Ching Shih, one of the most successful pirates of all time, broke many barriers. Not only did she unite an ocean of battling pirates, secure riches and safety for hundreds of them, and outsmart several major powers at the time, including the Chinese government and the Portuguese Empire, but she accomplished all that despite being one of the few women to ever take on such a role.

Ching Shih’s background

Ching Shih was born in 1775 to humble origins in Guangdong, China during the Qing Dynasty’s rule. At a very young age, she began working as a prostitute in a floating brothel in the city of Canton. There, she had a reputation for using the secrets she learned at her job to wield power over wealthy and politically connected clients.

This was also where she first met Zheng Yi, a well-known and feared pirate. Though Ching Shih was just 15 years old at the time, the myth says that Zheng Yi took an immediate fancy to her due to her sharp wit. Less than a year later, the two of them married – a union Ching Shih only agreed to on the condition that she would receive equal control over his pirate fleet. Their subordinate pirates unanimously accepted her as their leader, as they lived on the fringe of traditional society, where gender roles were not enforced.

With Zheng Yi

After her marriage to Zheng Yi in 1801, Ching Shih was known as “Zheng Yi Sao,” meaning “wife of Zheng Yi.” Together, the couple ruled over 400 junks and between 40,000 to 60,000 pirates.

During their governance, a period of infighting plagued the pirates in the South China Sea. Zheng Yi Sao, a masterful diplomat and organizer, helped her husband unite the pirates with a confederation. By entering this organization, each pirate leader agreed to sacrifice some of his autonomy for the greater good. Every fleet had its own flag color to make it distinguishable to both other pirates and outsiders. Zheng Yi and Zheng Yi Sao commanded the largest and most powerful fleet of the confederation, the Red Flag Fleet.

In 1807, Zheng Yi died, presumably because he fell overboard the ship and drowned, though some sources claim he was murdered in Vietnam.

After Zheng Yi

After the death of her husband, Zheng Yi Sao became “Ching Shih,” which means “Zheng’s widow.” She ruled the confederation with the support of Zheng Yi’s adopted son, Zhang Bao, with whom she became romantically involved with. Ching Shih handled organizational matters related to the confederation, while Zhang Bao became the official commander of the Red Flag Fleet. However, many speculated that Ching Shih pulled the strings in all aspects of the couple’s rule. A government official who led negotiations with the pirates reported: “Zhang Bao obeyed [Ching Shih’s] orders and consulted her on all things before acting.”

Ching Shih and Zhang Bao created strict rules for the pirates in the confederation to follow. This law forbade pirates from harming allied villagers, raping captive women, or cheating on their wives. Furthermore, any goods taken by a fleet had to be presented for group inspection. The original seizer then received 20% of the riches. The rest went to a public fund, mainly used for repairs. Breaking these rules resulted in immediate execution.

Since the Qing Dynasty had neglected maritime law for decades, the pirate confederation gained power quickly. At its prime, Ching Shih commanded over 1,800 pirate ships and roughly 80,000 men. In comparison, the famous Blackbeard commanded just four ships and 300 men in the same century.

Battle at Tung Chung Bay

Ching Shih’s most famous battle was the one at Tung Chung Bay in 1809.

That year, the Red Flag Fleet had captured the Portuguese governor of Timor. In response, the Portuguese Empire agreed to help China in its battle against the pirates of the South China Sea. A few months later, 93 Chinese and six Portuguese ships blockaded Ching Shih and Zhang Bao’s fleet, which had docked at Tung Chung Bay for repairs. Due to unfavorable wind conditions, the pirates’ attempts at counterattacking or breaking the blockade were thwarted.

The situation turned to a stalemate, neither side willing to back down. Frustrated by their lack of progress, the provincial leader converted 43 junks into fireships and sent them towards the pirates. However, the Red Flag Fleet managed to divert them and tow them to shore, where they could extinguish them. Amid all this, the wind changed and blew two fireships back to the provincial fleets, igniting them instead. Ching Shih and Zhang Bao made use of this change in luck. They broke the blockade and escaped to sea with their men.

This was an embarrassment for the provincial fleet, which lost three ships and 74 men. Only 40 pirates died, on the other hand, and Ching Shih and Zhang Bao kept all their junks. Under Ching Shih’s rule, the Red Flag Fleet remained undefeated.


Frightened and angry at the pirates’ domination over the sea, the Chinese government started actively cutting off the pirates’ supply lines and had 60 provincial warships, as well as one British ship, patrol the waters. Meanwhile, the confederation began to crumble, as it had reached an organizational limit.

Her deeds catching up to her, Ching Shih decided to negotiate a deal with the dynasty in 1810. Her talks allowed for her and Zhang Bao to retain a substantial fleet, all their treasures, and avoid persecution. The dynasty agreed to give her men the opportunity to find governmental positions and did not punish them for their past actions.

At the time of her surrender on April 20, 1810, Ching Shih personally commanded 24 ships and over 1,400 pirates. Zhang Bao was offered the rank of lieutenant and the couple kept a private fleet of 20 to 30 ships.

Ching Shih chose to see her men off to a position of strength and wealth while she still held power, instead of opting to fight and have them be captured and killed.

Life after piracy

Zhang Bao and Ching Shih had a son together in 1813, whom they named Zhang Yulin. In 1822, Zhang Bao died at 36 years old while serving as a colonel.

After her second husband’s death, Ching Shih invested in the salt trade and opened a gambling house that also served as a brothel. Occasionally, she worked as a military advisor. She died in 1844, approximately 68 years old, having lived a relatively peaceful and prosperous life since the end of her career in piracy.  

A woman in men’s spaces

Ching Shih lived a pirate’s life, doing many things we would nowadays consider questionable at best. However, her care for her people, her wit, and her determination are undeniable. A crime boss who reversed gender norms, she built her own career and, despite her surrender, never faced defeat. In some ways, a role model.

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