Doing all the "what if" speculating on the trades around Porzingis and Holiday, is futile, but interesting. In particular, if the first Porzingis trade had gone down, it would have included Brogdon going out, but not much else, and no picks coming back. So if that trade had gone down, the trade for Jrue Holiday could have been Smart, Williams and no picks. So really ending up pretty much in the same place either way. It ended up being Smart, Brogdon, and Williams out, Porzingis and Holiday in. The picks ended up netting out, more or less.
I think BOS/Stevens still end up trading for Holiday in either case. Maybe the second trade includes Smart to MEM and picks and players to POR, something like that. Or who knows, maybe MEM and POR strike a deal and cut BOS out.
The speculation part is are we better off with Holiday or would we be better off with Smart and Williams. Smart got traded first, so this is hypothetical, but not entirely unrealistic. Since we have won one championship and are the current favorite for another, it is hard think we could be any better off in any scenario.