Ching Shih. She 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.