The tricky thing for Portland is they have to find a team who has a player good enough to give up the #3 pick for who is already in their prime and ready to help Lillard win and that team also has to want to rebuild/reset with a #3 pick. Maybe Toronto punts on Pascal Siakam since he's going to cost a fortune to retain and they build around Scottie Barnes, OG Anunoby, and whoever they can pick at #3, #13, and #23? Maybe New Orleans will give up Brandon Ingram now that they have Herb Jones and try to build around a Scoot Henderson and Zion Williamson duo? There's not a lot of teams that potentially fit both criteria. Regardless, Portland is going to want to keep Nurkic and Simons if they're fully committed to being competitive so they're going to need help from a third team to get the salaries to match.