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So this is just hypothetical. But let's say that a big firm shorted $PHUN last October at $5.00 and it went to $20.00. They are down 300% but that's just on paper. They don't cover. They just keep shorting because they know it's going to be a $2.00 stock again.
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For trading firms like $GS etc that have unlimited resources. There is no such thing as having to cover and losing money on a short squeeze. They will just hold that losing position until the stock comes back again and they make money.