I honestly don't forsee the Diamondbacks being in a position where they NEED to trade Upton.
His contract is fairly reasonable and has five years left on it, he's arguably their best player and still has a ton of upside, I think its fair to say that he's not even come close to scratching the surface on how good he can be.
Kevin Towers will listen to offers, but I'm not at ALL surprised his asking price is as steep as it is.
That being said, I'd be ESTATIC if Boston is able to swing a deal for him and I may be one of a few, but I wouldn't mind seeing the Sox give up Kelly, Bard, Kalish, Bowden and a few other prospects to get him.
Let's be honest here.. Upton's 23.. The majority of the players they would be trading off in this scenario are 21 and older. I'd take established, young Major Leaguer with huge upside and a reasonable contract over prospects any day of the week.