Mrs. Cheng: The Most Successful Pirate in History

Mrs. Cheng, Ching Shih attacking pirates
Mrs. Cheng (on the right) goes on the attack. Wikimedia Commons

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History's most successful — and feared — pirate fleets shared some key attributes. They were well-oiled operations that enforced strict rules, despite the lawlessness of their profession. Crucially, a lot of them were helmed by intelligent leaders who played politics, exercised diplomacy as needed and earned the respect of their peers.

One exceptionally skilled fleet commander terrorized the South China Sea in the early 19th century. At the height of her power, she directed a vast coalition of several thousand pirates, the largest pirate crew ever assembled. Then, having made history in spectacular fashion, she retired from piracy and lived to a ripe old age.

Mrs. Cheng, aka Ching Shih

Who was this seafaring outlaw? Well, in contemporary, English-language books and websites, she's often called "Ching Shih." But that wasn't her real name. "Ching Shih" was the invention of "an early nineteenth century author who was endeavoring to render a Chinese text into English," says Dian Murray, a history professor at the University of Notre Dame and authority on China's pirate past.

"The lady pirate in question is most commonly referred to in the official Chinese sources simply as 'Mrs. Cheng' or 'Mrs. Zheng,'" Murray says via email. Those spellings came from two different romanization systems that are used to convert Mandarin Chinese characters into Latin letters. For consistency's sake, we'll use the name "Mrs. Cheng" in the remainder of this article.

Cheng's early life is poorly documented. We do know that she worked at a Cantonese brothel before she married one Cheng I in the year 1801 or so. (She was likely in her twenties at the time.)

A notorious pirate, Cheng I was the product of a changing seascape. From 1771 to 1802, Vietnam was embroiled in the Tay Son Rebellion, a peasant-led uprising against the Lê Dynasty. Lacking a strong naval force, the rebels contracted small-time pirates to fight and loot on their behalf. In exchange, the plunderers received weapons, vessels and, best of all, safe harbors.

Such allowances created an environment where organized, large-scale piracy could flourish — even after the rebellion was put down. In 1802, the South China Sea played host to roughly 50,000 pirates.

Red Flag, Black Flag

By 1804, Cheng I and his cunning wife had united five numerous fleets into one gigantic confederation made up of 70,000 men and 400 junks (large sailing vessels). The coalition was broken up into half a dozen semi-autonomous squadrons whose leaders were answerable to the Chengs. Each unit bore the name of a colored flag: There was a Red Flag Fleet, a Black Flag Fleet and so on.

One of sailors in this mighty criminal syndicate was Chang Pao, a teenager who'd been captured by Cheng I. "After recognizing his potential for leadership, Cheng I initiated Chang Pao into the pirate ranks by means of a homosexual liaison," Murray says.

Soon enough, Cheng I put the youth in command of his own junk and even adopted him as his own child.

But it was Mrs. Cheng who held the confederation together after Cheng I's abrupt death in November 1807. Taking charge of the enterprise, she implemented a new code of conduct. Under these rules, pirates in her fleets would get decapitated if they stole goods from a communal fund that was meant to benefit everyone. Likewise, raping a captive woman was punishable by execution.

The rules were co-authored by Chang Pao, who'd assumed a powerful new role within the outfit. "[Mrs. Cheng] realized that she needed a lieutenant to help her command the 300 junks and 20,000-40,000 men of what had previously been her husband's Red Flag Fleet," says Murray. Chang Pao took the job, becoming Mrs. Cheng's lover and later her second spouse.

Going Out on Top

For years, Mrs. Cheng maintained good relationships with the leaders of every fleet in the coalition. She ran a tight ship (so to speak) and oversaw everything from monetary transactions to religious ceremonies.

On her watch, the pirate alliance expanded like crazy. Of the 270 government-owned ships stationed at Tien-Pai, 266 fell under her control. By demanding regular patronage from sailing merchants, Mrs. Cheng's sailors profited off Canton's lucrative salt trade. As a matter of fact, the outlaws extracted so much revenue across their domain that Mrs. Cheng found it necessary to establish a network of land-based financial offices.

Her strategic mind was well-suited to warfare. Mrs. Cheng's fleets regularly embarrassed the navies of southern China. They grew notorious for kidnapping Chinese officials, blockading rivers and routing just about anybody who opposed their will. But that was to change.

In 1809, China's increasingly agitated government borrowed well-armed vessels from the British East India Company and the Portuguese Navy. At the same time, it also offered amnesty to pirates who surrendered.

"The offer was tempting to the leader of the Black Flag Fleet, who then forced a confrontation with the Red Flag Fleet," Murray says. While negotiating with the government, he turned over the captives from that inter-squadron battle as a gesture of goodwill. Before long, other units were defecting from Mrs. Cheng's confederation.

She could read the writing on the wall. Blackbeard and other career pirates who kept plundering until the bitter end usually met horrible deaths, whether on the high seas or at the gallows. Mrs. Cheng decided to go a different route.

On April 8, 1810 — after an earlier round of peace talks failed — she took a delegation of 17 pirate wives and children to the governor-general's office in Canton. Inside, Mrs. Cheng brokered a favorable amnesty deal. "[Chang Pao] was allowed to retain between 20-30 of his vessels for use in the salt trade and received an appointment in the Chinese water forces," Murray tells us. Most of the pirates who'd served under her were granted pardons as well.

Chang Pao passed away in 1822 at 36. He was survived by his brilliant wife, who died peacefully in 1844 at the age of 69.