They have done really well... KD to the Suns... Brooklyn did well. AD to the Lakers... Pels did well. Even though it was one team.
Probably not doing as well, but I doubt anyone in the league is viewing the Damian situation as a problem... "You mean that our extension rules created a situation where a team only got 11 super valuable years of service from a star who then asked to be moved to one team and only got 2-3 firsts and a couple good young prospects.... GASP... CHANGE ALL TEH RULEZ!!!"
What Portland gets in the trade is as much of a function of selling a year too late instead of a year early and not reading the market properly, as it is Damian deciding he only has one team on his list. Had they looked around and said... "hey this ain't working lets go to market with Lillard" they might get the mega-deal or have a bunch of different options. The destination he picked has about as much as any contender has to offer in a trade right now. More than the Lakers, Clippers, Suns, Bucks, Nuggets, and Sixers? can offer. Celtics can offer Brown but not sure they do that even if they were on the list. You don't get a prime return on your premium assets unless you time the market perfectly like Presti and Ainge.