Here's the problem.... I don't think it's entirely on Olshey. I think it's a combination of Paul and whoever he has as GM.
What makes you think that the next guy he hires is going to be any better than Neil or Cho or Patterson or Nash or KP?
I look around the league and see NO as one of the top 5 or 6 GMs, period. The problem is you get rid of him, you have a slim chance of getting someone any better.
No GM is perfect in their drafting ability. Yet we have one of the better backcourt combos in the league. The bigs he's drafted are all 3pt shooters. His 2nd round picks, Crabbe and Connaughton both turned into NBA regular rotation players.
The Nurkic trade was brilliant. He turned mediocrity at the C position into a 23 year old (with a future) who's getting us 14.3 PPG and 8.2 rebounds in ~27 minutes.
NO has made big offers to the top FAs, but they won't come here. That's something any GM here is going to have to deal with.
Signing ET was one of the only ways to get an FA to come here. Target someone just under the top tier and go get him while the other teams pick over the top tier guys.
Judging talent is only half the game as GM these days. The other half is figuring out the puzzle that is a roster within the confines of the CBA. At this latter thing, I don't know anyone can do it better. And it's a HUGE deal.
The Blazers have made the playoffs in each of NO's seasons, starting with season 2.
It's season 3 of the rebuild, and we're on pace to have our best record of the 3. Looks like progress and not stagnation or getting worse.
Guys we've traded for haven't looked as good for us as they have for their other teams. Jamal Crawford is the obvious example. Just because you think we'd be better off on paper if we finagled the CBA to get those players instead of the guys we have doesn't mean we're a better team.
We're currently 5th seed, tied with OKC. OKC's big acquisitions of PG and Melo didn't make them a better team than ours. The grass isn't always greener.