Sexton and Olynyk would be the natural filler salary going out in a potential Lilard trade. Hendricks + 3 first roundt picks of Portland`s choosing would in my opinion be the least Portland would expect. We would ahve to send a million or two extra in salaries to get to the $36 million we need to make the trade legal, but that is not a problem.
The natural follow up trade would be THT, Keyonte George & 2 first round picks for OG Anunoby. That would leave us with this line-up:
Lilard, Clarkson, Dunn
Clarkson, Agbaji
Lauri, Fontecchio, Sensebaugh
Collins, - Lauri - Sensebaugh
Kessler, Collins
If accepted, these deals would give us both a very competitive team and a few picks left to build further. But, we will have to give up a lot and I am not sure how good this team would be. Best case scenario, we get home court advantage and are competitive in the play offs. Worst case scenario is having a season like Minnesota did last year and OG leaving as a free agent next summer.