The Most Successful Pirate in History was a Chinese Prostitute named Ching Shih

The Most Successful Pirate in History was a Chinese Prostitute named Ching Shih
The Most Successful Pirate in History was a Chinese Prostitute named Ching Shih


As soon as you hear the word “pirates,” your mind immediately evokes images of skilled, fearsome individuals who have captivated generations of youngsters and adults alike for more than seven centuries already.

Readers of history may recognize the names of Blackbeard, Barbarossa, Henry Morgan, or Sir Francis Drake. It is widely accepted that these men were fearsome pirate lords that terrorized ‘the Seven Seas’. What is less known is that the most successful pirate in History was a Chinese prostitute named Ching Shih. A remarkable Asian woman whose name translates simply as “Ching’s widow”.

Her journey from rags to riches is nothing short of thrilling. More than 80,000 men and women served under her as crew members on 1800 ships at the height of her strength.

From Rag to Riches

Ching Shih was born in Guangdong province, China, in 1775 as Zheng Yi Sao (a.k.a Shi Yang, a.k.a. Shi Xianggu), the daughter of a poor farmer. At thirteen, like many other girls her age, she was pushed into prostitution to help support her family’s living expenses.

She was a prostitute on a flower boat. Flower boats were floating brothels in the coastal city of Guangzhou (formerly known as Canton). Customers would be transported on board these vessels while they cruised the adjacent coastline.

Chinese people at the time believed that the movement of the boat provided a new depth to sexual delights and enriched the whole experience. Because of her outstanding beauty, calm demeanour, and kind hospitality, young Ching Shih quickly rose to fame.

High-ranking royal courtiers, army generals, and wealthy businessmen visiting the port city were among the numerous clients drawn to this establishment. Given her poor upbringing, little is known about her early life.

Chinese Pirate Woman Ching Shih
Chinese Pirate Woman Zheng Yi Sao

An 1801 meeting with a well-known commander of the Red Flag Fleet known as Zheng Yi would pull the prostitute-turned-pirate-lord Ching Shih out of that floating obscurity, and change her life forever. It is said that Zheng Yi, pirate Commander of the Red Flag Fleet, fell in love with and proposed marriage to Ching Shih, who was known for her shrewd business savvy and trade-in-secrets through pillow talk.

This part of events is highly disputed, with some historians claiming that the 26-year-old Zheng Yi had instructed his troops to kidnap Ching Shih from the brothel and forcefully marry her.

Regardless, Zheng proposed marriage to Ching, and it is said that she agreed via a formal contract that granted her 50% “ownership and partial management of [his] pirate fleet”.

Ching Shih reaped the most benefits from their partnership, and her meeting with Zheng Yi is widely regarded as a stepping stone to greater renown, which in turn earned her a place in history as one of the most successful pirates ever recorded.

Ching Shih bore him two sons: Zheng Ying Shi and Zheng Xiong Shi. They also adopted Cheung Po, the son of a fisherman that Zheng Yi had kidnapped in 1798.

The Red Flag Fleet

The Red Flag Fleet grew and prospered like never before under the combined leadership of Zheng Yi and Ching Shih. In the years following their wedding, the fleet increased from 200 ships to 1800 ships.

A tight code of conduct was put in place for the crew, devised by another pirate lord known as Zhang Bao, was put in place as soon as she married her husband, and she enforced it religiously from that point on. Following are just a few notable examples:

  • Those pirates who gave unlawful commands or refused to follow orders were killed on the spot without the opportunity to explain their actions.
  • All seized goods were to be brought to the inspector for examination. If particularly heinous pirates were detected concealing or underreporting their activities, a piece of their flesh would be hacked off.
  • Admirable pirates were paid liberally for their loyalty and honesty, which set an example for the rest of the crew.
The Chinese Junk Keying. (Illustration Public Domain)
The Chinese Junk Keying. (Illustration Public Domain)

The treatment of female captives was critical. They were divided up based on their appearance and attractiveness. As quickly as possible, the weak, pregnant, and unsightly were released.

Ransom money was used to keep the attractive ladies as hostages. Under mutual accord, the pirates were allowed to marry them. An offence of infidelity or rape was viewed as very grave. These criminals were hung as soon as possible. Both perpetrators were executed in the context of pre-marital sex which was voluntary. Some men were castrated and the women were expelled from their ships.

In addition to this, several economic improvements were approved as a show of thanks to the crew. This led to many of the pirate gangs in the region joining together under the name of the Red Flag Fleet, making it the biggest pirate fleet in the world.

Cheung Po (the adopted son) became second in command to Zheng Yi and the second most regarded crew member behind Zheng Yi and Ching Shih. Many crew members were astonished by the decision of the pirate couple to adopt a fully grown man.

Zheng Yi Sao had up to 1,800 ships and 80,000 people under his command in the pirate fleet known as the Red Flag fleet – and China’s naval forces and those of European nations were powerless to stop his 12-year reign of terror over the South China Sea. With Ching Shih at its head, the notorious Red Flag fleet quickly expanded to take over all major Chinese pirate organizations, reaching a peak with a force of 1,800 ships and 80,000 pirates.

In comparison, the famous Blackbeard commanded four ships and 300 pirates.

Tragedy Struck

Zheng Yi died after a severe storm off the coast of Vietnam in 1807, just six years into their marriage. It is said that he fell overboard and drowned. However, many speculations at the time believed he had been poisoned either by his wife or his heir-to-be.

Nevertheless, using her business acumen and connections with the infamous pirate captain Zheng Yi, Ching Shih managed to moderate the power-hungry war captains from the other ships, as well as install her adopted son as second-in-command of the fearsome Red Flag fleet. Ching Shih installed another fearsome pirate lord, Zhang Bao, as head of the confederation of the Red Flag Fleet. They soon became intimate.

Zheng Yi - romanised as Cheng Yud or Cheng I
Zheng Yi – romanised as Cheng Yud or Cheng I

A New Beginning

By 1806, virtually every Chinese vessel along the coast paid the pirates for ostensible protection. For a decade, The Red Flag Fleet had ruled the Chinese seas and authorities were powerless to stop them. More than 12 000 people, including civilians, were killed.

Chinese authorities finally turned for help to the ‘foreign barbarians’ that controlled the region of Macau at the time. The combined fleet of the Chinese and the Portuguese Empire went to war against the Red Flag Fleet and fought extremely bloody battles at sea, where countless lives were lost.

It was clear by 1810 that no clear victory was in sight. Just stalemate after stalemate. By this time, British warships had already joined the Chinese and Portuguese fleets. Infighting ensued among the confederates of the Red Flag Fleet, those from the Black Fleet and the White Fleet, who no longer wanted to follow the instructions of Ching Shih or her aides.

The pirates also began to realize that they were in a position of power to negotiate a surrender to the Chinese authorities without punishment or reparations since they were desperate to end the scourge of piracy.  

Many of the pirates that surrendered were treated with dignity and become admirals or assistants in the Chinese Navy. Many others simply retired.

Ching Shih herself officially surrendered on April 20, 1810, alongside 17,318 other pirates, 226 ships, 1,315 cannons, and 2,798 assorted weapons. At the time of her surrender, she personally commanded 24 ships and over 1,400 pirates.

Zheng Yi Sao died at the age of 68, in 1844. After her surrender, she lived a peaceful and prosperous life. She is often described as history’s most successful pirate.

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