Since Dame apparently gave an ultimatum of improve the team, i.e., trade the pick for vet help, he has to realize that is a difficult task to do.
Why?
It's rarely been done. Find me a team that has traded a top 3 pick for a vet player AT the time of the draft (or after). There are examples of picks being traded for vets, but usually that is a future pick, sometimes years away.
It's not as easy as "hey I like this player, he should be my teammate". Dame may like Mikal Bridges, but so do the Nets. And there are some players that Dame has liked and wanted to be teammates that didn't exactly set the world ablaze once they were Blazers. Players don't always make the best GM or talent scouts, and even rarer do they make good decisions based on the entire fitment of the team (ex: Carmelo Anthony made no sense to the team, but Dame advocated it).
The story is after the meeting he said "get me help, I'll give you time" and then not even 24 hours into the FA period he demanded out. Did he honestly expect them to get anything done in not even 24 hours? What players were signed that could've A: been signed by the Blazers and B: made sense to the Blazers?
Despite what some people think, it's not a black and white world out there. Saying you plan on trading to improve the team doesn't mean you HAVE to trade. You look into it, and you make a choice. Trading away a combo like Simons + #3 +23, Simons + Sharpe, or Simons + #3 + Sharpe, or Simons +#3, Sharpe and the #23 pick, is hamstringing the franchise MASSIVELY, and the likelihood of the team getting a veteran player that would make a difference in the teams current season and future seasons, are slim.
Let's say the team did trade for Zion, and it cost them Simons +#3 + Sharpe.
And even if Zion is healthy, who is the starting SG? Who is the backup? Who is the backup SF? This scenario would mean the bench would be absolute crap (we've seen how that movie plays out). So I can see why the Blazers were reluctant to trade potentially 3 players for Zion.
And that's IF Zion is healthy.
So far the other players that were "connected" to Dame wanting to play here haven't been traded. So is it really Joe and Co's fault that the Blazers didn't trade for Bridges of Brown? Both of which are currently on their teams still? And honestly, it would be another bandaid on the issue of the Blazers not having enough talent all around.
Is Damian, Bridges, Matisse, Grant and Nurk a better lineup than what they have now? Yeah, no doubt. But what's the bench going to look like? Little is often injured, Winslow is often injured, IF they had kept Drew or Cam, of those 4, only Drew is the one who plays...but they're all small. Who is the backup PG? Who is the backup SG? Who is the backup C? They'd have to ride the hell out of the starting 5, and there's no evidence that Nurk can last a whole season anymore.
And is Bridges *enough* better than Simons to cover the losses of possibly Simons, Sharpe and Scoot? Same with Brown.
Bostons roster is better than this mythical Portland roster, same with Denver, LA, Memphis, Milwaukee, Phoenix (even without a bench), Philadelphia. Portland would be probably slightly above the play-in with this team.
And throw into the equation that Brown is either due for, or will soon demand a HUGE salary increase, which given the new CBA could potentially hamper the teams future even more, especially given that it's not really likely that the team would be competing for a title with that roster (which is the only way you can realistically justify spending that much in salary and future assets).
Dame has to know that (I know he's confident in himself and what he could do with a starting 5 I list). Otherwise, he's delusional about what realistic things they could do.
Dame knew what he was doing, and it seems more evident that he did this on purpose as to make the team look like the bad guy and not him.