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”.
Six years later her husband died in Vietnam, creating a void for the leadership. Not yet the heir apparent, she used great political skill to build alliances and friendships. Before long she was undisputed leader, a position she claimed without conflict.
Ching Shih and her army of pirates raided villages and markets along the Chinese Coast, defeating all who stood in her way. Not only did her band of pirates leave everything in their wake, they exhibited a level of brutality that sent shock waves through the enemy. One account reportedly saw captured enemy combatants feet nailed to the deck, then they were beaten senseless. In all, the Chinese navy lost 63 ships, and even the world’s super power of the time, Great Britain, couldn’t stop her. A truce was the only option.
In 1810 the government offered amnesty to all pirates. It seemed like the only way possible to end the lawlessness. However, things didn’t exactly go to plan. The sticking point in the negotiations was the loot, and Ching Shih kneeling before the government. This was an unacceptable demand, as kneeling before the defeated foe was simply out of the question.
After continuing the negotiations, the feuding parties came to a compromise. Ching Shih’s son would be married, which required government consent. During the ceremony Ching Shih would kneel, and it would be accepted as kneeling before the government. So she effectively avoided kneeling to the government, and also got to keep all the loot. Later that year she retired from piracy, being one of the few pirates to accomplish this feat. In doing so, she proved that she was the most successful pirate of all time.