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Isn't that the point of raising the trading difficulty? To make it harder?
Chase Headley had a good year in 2012 (6 WAR). Other than that, nothing about his stats blow me away (WAR about 3, give or take). Now he's a nice player to be sure, but NOT worth a 5 star prospect. So the AI is behaving exactly as desired.
There are ways to game the system. You need to find the player the AI over-values. And that is rarely veterans. If you can offer him enough of those players, he might be willing to take that veteran off your hands just to make the deal happen.
But finding those over-valued players is the tricky part. If you enable Draft Pick Trading, it becomes a lot easier. But IMO makes the game way too easy.
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