This situation seems pretty straight forward to me. Dame said he doesn't know where his future would be and said that this roster isn't good enough for him. Multiple reports and teammates say he's all in right now. Dame says he's here, for now. If the team is still mediocre, which they will be and Olshey hasn't made any moves to make us better than mediocre or at least point us in the direction of getting better, Dame will demand a trade probably earlier in the season than even the deadline. Dame isn't being cryptic and I applaud him for that.
At the same time, Olshey hasn't held his annual pat himself on the back/make excuses presser that comes before training camp. So maybe, just maybe, Olshey has a plan to keep Dame. That would mean making a bigger move than he's ever made but we have the pieces to make a move like that and still have an improved team.
We have very talented starters with only Norm being trade restricted and no one would say any of them are overpaid except for those that say CJ is. We have all of our future firsts. We have an expiring contract like DJJ who is young and talented enough for a team to want to give a try out to, which puts extra value on that expiring deal. We have two prospects on their rookie deals in Ant and Nas that other teams might value even higher than a future first. We have the pieces to make a very big deal.
As far as Ben Simmons is concerned, if Morey isn't willing to wade into the shitstorm that it would be bringing Simmons into the regular season with the Sixers then he ain't getting Dame. I don't think Morey is keeping Simmons that long so Dame is off the table for him... he's got to be coming to that conclusion. At the same time there are also other guys out there that can be had that aren't Ben Simmons and aren't even on our radars because we don't work in NBA front offices.