TL;DR: Means “sell/buy something for a tiny fraction of its ‘true’ value.”
Imagine you are a thief. You stole a thing that is worth good money. Say, a diamond ring, 14k gold, big fancy diamond. *Easily* worth $3000.
But you *stole* it: it’s a hot item, and real distinctive. Engraving, fancy patterns, heart-shaped stone, the works. Distinctive is bad. You gotta sell, *yesterday.*
You *could* wait, sell it for thousands…but you don’t have that kind of time. So you sell at $270 to a fence. Fence can work more slowly, and pockets the (huge) difference. You sold for “pennies on the dollar” because you made only 9¢ per $1 it’s “really” worth.
Buyers love this, of course. E.g. say a game company goes under and has to sell its IP to pay off debts. Buyers can nab expensive, popular IP “for pennies on the dollar”, as the ex-company’s need for liquid assets outweighs its desire to get full price for the sale.
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