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Yep - Upton is a big-time talent, but he can be Ruben Sierra just as easily as Juan Gone.
I would trade breakable items for him.  I love Pineda, but pitchers break.  When we threw a bunch of pitchers at Erik Bedard, that wasn't my concern with the deal.  Years later those minor-league pitchers aren't doing anything special, and we found a suitable replacement for Jones.
The rumored package for Upton would be one that would fill many holes on the D-Backs roster: something for the OF, a significant starting pitcher, a closer-type, and change.
I would do Saunders/Pineda/Cortes to fill those 3 needs and throw in another minor leaguer (Poythress?) or two.  If they don't want Saunders I can throw in Gutierrez and move Saunders to CF, which he CAN play - though not as well as Franklin does.
But at that point Saunders doesn't have to hit like Upton to have value.  His bat should play better in CF than Franklin's, plus we save Franklin's salary the next coupla years to make roster moves easier.  I like Guti and our park doesn't kill him like it does other righties, but he's abysmal against RHP - which he faces 2/3 of the time.  He's not gonna get that much better at it IMO.  Last year's better numbers came almost entirely because he killed lefties last year and did poorly against them this year.   I would move him for a better righty for the lineup.
Upton is far from perfect, but he's got oodles of potential.  He hits Righties 150 OPS points better than Guti and kills lefties better too.  His road splits scare me, and his K/BB isn't great, but I don't need him to be a 160 OPS+ monster for him to have tremendous value to this offense.
We can get Upton if we want him.  Pineda is the best pitcher available, I would think. We can offer one of a couple of outfielders, a couple of rocket-armed pen guys if necessary and some 30 HR potential minor leaguer.  
We can get him without Ackley or Smoak, which is important, because neither guy will or should be involved.  Ackley is production from day one with his skillset, and will be for a dozen years.  I don't give that up when I'm trying to remake a team with the highest-percentage shot of sustained success.  
I don't think we'll try for him, and I would still prefer Rasmus for the same package, but we could get him fine without using the Batman and Robin of our next half-decade to do it. 
~G

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