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The Greatest Pirate Who Ever Lived

Beardless, brilliant and Chinese, she is history's most successful pirate. That's right: she.


The Greatest Pirate Who Ever Lived

Beardless, brilliant and Chinese, she is history's most successful pirate. That's right: she.


In 1801, a pirate named Zheng Yi was busy raiding Canton. Aside from the prerequisite plundering and rum-drinking, he had given his men one specific order: to break into a local brothel and bring him a prostitute by the surname of Shi.

Contemporary depiction of Zheng Yi’s proposal…possibly

One might expect a sinister fate to have awaited Ms. Shi upon her deliverance to the pirate captain (rape, swiftly followed by murder, being the most obvious). In actuality, Zheng Yi’s intentions were considerably more gentlemanly.

He intended to marry her. And recognizing that her current career prospects were rather limited, Shi accepted.

But though history would remember her simply as Zheng Yi Sao (郑一嫂), or “Zheng Yi’s wife,” this 26-year-old woman didn’t intend on spending the rest of her days as some plundering pirate’s eye candy. She wanted to become a pirate as well, and she did—one of the greatest pirates to have ever lived.

Right from the get-go, Zheng Yi Sao displayed a staggering degree of cunning. She happily accepted Zheng Yi’s proposal, but only on the condition that he share his wealth and power with her, equally. Then, while her new husband went about his pirate duties—further plunder and rum-drinking, presumably—she focused on the business side of things. The result was that in six years, she had engineered an alliance between Zheng Yi and his former pirate rivals, amassed a force of some 1,500 ships (called the Red Flag Fleet), and created a swashbuckling empire that extended all the way from Korea to Malaysia.

Zheng Yi certainly knew how to pick ’em.

Unfortunately, Zheng Yi was killed in 1807 after a misunderstanding with a typhoon—unfortunate for him, but extremely fortunate for Zheng Yi Sao. Refusing to step aside like a good, diligent widow, Zheng Yi Sao took charge of the Red Flag Fleet, convinced her late husband’s first mate to support her, and swiftly set about making herself the most respected and/or feared individual in all the East.

If films, books, and video games have taught us anything, it’s that pirates were a rowdy bunch at the best of times, and their attitudes towards women were…less than progressive. Zheng Yi Sao was having none of that, and quickly established a new pirate code to keep her peg-legged men in line. Anyone who looted a town that had already paid tribute the pirates had their head cut off and was dumped in the ocean. Anyone caught, or even suspected, of stealing from the pirate treasury had their head cut off and was dumped in the ocean. Anyone who raped a female prisoner had their head cut off and was dumped in the ocean (there’s a pattern there somewhere).

Zheng Yi Sao, as she appears in Pirates of the Caribbean

Needless to say, Zheng Yi Sao was not messing around. Not all her laws were quite so decapitation-happy, though. Ugly female prisoners were to be set free, and when a crew member purchased one of the prettier captives, he had no choice but to marry her.

But if he was unfaithful to her…head cut off, dumped in the ocean.

After just one year leading her pirate hegemony, Zheng Yi Sao had formed one of the largest navies on the planet, with some 17,000 men under her command. Tributes extorted from merchants across the Chinese seas and the coastal towns between Macau and Canton swelled her treasury to staggering levels. Her power was so great that she became the de facto government of the region. No longer was she merely a pirate; she was an entire political entity.

Quite understandably, the reigning Qing emperor wasn’t too thrilled with Zheng Yi Sao’s ability to supplant his divine authority, so he commissioned an imperial navy to put an end to her eye-patched enterprises.

Zheng Yi Sao won, hands down.

Not only did she defeat the emperor’s forces, but she captured 63 of his ships and persuaded many of his men to join her. How did she persuade them? They were given a choice: join her crew and enjoy the complimentary rum, or be tied to the deck and be beaten to death. It was (assumedly) an easy decision to make.

Over the next two years, the Qing dynasty (1616-1911) kept up its offensive, even going so far as to hire the British and Portuguese navies to see Zheng’s fleets off. Those two nations were the superpowers of the time, totally unparalleled in their sea-faring prowess…and Zheng Yi Sao crushed them both. There was literally no stopping her.

A modern depiction of Zheng Yi Sao. Some artistic license taken.

But Zheng Yi Sao didn’t let her achievements go to her head. Sick and tired of constant defeat, in 1810 the Qing Emperor offered an amnesty for all pirates—if Zheng Yi Sao would agree to make peace. Recognizing that her good fortune would not last forever, Zheng Yi Sao went willingly to the negotiations table. She showed up unannounced at the home of the governor-general of Canton, convinced him to sign a treaty with her despite her gender, and secured quite possibly the most generous pension package ever.

Not only did she get her pardon, and a pardon for the majority of her men, but she kept ownership of all her treasure. Docking her ship for the last time, she promptly married her later husband’s first mate and, at the age of 35, retired to a life on the mainland, where she opened a gambling den and brothel.

She ran her new, less pirate-y business for the rest of her life, and by the time she died at the ripe old age of 69 (this was the 19th century; 69 was seriously good) she had become not only a living legend, but a mother and a grandmother too.

No doubt she had some interesting bedtime stories to tell her grandkids.

Illustration courtesy of Huang Shuo


For more historical conflict in China, try our blog on The Battle of Talas.

Looking for more incredible women? Have a look at Trung Trac, the hero of Vietnam, Pingyang Warrior Princess, or Badass Heroines from ancient China.

And for another historical bad-ass, read about Dian Wei, the dual-axe wielding bodyguard.