In all seriousness, with all these people who say they know people and that they therefore know exactly what went down in discussions between Dame's people and Cronin, I don't understand how it is that what I think would be the single most likely situation never is brought up.
First, Cronin saying he'd try to use this year's pick to get veteran support for Dame. The problem is, when the Blazers get the third pick and a potentially transcendent player and the return you are getting for that is OG Anunoby IF you throw in Ant and other first-round picks, or maybe you are getting a Tobias Harris-level forward, it makes no sense to trade the pick that became Scoot for that.
I feel pretty confident that had Cronin made that deal, 98% of the people criticizing Cronin for not making a trade would be lambasting him for making that trade that Dame wanted. Dame wouldn't have been held accountable for it, just like he never was held accountable for the other trades to bring him veteran help.
I think ^ this has pretty much been confirmed by the actual people involved.
However, second, I could absolutely see Cronin telling Dame and his representation that he'd try to trade him where he wanted if he wanted out. "Try" being the key word. I'm very skeptical that anyone in Cronin's shoes would have guaranteed that absolutely and backed himself into a corner. I think it's very likely Dame and Goodwin were disappointed that he wasn't immediately dealt to Miami and might have either been taking Cronin's conditional guarantee for something more because of that or never understood it in the first place.
There's going to be a line that Cronin or any GM is not going to cross regardless of what he might have said he wanted to do. If he said he was going to trade Dame to the Bulgarian League and the Bulgarians low-balled us by offering Keljin Blevins and only Keljin Blevins in return, of course he's not making that deal.
Why people think it's realistic that Cronin made an unconditional promise in the first place and are holding him to that regardless of the return is beyond me. It flies in the face of reason.
Finally, Dame did himself no favors here. If Team Goodwin was putting out the vibes that Dame was close to asking for a trade before the draft, he might have, perhaps unwittingly, decreased the market for the third pick, because other GMs thought that Dame was the real prize instead of No. 3, and, they'd either get the third pick and extras for a song or Dame would be in the market and they could make out there. Sharks with blood in the water.
Then Dame didn't keep his word and wait until free agency was well underway to ask for a trade. Then he made it harder for the Blazers to trade with the Heat because he named one team and then he had his agent call all these other teams to tell them not to trade for him so Dame could basically join a Heat team that just played in the finals without having to give up any of its core rotation to get him.
I think that's pretty likely how this all played out, but some people just need to be angry at someone all the time, so knowing what we actually know about how these things usually play out doesn't matter.