You make the deal 101 times out of 100
Not necessarily.
Noel win shares last year: 3.0
Smart win shares last year: 2.9
Noel win shares/per 48: .074
Smart win shares/per 48: .083
Noel VORP: 1.3
Smart VORP: 1.1
By most metrics Smart is about as valuable as Noel. Now there's an axiom in the NBA that you want the good big man over the good little man. There's a premium on size. So even up you make that trade every time if other things are close to equal (like leadership, clubhouse personality, etc.). But when you throw in the 16 and the 23? Now the price is pretty lopsided.
I'm not saying it doesn't happen but it's certainly not a sure thing. That's a high price to pay for the premium of size. It all depends on someone's projections of player development, team needs and so forth. Personally, I'd do Smart +23 but not 16 because I see that mid 1st pick as too valuable. Those mid-1st have been Rozier, Olynyk, Sullinger, Bradley and Jefferson during Ainge's tenure. That's a pretty decent track record and I generally wouldn't include any of those guys along with Smart and 23 for Noel.