To answer some of my own questions...
Given 20/20 hindsight, I don't think I'd do the deal. The reality is that Porzingis is a generational talent, which is the first and most important piece to build a legitimate contender. But on the draft night, given how I felt about him being unready to make an immediate impact (or live up to the hype) I think I would've traded down and try to recoup as many assets as possible. It seemed like the safer thing to do and would have better positioned us to make other moves for veterans to surround Melo with.
As for the Magic deal, I would've tried my damnedest to offload Calderon's contract in exchange for a serviceable player or expirer AND the 5th pick. Heningan was sold on Porzingis since the 2014 draft and was rumored to be willing to draft him 12th instead of making the Dario Saric deal that inevitably brought Elfrid Payton to Orlando. Knowing that, I think it stands to reason that Channing Frye, the 5th pick and possibly Andrew Nicholson or Mo Harkless for Calderon and Porzingis would be something he'd jump at.
If that deal were made, I'd take Winslow at 5 and then trade him for the Celtics package and draft the following:
2015
16th: Bobby Portis
19th: Jerian Grant
28th: RJ Hunter
2016
3rd: Kris Dunn
Skal Labessire (if that 4th pick was in the 2016 draft)
None of these guys (as well as Channing Frye and Andrew Nicholson/Mo Harkless) project to sway a game to the extent Porzingis will but would still form the basis for a pretty intriguing team. I wonder how they'd all mesh on the floor with Melo...
