There really was no way for Olshey to bring back the WCF team, all of Curry, Hood, Kanter were free agents. Blazers actually did the best they could to bring back the one with two way starter upside in Hood IMO, it just didn't work out.
Trading both Aminu and Harkless seemed bad to me, thought we should have kept 1.
But really that WCF roster starters were pretty flawed and just had a lot of lucky breaks to get as far as they did. Minor tweaks to that roster wouldn't have ever been a good solution.
The 2016 free agent debacle was by far the worst set of moves Olshey did, followed by the Collins draft, with the Roco/Nance picks lost being up there too (and still hitting us until 2028!)
Although I seriously question how much of these moves had Cronin engineering them with how similar the Blazers stupidity continues to this day.