The Truth About The Most Successful Pirate In History

Pirates have been fascinating people for centuries. Often portrayed as villains, tales about how they make fortunes by stealing merchants’ vessels have inspired countless books, movies, and TV shows — which sometimes feed into false facts. Although people often remember stories of pirates such as Sir Francis Drake, Blackbeard, and Captain Kidd, the most successful pirate in history was a woman, according to Atlas Obscura.

Ching Shih was born in China in 1775, and she worked as a prostitute on a floating brothel until she met her husband, the pirate and Red Flag Fleet commander Cheng I, also known as Zheng Yi Sao. As reported by The Culture Trip, there are different tales about how the pair entered a relationship. While some sources claim the pirate captured his favorite concubine, others say he made a formal proposal asking her to marry him. Nevertheless, Ching accepted the marriage proposal, but she had some conditions. One of them established that they would have an equal partnership of the boat, and each of them would keep 50% of anything attained (via All That’s Interesting).

Ching Shih increased the Red Flag Fleet's power

Cheng I and Ching Shih married in 1801 when the commander of the Red Flag Fleet had 200 ships. Ching became a successful leader, and soon they had approximately 1,800 boats. The leading ship had a red flag, while others had black, white, green, blue, or yellow flags, All That’s Interesting reports. When Cheng died six years after their marriage, Ching became the commander of 70,000 pirates. In comparison, the famous pirate Blackbeard only had four ships and approximately 300 men (via Atlas Obscura).

Ching was focused on business and military strategies and created her own tax laws. Before distributing any plunder, it had to be presented to the fleet and registered. She made a collective fund for the fleet, where they kept 80% of the value they received after capturing a ship (via Ancient Origins). She also had strict rules for prisoners, especially females. When a woman was considered ugly, she was released. However, pirates could choose to take pretty prisoners as their wives as long as they were faithful and took care of them. Those who didn’t follow the rules were executed.

Ching Shih was known as “The Terror of South China”

Ching Shih created the rules to control the Red Flag Fleet. She soon became known as “The Terror of South China,” and her power was not limited to the sea — the pirate also controlled villages by the coast, where people were forced to pay taxes to her. If someone didn’t pay, Ching punished them by nailing their feet to her ship’s deck and beating them (via Ancient Origins).

The pirate and the Red Flag Fleet became unstoppable. Powerful navies such as Qing dynasty officials, the Portuguese navy, and the East India Company tried to defeat them for years. And unlike other pirates, Ching didn’t have a tragic death. At some point, she decided it was time to retire and accepted amnesty from the Chinese government in 1810 (via Atlas Obscura).

Although it is easy to assume Ching didn’t have financial problems, there is no information about how she lived during her retirement. She died in 1844 at age 69.

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