OK, this isn't a prediction.
Anyway, for the sake of argument, let's say Anfernee Simons gets enough playing time to show what he can do, and sooner or later during the upcoming season, or more likely the following season, overall he becomes a better player than Damian Lillard, if only by a small margin. But even that obviously would be a huge development.
Maybe his effectiveness as a scorer is nearly identical, which would be notable since Lillard shot a career-high 52 % effective field goal percentage last season. Though 52% is above average, it's not mind-boggling, so let's say Simons scores at that level and does a better job of passing to moving teammates (hopefully there are some) or something similar making him clearly (if only by a little) better as the primary ball handler. Maybe he gets the ball up the court much faster, which I think we'd all like to see. In any case, to most eyes he becomes a slightly better (at least) point guard.
My question is this: How much better would Anfernee Simons have to be over Damian Lillard for Anferee Simons to be a starter, or the starter? Would being clearly a little better be enough?
Or is it just not going to happen?
Then, there's this: Lillard will be signing a Super Max contract that will keep him with the Blazers for the next 6 years.
How much does this matter when the coach gives roles and playing time to another guy who can play PG slightly better than the guy getting the huge contract?