Pengwin, I respect the hell out of your posts, but I think the reason you don't make many trades is this:
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People aren't going to win a trade with you.
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Anyone who is approaching trade discussions looking for a "win" is more likely to fail in succeeding than someone looking for a win-win.
It's all well and good for me to assume I know better than another GM what his needs are, but I'm pretty likely to be wrong since perception is a huge chunk of valuation. If I think a GM's LW is weak and want to put strong LW in a package for a player of his, but he thinks his LW is just fine then I'm barking up the wrong tree from the start. How is the other GM supposed to know what I think my team needs are?
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You are suggesting that the other GM needs you to hold his hand to figure out what a good trade is for YOUR team.
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It's only a negotiation once interest is established from both parties. If I'm not yet interested in moving Player X, why is it on me to figure out what the other GM should offer me to make a trade happen? Why would I be interested in doing that work? If I'm making a trade proposal, I want to have an idea of what the "win criteria" are for my counterpart. If I don't have the pieces on my roster to satisfy those criteria then maybe I can go get them if I'm serious enough.
If someone comes to me sniffing for Malkin, I don't want to deal Malkin. I'm not going to go to their roster and figure out what combination of players it would take because I'm not motivated to do so. I'd respond to them with "well, Malkin is a hell of a player, but I know I've got some holes at G, LW, and D so if you could offer me serious upgrades there maybe I'd consider it."