Boston Trading for Lillard would instantly help them forget this past post season.
Why would Boston do this? Brown is well known for not using both hands effectively. Meaning him and Tatum make it easy to scheme against. As for Smart it's simply time to move on. They have Brogdon and Derrick White. Bringing in Dame gives them everything they're currently missing. And the new CBA means they'll be in cap hell with or with out Llillard. So they may want to try a different approach moving forward.
Portland does this to get something in return Dame. Dame is amazing. But he's 32 and I'm just not sure anyone is giving up multipe picks giving what he's owed on his contract. But getting two defensive minded young players keeps Portland on the road back to the playoffs and we remove the shadow of Dame hanging over the team and affecting logical thinking at the moment.
Why do the Magie make this trade. Anfernee Simons is going to be better than anyone they get at Pick #6. They are shooting for the playoffs and I'm not so certain about either of the Thompson Twins. As primary playmaker and knock down shooter, he's going to be better off with a younger squad where he can grow as a leader. Suggs has been a relative disappointment since his days at Gonzaga and they have several lead guards. But none who score as Ant does. The Magic frontcourt kept them relevant and I think they realized the need to round out the team with a scoring guard. Moving Carter Jr. is wise because they'll have to pay others in two years and will lose him for nothing anyway.
Why the Spurs make trade? Wemby is 7'4" and Very Skinny. He won't be read y to bang against NBA players yet. Nurkic is cheap protection. He only has 3 yrs on a good deal and at the end of his deal, They can pay Wemby and move on from Nurk or keep on smaller deal. The Picks just load up Spurs with future draft capital, and we move up in the Second round. Graham is a vet shooter and cap filler. He will get to increase his trade value as he takes the shots Dame and Ant would have.
Lastly I'd flip Marcus Smart to the Thunder. (They need a vet and getting Smart only costs them cap space for 2 years) Blazers pay Thunder in 2nd round picks and gain 18 million imediately.This would ultimately leave Portland with very healthy cap to sign Grant and Porzingi and we're no longer in salary cap hell moving forward and could have both of those guys under 30 years old and on non super max deals. I think we're as good or better than last year with more size and defense at every position and every bit a potent offensively.
That being said, here's how I'd finish the off season.
Pick #3 Scoot Henderson
Pick #6 Taylor Hendricks
Pick #33 Amari Bailey
Pick #43 Tristan Yukcevic / Emoni Bates
Free Agency after all the above moves and we're left with ~45 million after all the dealing, having gained +27 million from trades.
PG Henderson (Draft Pick)
SF Jaylen Brown (Trade)
PF Jerami Grant (Free Agent)
C Porzingis (Free Agent)
PF/C Carter Jr (Trade)
SG/SF Thybulle (Free Agent)
SF/PF Taylor Hendrics (Draft Pick)
PG Suggs (Trade)
PG/SG Graham (via Trade)
C Badji (Two Way)
PG/SG Bailey (Draft pick)
C Tristan Yukcevic (Draft Pick)
Last part of the trade to move Marcus Smart.