After your article string on Reynolds, I was worried you'd lost your touch...but I'm back on board now, Doc. :)

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

The M's have got to have a RH hitter somewhere in the middle of the lineup. Upton is young with a reasonable contract and signed for five years. He's not a dead pull hitter, so Safeco wouldn't Beltre him.
I think Towers will not get what he is asking for but it's going to take a lot. Pineda + Gutz + Lueke plus some pieces and parts. Hot, Grade A pitching phenom + established gold glove OF'r whose bat profiles better in AZ + hot, cheap young closer in waiting. Throw in Aardsma and Towers probably has four guys on his 25 man roster for 2011.
I wouldn't trade Ackley or Smoak in a package for him. Keep those two and add Upton and you've got your #2/3/4 hitters for the next five years locked in. We haven't seen that kind of firepower in the lineup in quite a while.

I bet you made an awesome punk teenager on the basketball courts with that kind of trash talk. :D
Seriously though...what the heck were you smoking req'ing Reynolds? :)

Completely agree Doc.
I would do a package centered around Pineda, but not around Ackley. I would also do a package centered around Smoak.
They don't get two blue chippers, but they get one (no Ackley) and significant secondary pieces.
Nobody is going to trade 3 blue-chippers for him, they probably won't trade 2.

Only place I disagree is on Justin Upton raw talent. There are only a handful of guys you can compare him too.
Of course the concerns are the shoulder and the Ks.

Right.
It's not Pineda's chances of becoming great, it's his chances of staying healthy.  Sure, Upton injured his shoulder last year, and there are some Chris Snelling/Jack Wilson cases of hitters who were just too breakable to take advantage of their talent, but for the most part if a guy is a great hitting talent he'll be one for a long time.
A pitcher can be the greatest talent in the world and still crash and burn because of injury.
So it's not a matter of "Pineda has a 30% change to be great, and Upton has a 30% chance to be great, and pitchers are harder to find so we keep Pineda."  As you said, breakability is a factor.  For me, it's a huge factor.
And pitchers with great talent may never manifest it in results.  Pitching is tricky.
Look, we traded four pitchers and a bat for Bedard, a monster starter.  So of those 5 pitchers:
Bedard: two half-seasons, multiple surgeries.
Tillman: Been healthy and a great pitching prospect in the minors - and terrible in two 50+ inning big-league stints in 2 years.  Pineda-aged and Pineda-like.
Butler: Injured, surgery, has not made it out of A-Ball since, terrible and on a new team.
Sherrill:  Terrific slipped to good slipped to injured and struggling in the last 3 years.
Mickolio: Has been healthy but unable to harness his stuff, walks and hits too high, unable to crack the big-league roster and stay 3 years in a row.
How about for Snell and Wilson?  We gave up three guys, all with pro stuff.
Lorin: Injured, surgery, making his way back.
Adcock:  Staying healthy, pitching in High-A for the second time and doing well there.
Pribanic:  Strikeouts declining further, hits increasing, and he hasn't hit AA yet.
Pitching is no sure thing.  On the one hand, that means I want lots of it in case some of it blows up.  On the other hand, it is RARE that I will bet the farm on a dominant starter.  Watching what happened with Oakland's big three after they left was very instructive to me.
Felix was the one I wanted to extend, and I expect him to stay mostly healthy.  Of course, the D-Backs thought that about Brandon Webb, he of the 3 top-2 finishes in the Cy Young.  And then his arm and shoulder blew up.
Pineda's already had one elbow scare.
If I can trade Pineda's 130 ERA+ for Upton's 130 OPS+ I certainly consider doing that, because the odds of Upton being able to do it 5 consecutive years for the entire season is higher than Pineda's. 
If we can get 90% of Upton and keep Pineda, I can see doing that, as you say.  Maybe Saunders IS 90% of Upton.  Maybe he's nothing.
That's why the bets are so hard to place, and why Jack has continually impressed me with his stones and his gut feeling at the trading table.
Pineda is worth a LOT to us, either in trade or in the 2011 rotation.  Having him play for us would be welcome.  If we cash him in instead, I want it to be for an Upton/Rasmus level player.
~G

