Ching Shih

When pirates captured the floating brothel where Ching Shih plied her trade in 1800, she unleashed some serious fury. After marrying the captain (and successfully demanding 50% of all booty), she took complete control when he died in 1807, wrangling thousands of hardened pirates into submission - including castrating rapists. Her Red Flag Fleet of over 1,500 ships and 60,000 men became powerful enough to levy taxes on coastal towns from Canton to Macau, which unleashed the fury of the Emperor. She crushed his forces, then trashed the navies of the Dutch, the Portuguese and the British, making her the most successful pirate in history.