardless based on risk/reward and awful and panicked negotiating tactics. But to play along with your hypothetical if it turns out to be Buddy, the #2 and #4 in 2017 draft vs. paying Boogie $209M and losing our pick to CHI (which would've happened if we kept him), then it turns into a good trade. Not because of judgment but amazing luck. I say that not trusting Vlade as a drafter either. But the draft is so strong, it will be hard to mess it up. He doesn't have to be brilliant to get it right or semi-right.
As an aside and as a lot of us speculated
Vlade said in Bee interview the 2017 #1 and 2019 #1 was on the table from NOP, then pulled when Dan Fegan meddled. If this was the haul with no protection, there would have been less backlash, though still not a great deal. He also said if his decision does not work out he will step down in two years. This is interesting because it implies (1) the decision was his and his alone and (2) he will last that long in current capacity to see how this plays out.