This has Portland giving up the most to get both Brown and Trent Jr. The Heat give up the least (they may have to throw the Raptors a pick swap or two) to get Lillard. The Celtics essentially make a one-for-one trade for Siakam/Brown, which seems fair. Siakam is probably a bit cheaper.

The Raptors rebuild, picking up Herro, Sharpe, a couple young players and three first round picks and some seconds. Honestly, it's not the greatest haul of all time, but if they're staring at the possibility going to lose both Trent Jr. and Siakam in free agency for nothing the way they lost FVV, this is a no-brainer. They can keep Herro and hope that he and Sharpe turn into their backcourt of the future or flip him for more assets in the future. 2 First rounders from the Knicks?

I think this makes the Celtics and Heat even stronger contenders than they already are, and sets Portland up for a chance to contend in 3 years when Scoot turns 21/22 and (hopefully) makes a leap, Brown turns 28/28, Grant is 32/33, Simons is 26/27 and they find a way to upgrade at the center position.