http://www.mlbtraderumors.com/2010/11/justin-upton-rumors-thursday.html
So it seems, anyway.
G and Doc are right on.
Z has been consistent: lefties fit at Safeco; he likes guys with excellent eye ratios; he tries to put the RH bats at "glove" positions; he likes "character" guys at the core of the team -- he hand-picked Ackley and Smoak to be Exhibits A and B.  Upton -- not so much on any of those counts.  I don't see Dust-n-Smoak in a trade scenario at all.
Pineda is a different kettle of fish.  He's been injured once, hasn't actually proven anything at the MLB level, and can be more-or-less replaced by Gerrit Cole or Matt Purke (who are both a year younger and probably almost comparable to Pineda right now).
We have a few of RH hitters at non-glove positions -- Chavez, Liddi and Poythress -- that don't fit Z's template, and some LH hitters that could be moved (Saunders, Mangini, Tenbrink).
And certainly a surplus of potential bullpen power arms -- Aardmsa on down.
I don't think Z sees any value in Tui or Halman, but he likes to find other GMs who see value where he doesn't (e.g., Aumont).  He's also been "talking up" Peguero, which, to me, could only relate to trying to puff up his trade value.
So I could see a four-player package that doesn't hurt much, in the same way that the Lee-coming-in trade didn't hurt much.

Jack Wilson and 95% of his salary would be in that deal too, if the D'Backs give up their starting shortstop, they'll need someone to replace him, at least for a season.

That AZ has tons that we would be interested in trade, we've already talked about Reynolds, Upton, and Drew a bit, but there's also Kelly Johnson (who was talked about when the Braves had him) and there's been rumors that we're one of the teams looking to make a play on Webb

Rosenthal and Olney need to get their stories straight:
Olney 2 days ago: "Heard this: The Seattle Mariners likely will not be doing a whole lot of stuff this winter, beyond shopping from the bargain bin."
Rosenthal today:  "Mariners not ruling out run for J. Upton. Could build package around RHP Pineda."
If Upton is the bargain bin, I sure want to rummage around in there for a while.
Conflicting reports are fun. :)  Adding legit top-flight talent would be more fun.
~G

By the time Upton gets crazy-expensive we shouldn't be forking over Ichiro's salary any more (maybe).  We can afford him.  Smoak will just be starting to get expensive and Ackley will be a little ways away.  If we've found some power-hitters in the minors by then we can trade Upton.
As for what our package would be for him, there are no links that I've heard of that give that information, just that Pineda would be involved in the offer we make (and yeah, he'd have to be).  If we start with Pineda we're in the mix.  The D-Backs want Bard + Ellsbury + whatever from Boston.  Bard is a great closer-in-waiting, but
We just added Justin Miller as yet another RH relief option, so we might be able to spare a pen arm or two in pursuit of a real offense.
I say Cortes goes, and maybe Lueke too.  One of them can stay if the D-Backs prefer a more veteran bullpenner like League or Aardsma be in the mix.
Pineda is the star of the deal as the #1 prospect in the system (certainly the #1 pitching prospect) and a top-10 pitching prospect nationally, and then we need a ML-ready outfielder and a minor league hitting prospect to throw in.  Saunders or Gutz are our only outfield options for trade, and Gutierrez is by far the more proven (and more expensive) though the D-Backs are looking for a corner OF more than a CF.  Add in Chavez or Poythress or even Halman as potential 30-homer guys and we could have ourselves an Upton. 
It's a tantalizing thought.
So's having Pineda backing up Felix, so it's hard to lose out here.  We just need a good plan B for the offense if we can't win the Upton bidding, that's all.  "I tried" isn't gonna cut it this year, budget restraints or no budget restraints.
~G

"...we have a couple of pro bullpenners and a raft of hard-throwing AAAers to offer of our own, and Ellsbury isn't better than Guti."
That's how it should have read. ;)
~G

I know he had a bad year last year so people are dead convinced he'll never hit again for us ( :-) )...but c'mon now...Gutz is a 4+ WAR player...trade them Chavez or Halman and Saunders...not Gutz.

Guti is a premium pieces and way too underaprreciated. No reason to trade him to a club that doesn't know what they're doing.. This is the same club that traded Dan Haren for Joe Saunders.
Saunders+Johermyn Chavez is MUCH preferrable to Guti IMO, and I think that may be preferrable from Arizona's perspective too.
A deal centered around Pineda is something I'm 100% behind if the Ms are targetting Upton. Go NUTS on secondary pieces. Who really cares? You're not going to get another shot at landing a talent like this.
 

...a trade of Upton for Pineda/Saunders/Chavez/Lueke/another prospect from a PTBNL list of decent B prospects.  Pineda hurts for me to part with...but I do it under those circumstances only.  If they ask for any other player that I'm counting on for the big league roster next year...no sale.

Basically the3 structure I'd be willing to give would be 1+ (one big big spect...several useful pieces).  If they get even one 2+ offer (two big big prospects)...they take that offer...even if the + is just one player.