Yeah, Smart to Jrue is a much bigger upgrade than Jrue to Dame.
It is tricky to look at this. In a vacuum, I say maybe Smart ---> Holiday is a bigger upgrade than Holiday ---> Lillard. But if you are going to line up Smart and Holiday, you still have to account for Brogdon and RWill, and also Grayson Allen. I think for the Celtics, it might look like this:
Smart ---> Holiday
Brogdon ---> Pritchard
R. Will ---> Porzingis
Grant ---> ??? (Brissett)
For MIL:
Holiday ---> Lillard
Allen ---> ??? (Beasley?)
I know that Grant has no direct connection to this trade but he is in the equation also is you are looking at overall changes to the roster of the two teams. There are other minor changes on both teams but I see these as the main ones. Jrue Holiday is a nice player to add to replace Smart. He is an upgrade, really the perfect guy to assume that role. And I really like Porzingis, I think he is a great addition, the prototypical scoring big we have been looking for.
But the cost of adding Holiday is losing Brogdon and RWill. It is hard to one to one these comings and goings. But if Holiday replaces Smart (I think that is fair, Holiday will take Smart's spot in the starting line up), and Porzingis replaces RWill (also fair even though 2 different trades), I see Pritchard as replacing Brogdon's minutes and Brissett replacing Grant's minutes.
Net - Net, I see the Celtics as still ahead of the Bucks.