Just to reiterate: Morey really wants Dame. He realizes Dame may not be available by the time he is forced to trade Simmons. But he believes that Dame WILL be available in the next year or so. Solution? Trade for a package that will be attractive to a rebuilding Blazers' team. Shit, this means he could trade Simmons to someone like OKC and just get a shit-ton of their picks back. But what it CERTAINLY means is that he WILL NOT trade Simmons for CJ, for two very good reasons:
1. If CJ is his asset, then there's no way he can trade for Dame when (he believes) Dame becomes available. The Blazers would not do that.
2. If he gives the Blazers Simmons, then that might buy more time for the Blazers before Dame asks out.
So... I believe that the only way Morey trades Simmons for CJ is if that's literally the only offer he's got. And we KNOW the Wolves are chasing Simmons hard, and we don't know if Olshey has even considered a CJ-Simmons trade.