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I like the guy a lot and agree he's proven himself to have a solid floor and unclear ceiling. Still, if I were to trade a potential centerpiece for him I'd either do an even trade (if Nate was a particularly good fit and the potential centerpiece wasn't) or I'd be the one asking for more.
There are so many reasons why you might not be getting what you're looking for. Scouting, league depth in OF, needs of other teams, skepticism about a couple of his tools, etc. Overall, I think you'll have more fun playing out the game without forcing the AI to behave the way you think it should and instead appreciate that a good sim is going leave you guessing sometimes - just like real life baseball.
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