This is a spectacular example of why you should never judge a book by its cover. The most successful pirate of ever was a young, attractive female prostitute from China named Ching Shih. At the height of her power she commanded up to 1,800 ships , and up to 80,000 men, women and children. She practicality had an army at her disposal. While certainly not as well known as others, such as Black Beard and William Kidd, she was just as flamboyant, terrifying and ruthless. But apart from being female, she managed to do something that very few of the other male pirates seemed to be able to do, and that was retire instead of being killed.
Ching Shih started her working life as a prostitute in the city of Canton. While working as a prostitute she was captured by pirates and in 1801 she married Zheng Yi, a notorious pirate in his own right. This was her first step to becoming the most successful pirate ever. However, despite her massive success, a success that’s practically unrivalled in her field, she is still best known as “widow of Zheng”.