2. Blazers trade Anfernee Simons
The Blazers have already been through the Simons-Lillard backcourt, and it's unlikely they want to go through that again. Both are highly talented guards and some of the best shooters in the entire league, but it was apparent when they played together that they had too redundant skill sets. The Blazers don't need another undersized guard who is a defensive liability.
It also appears that their future backcourt will be Scoot Henderson and Shaedon Sharpe. Simons' role and fit with the Blazers are already questionable entering the 2024-25 season; the only way they bring another version of Simons into the equation is by trading him away. An aging Damian Lillard would still be a valuable contributor for the Blazers and could serve as a veteran mentor for Scoot and Sharpe in ways that Simons couldn't.
He would be towards the end of his career, but Lillard relies on his shooting and skill set more than his athleticism, suggesting he has multiple productive years remaining. Simons would also net a lot of trade assets in a potential deal, while the Blazers could acquire Lillard in free agency without giving up anything.