As a dealer I've run across scenarios like this, both in my own dealings and being within earshot of other dealers.
A lot of dealers are sharks. They would feign ignorance, buy it for pennies, and crow to others about the deal they got, as someone in this thread mentioned earlier.
Whether I'm buying a $10 lot of commons or a $3000 card I always ask the seller what he's looking for. I also always have a price in mind when I do so. I do this for two reasons:
1) If the seller thinks what he has is much more valuable than it is, I don't want him thinking I am lowballing him, and risk having him turned off from the hobby, telling others I'm a crook, etc. I can't tell you the number of times someone with a 5000 count box of 80s commons has wanted between $200 and $500 for it.
2) If the seller isn't aware of the value, I tell him I'll pay more.
Even though I think the show is scripted crap, you can see the latter happen sometimes on Pawn Stars. To me, it's the right thing to do.
In general the number in my head is the max I'm willing to pay. No one would willingly want to pay the max they're willing to pay for anything.
If someone comes to my table with a $300 card, and I'm willing to pay $175, and he asks for $20, I would tell him that's not nearly enough, let him know what he has is valuable, and offer something more like $125. He's happy and feels treated appropriately. I'm happy because I got a card I wanted for less than I wanted to pay for it.
Now, as for whether the reverse is true...unless it's an egregious error on the dealer's part, or something that I think wasn't intended (ie, a card clearly out of place, or with an unfinished price tag or misplaced decimal) I don't report price discrepancies. If the seller doesn't realize what he had - I don't make it my mission to inform him unless I don't want the card. I've sold $20 cards for $1 because I didn't realize what I had, and I've bought $20 cards for $1 for the same reasons. To me that's because the dealer - the person who is making his money and possibly his living off of this - should know what he needs for his cards.
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