Here's my best "realistic" plan.
POR Gets: Pascal Siakam
PHI Gets: C.J. McCollum, Chris Boucher (absorbed w/ Horford TPE)
TOR Gets: Ben Simmons, 2022 POR 1st
I love that trade package for all teams involved.
Next, have Dame recruit Jerami Grant hard during the Olympics. If he is open to going to Portland, we could get him at a decent value due to his rapport with Detroit.
POR Gets: Jerami Grant, Mason Plumlee
DET Gets: Derrick Jones Jr, Tristan Thompson, Aaron Nesmith, 2024 POR 1st, 2027 POR 1st, 45th Pick (BOS), 2022 BOS 2nd, 2024 BOS 2nd
BOS Gets: Robert Covington
Then sign Nic Batum for the MLE
Before Siakam returns from injury:
Lillard (36) / Simons (12)
Powell (30) / Simons (18)
Little (28) / Batum (17) / Powell (3)
Grant (35) / Batum (13)
Nurkic (28) / Plumlee (20)
After Siakam returns from injury
Lillard (35) / Simons (13)
Powell (32) / Simons (8) / Batum (8)
Grant (16) / Little (19) / Batum (13)
Siakam (32) / Grant (16)
Nurkic (28) / Plumlee (20)
I really like the idea of a Dame / Batum / Grant / Siakam / Nurkic lineup. Tons of size, playmaking, and defense in that unit.