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Taking thing into an OOTP context: Does the AI plan to sell off its best players when it has a certain winning percentage or when it is X games from 1st?
I'd rather do whatever setup means I have as few player dumps as possible (and yes, I do set trading to low), because the AI in my experience will do things like trade Barry Bonds for 5 minor league guys just because the Giants were having one bad year, something I don't think is realistic.
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