When most of us think of “pirates” we think of buccaneers like Blackbeard and Captain Morgan who raided shipping in the Caribbean in the 17th and 18th centuries. But the most successful pirate in history was a woman who commanded a huge fleet on the coast of China in the early 1800s.
In the last years of the 18th century, China was a pirate’s haven. The Imperial Government in Beijing was weak and powerless, dominated by foreigners. The thriving overseas trade meant a constant flow of ships to Europe and the American west coast, carrying silk, tea, opium, and money.
One of the pirates plundering ships off the Chinese coast was Zheng Yi, who commanded a group of ships known as the Red Flag Fleet. In 1801, Zheng Yi captured a ship in the harbor at Canton which was operating as a floating brothel. The business was being run by a young woman who had begun as an ordinary sex worker and had steadily worked her way up to become the madam, where her management skills became apparent. According to one version of the later legends, Zheng Yi became infatuated with her and captured the ship specifically to take her captive and marry her; in another version, he had heard about her shrewd business skills and proposed marriage to her. She agreed, on condition that she be given a share in the pirate loot and financial control over the pirate business. We do not know her real name, but she subsequently became known simply as Zheng Yi Sao (“Zheng Yi’s wife”).
The Red Flag Fleet grew steadily. Zheng Yi and his wife negotiated a confederation with another Cantonese pirate, Wu Shi, and together they had some 600 ships under their command. (By comparison, the most famous Caribbean pirate, Blackbeard, never had more than four ships in his fleet.) In one of their raids, the Red Flags captured a 15-year old boy named Chang Pao, who then joined the pirate fleet, was adopted by Zheng Yi, and rose to become second-in-command.
In November 1806, Zheng Yi died. In some accounts, he was killed in a storm at sea, and by other stories he was murdered by rival pirates from Vietnam. And it was now that Zheng Yi Sai stepped in. She had already been running the financial side of the Red Flag Fleet, arranging the distribution of loot. Now, she took over command as well: taking Chang Pao as her lover, she became the de facto leader.
Her first order of business was to expand the “business”. Instead of just attacking passing ships, Zheng Yi Sao turned the pirate fleet into an organized crime ring: she began extorting protection money from coastal villages and taking over gambling houses, opium dens and brothels, and soon began to act as almost a provincial governor, collecting “taxes” and setting up partnerships with farmers to supply food for her pirate crews. She also had an extensive spy network that extended right into the imperial court. Through alliances with other pirates, she expanded the Red Flag Fleet to 1,600 ships with 80,000 crew members and supporters on shore.
To keep discipline in her organization, she issued a set of codes. Each pirate captain could keep 20% of all the loot he captured, but the rest had to be turned over to a central pot which was used to finance the organization. Individual pirates were provided with health care and were compensated in case of injury—there were even retirement benefits. Anyone who disobeyed the orders of a superior was beheaded: anyone who tried to cheat by withholding treasure had his ears cut off and was beheaded at the second offense. Prisoners were to be treated with respect: any pirate who raped a captive was executed, and even if there was consensual sex with a captive, both would be killed.
Within a few years, Zheng Yi Sao’s organization controlled much of Guangdong Province, and her Red Flag Fleet dominated the entire South China Sea. Any ship, Chinese or foreign, that sailed through her territory had to pay a “tax” or risk attack.
When the Imperial Government tried to put an end to the pirate menace, Zheng Yi Sao proved herself to be a capable military commander. The admiral Kwo Lang was dispatched in 1808 to destroy her fleet, but instead she outmaneuvered and defeated him, and captured 63 of his ships (most of which then joined the pirates). Kwo Lang committed suicide. Over the next year, other fleets were dispatched by the Portuguese and the Dutch, but they too were beaten. One of the ships that the Red Flag Fleet captured was the Marquis of Ely, from the British East India Company, and the written story from one of the officers on this ship who was held for several months, named Richard Glasspoole, is one of the few first-person accounts from the time of Zheng Yi Sao. A year later the town of Sanshan sent a fleet against Zheng, and she retaliated by invading the village and beheading all its male inhabitants.
Then in 1810 the Red Flag Fleet suffered some reverses. The Portuguese Navy defeated a part of Zheng’s forces at the Battle of the Tiger’s Mouth, and she also faced a growing threat from the rival Black Flag pirate fleet. When the Imperial Chinese Government announced an amnesty in April 1810, Zheng Yi Sao decided to get out of the piracy business. Presenting herself to the Governor at Canton, she negotiated a deal in which her fleet would disband and she would retire; in exchange, 126 of her pirates would be executed by the Governor, another 200 would be banished from China, and the remaining 18,000 would be pardoned. They would all be allowed to keep their money, and those who wished would be taken into the Imperial Army. Zheng Yi Sao also asked the Governor to legally annul the adoption of Chang Pao by Zheng Yi, which permitted her to then marry him. She also became a “Lady By Decree” and a minor member of the nobility.
Zheng Yi Sao lived out the rest of her days as the manager of a gambling house in Guangzhou. She died in 1844.
When Disney Studios released the third movie in its “Pirates of the Caribbean” franchise, the pirate queen Zheng Yi Sao got a cinematic nod: one of the fictional “Nine Pirate Lords” in the movie was a female Chinese pirate called “Mistress Ching”.
Hidden History 
Fascinating stuff! Interesting how, when governments fail or become weak, criminals sometimes step in, and how often they do so in semi-benign manner. As I recall Pablo Escobar was not considered a villain by a very substantial number of the poor who benefited from his business and generosity.
John Gotti was also well-liked in his neighborhood, as he gave away a lot of money and paid for local sports teams and such.