Were I Portland, I'd blow up my backcourt.
Easy money is on dealing McCollum. He's a scorer who can get tough buckets consistently and should be better if given a more ball-dominant role. Dealing him (eventually) to Minnesota for Covington and Dieng (who Portland could actually use) would be a smart use of resources.
But the more daring move is to deal Lillard for a monster return.
I wonder if Phoenix, for example, would be okay with a deal centered on Ayton and Oubre? They may have to add a pick and an expiring deal to make it work.
They could talk to OKC about their four million draft picks, but none of them are going to be high enough, IMO. A Lillard for Simmons deal (with extras, obviously) may not work, but it's fun to think about in a vacuum.
Lillard for Cleveland's unprotected number one and Kevin Love would also be a fascinating hypothetical.