Who Was the Greatest Pirate in History?

The most powerful pirate in the world was arguably Zheng Yi Sao, also known as “Ching Shih.”

The greatest pirate ever in history was arguably Zheng Yi Sao (1775-1844), also known as “Ching Shih,” surpassing even men, as the most powerful pirate in the world. The power and influence of Zheng Yi Sao were unmatched. For comparison, Blackbeard, who is considered to be the most renowned pirate in the Caribbean, only had a maximum of 4-5 ships and 400 crew members at his peak. In contrast, Zheng Yi Sao had a fleet of 300 ships and a crew of 40,000 men, and she was able to establish herself as a ruler over the southern coast of China and all the cities and villages under the rule of the Qing dynasty.

A Prostitute in Early Life

A Zheng Yi Sao artwork from 1836, colored.
A depiction from The History of Pirates of all Nations published in 1836. (Culture Club / Getty Images)

Born into poverty as “Shi Yang,”  she was sold into prostitution by her parents to pay off their debts. Her beauty and education led her to become a high-class prostitute. However, her life took a turning point when, in 1800, at the age of 25, she fell in love with Zheng Yi (also known as “Cheng I“), the leader pirate of the Red Flag Fleet, one of the most successful pirate groups in southern China that also had access to the finest brothels.

Cheng I was determined to marry Shi Yang and sought to do so through a brothel, but to his surprise, she refused. When he asked for her reasoning, Shi Yang was firm in her refusal and presented him with a condition for marriage: He had to give up his command of the Red Flag Fleet, his future income, and half of his property. Despite this, Cheng I was smitten with her and agreed to her terms. In 1801, they married, and Shi Yang began calling herself “Zheng Yi’s wife” or Zheng Yi Sao.

Zheng Yi Sao’s Influence on the Pirate Fleet

An artwork portrait of the great pirate Zheng Yi Sao.
A portrait of the pirate Zheng Yi Sao. (Artwork: ArtStation – Sandrahl89)

Zheng Yi Sao’s influence on the Red Flag Fleet was significant. Prior to her joining the group, they were just an ordinary pirate crew. However, with her guidance and leadership, they transformed into a well-coordinated fighting force, similar to a navy. Zheng Yi Sao also implemented strict rules for the pirates, including prohibitions on assaulting women and selling them to brothels. Additionally, they regulated the distribution of stolen goods and rewards.

The reason why the pirates were able to maintain such strict rules and still thrive was due to their increased income. The Red Flag pirates focused on a single port and attacked every ship that left it, making it impossible for ships to depart. Since the government navy of South China was weak and corrupt, they were able to get away with this for a while by bribing officials. They also kept other pirate groups at bay and eliminated those who did not comply.

By negotiating with the mayor and major merchants of the blocked port, they agreed to pay a large sum of money to the Red Flag Fleet on a regular basis as a “tax,” in exchange for the fleet’s promise not to attack ships in the city and to exclude other pirates from the area. With a portion of the money, the pirates who obeyed the agreement were taken into Red Flag, and those who did not obey the agreement were crushed. This strategy allowed Zheng Yi Sao and her husband Cheng I to gradually increase their power, and by 1806, they had annexed many pirate groups in southern China and had amassed a huge fortune without attacking ships.

When a Country Couldn’t Defeat Zheng Yi Sao

Piracy in the South China Sea.
Piracy in the South China Sea.

When Zheng Yi, the head of the Red Flag Fleet, unexpectedly passed away, his leadership was thrown into question. However, his wife, Zheng Yi Sao, stepped in, wielding her formidable political power to subdue her rivals and secure her position as the official leader of the Red Flag in 1807. Under her guidance, the Red Flag pirates continued to thrive and dominate much of China’s southern coast through taxation.

In 1805, her fleet of 400 junks had a crew of around 50,000 pirates. It is known that Zheng Yi Sao and her fleet fought against great empires including the East India Company, the Qing Dynasty of China, and the Portuguese Empire.

The Qing dynasty, caught off guard by this turn of events, launched a full-scale effort to crush the Red Flag Fleet in 1808. But the Red Flag, led by Zheng Yi Sao, emerged victorious, capturing most of the Qing navy’s warships. Desperate for assistance, the Qing dynasty of China sought help from the Portuguese navy and agreed to pay a large sum of money to defeat Zheng Yi Sao, the most powerful pirate ever in history.

It’s Time to Retire

In this artwork from the 19th century, we see Portuguese Macao, a province of the Portuguese Empire until 1999.
In this artwork from the 19th century, we see Portuguese Macao, a province of the Portuguese Empire until 1999.

As the Red Flag’s power continued to grow, Zheng Yi Sao realized the danger her pirate fleets were in and approached the Qing dynasty for negotiations. She proposed to retire from piracy along with her followers and move to the Portuguese territory of Macao, taking their wealth with them. In exchange, the Red Flag’s warships would be peacefully handed over, and most pirates would be pardoned. But if the Qing dynasty did not agree to these terms, Zheng Yi Sao threatened to ignite an all-out war in southern China.

The Qing dynasty accepted the terms, and in April 1810, a group of around 17,300 pirates led by Zheng Yi Sao and her adopted son Zhang Bao, along with 225 ships, 1,315 cannons, and 2,800 weapons, formally surrendered to Bai Ling in the vicinity of Furongsha. Zheng Yi Sao also personally surrendered over 24 warships, and approximately 1,400 pirates under her command were also pardoned by the state.

Zheng Yi Sao retired to Macau with her vast wealth, where she opened an elegant and luxurious gambling house. Zheng Yi Sao never returned to piracy again, and she was even hired as a naval advisor by the Qing dynasty during the First Opium War (1839–1842). At the age of 69, Zheng Yi Sao passed away surrounded by her family, having never relinquished her glory and success as the most powerful pirate in history.

By Bertie Atkinson

Bertie Atkinson is a history writer at Malevus. He writes about diverse subjects in history, from ancient civilizations to world wars. In his free time, he enjoys reading, watching Netflix, and playing chess.