Sanchez is the deal-breaker in that scenario.

I figured might as well start out with an ultra-greedy demand from the D'backs and see if anyone bites. Give people the opportunity to look brilliant if Upton turns out to be a beast. No guts, no glory...

(I am firmly in the camp without guts.)

I think that the chance that Upton turns into a beast is about 10%, about the same odds that he is out of the league in 5 years.  In my view, the most likely scenario is that he remains what he is, as a hitter, and with modestly declining defensive utility over time. 

I wouldn't trade Gose and Sanchez for him, let alone the others. 

I agree that Sanchez is the deal-breaker. I think I would trade any two of Escobar, Hechavarria, Snider and Gose plus either of Syndergaard or Nicolino.

It's funny.  Everyone has a different view of prospects.  I would trade Sanchez for him straight up.  He's a 10% ticket, the same as Upton is (in my view), and the Jays do have a bunch of those long-range pitching tickets. 

I'd put Sanchez as somewhat more than a 10% lottery ticket, but I'd agree with the idea of trading him straight-up for Upton. Because then you've still got the other lottery tickets -- Gose, Nicolino, Snider -- who might be less than 10% each but have a much greater combined value.

Expanding the deal makes it a lot scarier.  Upton for Gose & Snider is easy.  Nicolino & Sanchez are lottery tickets (FYI: avoid just last names when it is a very generic last name - there are tons of Sanchez' in baseball) at this stage thus extremely hard to put a value on.  I can't imagine AA would be comfortable trading pitchers who are now in A ball as their value could be anything.

I'd do it though under the old rule of 'best player in the deal wins'.  Depending, of course, on if the Jays scouts feel Upton will be a 120+ OPS+ hitter going forward with a good shot at 140+.  If estimates are in the 100-110 range then screw it.

I would acquire Headly from S.D. and add Hech plus a young stud and a piece or two for Upton and a Starter (Kennedy). Upton would then highlight a package for King Felix. We would then have a top Pitching staff and an Ace to replace Doc. We would also have time for the 2010, 2011 and 2012 picks to mature enough to start A.A.'s plan.

In my view, the most likely scenario is that he remains what he is, as a hitter

This statement needs context - what is he, as a hitter, in your opinion? Through age 24 he's posted a 117 OPS+ in 660 games. With a normal aging curve going forward that may be short of a "beast", but is a very fine hitter. Especially given that his OBP has been north of .350 every season save for the 43 games he played as a teenager.

On the other hand, if he's the hitter with the 100 OPS+ in 79 games as a 24-year-old, he's not likely to be worth his contract. And on another hand, if he's the hitter with the 139 OPS+ in 159 games as a 23-year-old he's elite in terms of beast potential.

Sorry, Jonny.  I had posted my thoughts in another thread.  In my view, he's currently a 116 wRC+ hitter, and that is where he is likely to remain, with typical seasonal variation.  To put it in a neutral context, he probably hits .270 with 55 walks, 30 doubles and 20-25 homers in an average year.  When you are paying $14.5 million per year (as you will be in 2014 and 2015), that isn't much of a beast.