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The Most Successful Pirate Known Was Actually a Woman

Ching Shih ruled the waves with a fleet of a thousand ships

By Sam H ArnoldPublished 5 months ago 4 min read

Ching Shih (or Zheng Shi) was a Chinese prostitute who became a powerful female pirate, controlling the infamous Red Flag Fleet.

She ran the fleet like an organised system of business. She ran a Mafia-style organisation with both illegal and legal endeavours.

Early Life

Little is known about Ching Shih's early life. However, it is known that she was born in the Guangdong province of China in 1775, and her birth name was Shii Xiang Gu.

The region she lived in was poverty-stricken, so she became a prostitute who worked in a floating brothel in Canton.

That was when she met Pirate Zhèng Yi. There are varying accounts of how they came to be together. One version states that Zheng Yi raided the brothel with his pirates, taking Ching Shih prisoner. Others state that he met her, fell in love and wooed her romantically.

Ching Shih, the Pirate

Whichever the actual version, she agreed to his proposal on one condition. She would have equal power within his organisation. The couple went on to run the Red Flag Fleet together.

With her guidance, they quickly grew the fleet from 200 ships to more than 600, eventually reaching between 1700 and 1800 ships.

The ships were organised into different divisions like an army. They were named Black, White, Blue, Green and Yellow. The final fleet which the couple took personal command of was the most feared, the Red fleet.

Tragically this union did not last long as Zhèng Yi died in 1807, after only six years of marriage, at the age of forty-two.

Widowed and Married for Power

Before his death, Zheng Yi had adopted a twenty-year-old farm boy. Some state that the three of them were actually in a relationship. When Zheng Yi died, his son Chang Pao inherited the fleet. However, Ching Shih craved the power and glory of being the leader.

She placed Chang Pao's as head of the red fleet and with his help, continued leading the pirates. The couple started a relationship shortly after this and eventually married.

One of her most famous battles was against the Qing Dynasty, who set their Mandarin navy vessels to confront the Red Flag Fleet in the China sea.

After a few hours, the navy was decimated and suffered considerable losses to Ching Shih. The crew that survived chose to join the pirates or be punished.

This resulted in the Qing Dynasty losing a vast proportion of their army and growing the pirate troops even more.

Laws and Taxes

One of the factors that made Ching Shih such a successful leader was that she bound her group of pirates to a series of laws and taxes. Any loot they blundered, they could keep 20%; the rest went to the entire fleet.

Rules governed the treatment of captured prisoners, especially women. If the woman was considered ugly, she was released unharmed. A pirate who wished to take a beautiful female captive as their wife was free to do so, but they were bound to be faithful and to care for her.

Break these rules through unfaithfulness and rape; the pirate was executed. Deserters would be hunted down and their ears cut off.

Through this code, Ching Shih remained in control of her fleet. The fleet even moved inland, taking control of many coastal villages. Again she imposed the villages with levies, taxes and strict rules of conduct.

An Honest Living

This reign continued with the fleet defeating Chinese, Portuguese, and British naval ships.

In 1810, when it became clear that the Portuguese outgunned the fleet. Moreover, the alliances of the coloured fleets had broken apart, reducing their power.

Ching Shih started negotiations with Qing Emperor Jiaqing. Then, using the secrets she learned as a prostitute to wield power over the wealthy and political, she negotiated a deal of surrender with the government.

She and Chang Pao ended their lives as pirates with a full pardon from the government and were allowed to keep the loot they had amassed.

Chang Pao was given a new name and became the leader of a government-formed pirate hunting fleet that went after the last of his fleet.

Once again, in 1822, Ching Shih was struck by tragedy when Chang Pao died at sea. She had mothered both a son and daughter by him.

Ching Shih returned to Canton and opened her own gambling house. She also invested heavily in the salt trade in the area.

In later life, she went to Macau and started a brothel, where she remained until 1844 when she died aged sixty-nine.

Her Legacy

Today her descendants are still said to run gambling and brothel enterprises in the same area.

Ching Shih was a truly remarkable woman and leader. Her strength and courage made her a powerful adversary in the China Sea.

To put her achievements in context, Blackbeard, one of the most infamous pirates, only commanded four ships with three hundred pirates. Yet, it is believed at the height of her control; she had tens of thousands working for her.

She is the most successful pirate in history and was the inspiration for one of the characters in the Johnny Depp franchise, Pirates of the Caribbean.


About the Creator

Sam H Arnold

I know where the bodies are buried and I’m not afraid to tell you - author of True Crime, History and Fiction. Find me on Twitter [email protected]

Or find my crime magazine here -

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