Actually, one clarification...if he sold something previously to those he is now scamming he probably did so with a different account name. Obviously. So I guess there really isn't a way to know whether you have previously done business with this same person. Maybe he only has access to someone else's account and can tell what you are buying and your actual email address...then he sends the fake scam emails to people he has matched to other sales as low bidders. Sophisticated but not at all out of the realm of possible. It would not require an inside job at all...just access to a legitimate buyer's account and the time to match email addresses to under bidders on other people's items.
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