I really don’t blame Olshey for the trajectory part. The blame there goes to this guy:
The short story is that Dame kept the Blazers from getting into lottery territory after Aldridge left. Olshey hasn’t had a top pick to work with since drafting Dame. As a small market, it’s absolutely essential to get two really good players through the draft to build around, and one of them has to be a big. Look at Phoenix, Denver and Utah. All three were able to draft talent at the PG spot and center. Having those core pieces on rookie deals let’s a GM fill in around them with other solid pieces and then have room to grab a vet like Conley or Paul. Olshey did his best to solve that issue by trading for Nurk and moving up to draft Collins with a 10th pick. Neither one has been able to stay healthy enough to really deliver for the team yet.
So yeah, it’s all Dame’s fault.