This one is more out there in Damian Lillard trade ideas. The Blazers would receive most of their very high asking price, only 1 pick short. This would likely assume that they believe in Anunoby to expand beyond his 3&D role, something he has expressed interest in himself. This would also mean that Toronto would have to once again unexpectedly join the Dame sweepstakes, similar to how they traded for Kawhi when he was dead set on LA.
Trail Blazers:
Receive a package headlined by OG Anunoby
Christian Koloko as a young piece
Veterans for frontcourt depth
3 unprotected 1st round Picks
Raptors:
Receive Damian Lillard
Hope to make a deep run with a star that did not request to go to Toronto, much like they did in 2019