The most successful pirate of all time - Dian Murray

At the height of their power,

infamous Caribbean pirates like Blackbeard and Henry Morgan

commanded as many as ten ships and several hundred men.

But their stories pale next to the most successful pirate of all time.

Madame Zheng commanded 1800 vessels,

made enemies of several empires,

and still lived to old age.

Madame Zheng began her life as a commoner

working on one of the many floating brothels, or flower boats,

in the port city of Guangzhou.

By 1801, she had attracted the attention

of a local pirate captain named Zheng Yi, and the two soon married.

Guangzhou’s fishermen had long engaged in small-scale piracy

to supplement their meager incomes in the offseason.

But a successful peasant uprising in neighboring Vietnam

at the end of the 18th century had raised the stakes.

The victorious Tây Sơn rebels had unified their country

only to face a Chinese invasion

and ongoing maritime battles with the Vietnamese rulers they had overthrown.

So they commissioned Guangzhou’s pirates to raid the coast

and join the fight against their enemies.

Serving their Vietnamese patrons turned the Zhengs and other pirates

from ragtag gangs aboard single vessels

into professional privateer fleets

with dozens of ships able to hold their own at sea.

In 1802, the Tây Sơn were overthrown

and the pirates lost their safe harbor in Vietnam.

But instead of scattering,

the Zhengs met the crisis by uniting the rival Cantonese pirate groups

into a formidable alliance.

At its height, the confederation included 70,000 sailors

with 800 large junks

and nearly 1,000 smaller vessels.

Those were organized into six fleets marked by different colored flags.

The Zhengs were unlike many other historically-known privateers,

such as Henry Morgan or Barbarossa,

who acted on behalf of various naval powers.

Instead, the Zhengs were now true outlaws,

operating without support or approval from any government.

Zheng Yi met an untimely end in 1807,

but his widow didn’t hesitate to secure their gains.

Through skillful diplomacy,

Madame Zheng took charge of the confederation,

convincing the captains that their best interests lay in continued collaboration.

Meanwhile, she appointed Zhang Bao, the young protege of her late husband,

as the commander of her most powerful squadron, the Red Flag Fleet.

Zhang became not only her right-hand man, but her lover and, soon, her new husband.

Madame Zheng consolidated her power through strict military discipline

combined with a surprisingly progressive code of laws.

Female captives were theoretically protected from sexual assault,

and while pirates could take them as wives,

mistreatment or infidelity towards them was punishable by death.

Under Madame Zheng’s leadership,

the pirates greatly increased their power,

with 200 cannons and 1300 guns in the Red Flag Fleet alone.

Within a few years, they destroyed 63 of Guangdong Province’s 135 military vessels,

forcing their commanders to hire more than 30 private junks.

Madame Zheng was so feared that Chinese commanders charged with apprehending her

spent most of their time ashore,

sometimes sabotaging their own vessels to avoid battle at sea.

With little to stop them,

the pirates were able to mount successful —and often brutal—

raids on garrisons, villages, and markets throughout the coast.

Using her administrative talents,

Madame Zheng established financial offices in cities and villages,

allowing her pirates to extract regular protection payments on land and sea alike.

This effectively created a state within a state

whose influence reached far beyond the South China Sea.

At the peak of her power,

Madame Zheng’s confederation drove five American schooners

to safe harbor near Macao,

captured a Portuguese brig,

and blockaded a tribute mission from Thailand

—all in a single day.

But perhaps Madame Zheng’s greatest success lay in knowing when to quit.

By 1810, increasing tension between the Red and Black Flag Fleets

weakened the confederation from within

and rendered it more vulnerable to attack from without.

So, when the Chinese government, desperate to stop the raids,

offered amnesty in exchange for the pirates’ surrender,

Madame Zheng and Zhang Bao agreed, but only on their own terms.

Their confederation was successfully and peacefully dismantled in April 1810,

while Zhang Bao was allowed to retain 120 junks for personal use

and became an officer in the Chinese navy.

Now fighting pirates himself,

Zhang Bao quickly rose through the ranks of military command,

and Madame Zheng enjoyed all the privileges of her husband’s status.

After Zhang Bao died in 1822,

Madame Zheng returned with their eleven-year-old son to Guangzhou,

where she opened a gambling house and quietly lived off the proceeds.

She died at the age of 69—an uncommonly peaceful end to a pirate’s life.