Ching Shih - The Pirate Queen of China - From Prostitute to Pirate Lord
Ching Shih was a Chinese prostitute who married a pirate and took over his fleet when he died. She ran her ships with an iron fist and took no shit and was super successful, to the point that the Chinese government sent out an armada to stop her. She kicked their asses and captured 63 of their ships. They fought for two years and even brought in Dutch and British ships before they gave up and offered amnesty to her and her 17,000 crewmen. She got to keep ALL of her loot, spent her later years running a brothel/casino and lived to be 69, (died in 1844).
Ching Shih and her crew's exploits had since been featured in numerous books, novels, video games, and films about piracy, pirates and their way of life in China as well as worldwide. Based on her tremendous influence and achievements as a pirate and commanding the vast fleet of around 1500-1800 ships manned by 80,000 sailors during her peak, she is widely accepted to be the most successful pirate in history.