I'm thinking a little differently.
It's probably true that Portland won't use both draft picks, even though the 23rd pick would offer the Blazers a low-cost player for 4 years. The best use of that pick may be to use it to leverage the Bulls and end the stupid obligation against all future Blazers first's
but I am not expecting any big move. Not because Cronin isn't looking for one; but because I suspect he's running up against the same wall he has already run up against. That being the rest of the NBA doesn't value Portland's assets high enough to offer a good trade. I think the Blazers only have 3 assets with any significant positive value: Dame, Sharpe, and their pick. For the rest it's neutral or negative value
and my guess is that Cronin has been communicating that to Dame