However, one organization was smart about their rebuild, and one has not been. Sure you could say OKC has been lucky in their drafting--there's probably some truth to that. But (and this is key) it's just as easy to say that OKC had a system in place to be smart about who they were drafting, how those players would fit in terms of role on the roster, and a plan moving forward. Everything I've heard about OKC's FO and coaching has been positive and I think that shows in the emergence of that team and the players they drafted.
It would take a REAL homer to think the Blazer organization was anywhere close to that of OKC over the last decade.
Not only is OKC a VASTLY better team, with young (younger?) players on their roster, 
in the next (7) years they have stockpiled (13) 1st round picks (2) swaps & (17) 2nd round picks to go along with their stacked and young roster
POR by comparison, has (8, assuming pick traded to CHI never conveys) 1st round picks, (2) potential swaps and (7) 2nd round picks (assuming pick traded to CHI never conveys). Meaning, in addition to their own picks, 
they have a net of (1) extra 1st round pick and 1 or 2 potential pick swaps), just pathetic for a rebuilding small-market team.
OKC1st round picksBest b\t LAC\HOU
MIA 1-14/27' 2nd
PHI 1-6/1-4/1-4/27' 2nd
UTA 1-10/1-8/nothing
[26']
Gets [2] best b\t OKC\LAC\HOU (1-4)
[27'] OKC
DEN 1-5/1-5/1-5/29' 2nd
Swap rights w\LAC
[28'] OKC
Swap rights w\DAL
[29] OKC 
DEN 1-5/1-5/30' 2nd
[30 & 31] OKC
POR 1st round picks[25'] POR 1-14/1-14/1-14/1-14/28' 2nd
[26']POR same as above
[27']POR same as above
[28']POR same as above
MIL swap - 
void if CHI still holds POR pick[29']
1st/3rd best of POR\BOS\MIL
[30'] POR
MIL swap
[31'] POR
One team [OKC] is run exceptionally well (masterclass), the other team [POR] is run poorly, better than the Olshey years', but that is not a high bar to climb now is it?
But sure, they should keep Simons\Grant\Williams\Thybulle & Ayton, netting little\nothing additional for them (who needs more draft assets anyway?) & they should certainly strive for the playoffs\play in (relinquishing their 25' (heck or even 26') 1st rounder to CHI in what looks to be two incredibly loaded drafts), who needs more talent anyway? and they should certainly play those vets as many minutes as possible this year to negate any positive (low pick\odds) that could come from another dismal\losing year (Flagg\Bailey\Edgecome\Harper are all overrated anyway, right?).
I think some fans are just content to watch their team perpetually run on the hamster wheel.