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If CYDY goes from .60 to $20 in a hurry (buyout offer, for example), a short could have been successful 50 times and still lose bigtime.

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A short is only at risk of losing borrowing fees before they sell. When they sell if they're smart enough to cover on the drop caused by the short the only risk from a catalyst is if it's announced after the sell and before that short time to cover. The other risks are that many shorts are covering at the same time and they are last in line or FOMO or buy side manipulation causes a sharp rise in price unexpectedly.

Shorts can get crushed but usually only the dumb ones.