If asked who the most successful pirate was, most people would say Black Beard. While Black Beard achieved great fame and fortune, Ching Shih is the name of the most successful pirate in history. What is even more incredible is that Ching Shih was a woman—and a very attractive woman to boot, and she was very smart. Born into poverty in the Guangdong province of China in 1775, she worked as a prostitute in a floating brothel in Canton at a very young age. A pirate named Zheng Yi, who it is believed was a client of Ching Shih. It was said she was his favorite prostitute. One day, Zeng Yi decided to send a raiding party to the brothel. He also instructed his men to bring back with them, in addition to money and treasure, the prostitute Ching Shih.
Ironically, Zeng Yi proposed marriage to his captive and she accepted. Ching Shis agreed to Zheng Yi’s proposal of marriage with the condition that she would work side by side with Zheng Yi and share in the profits from their piracy. The organization was called the Red Flag Fleet, which, under Zheng Yi, numbered some 200 ships. Once Ching Shih got involved, the fleet grew to 600 ships. The couple formed the Cantonese Pirate Coalition, another pirate named Wu Shi’er. When Zhen Yi died in 1807, they had 1700-1800 ships in the Red Flag Fleet with crews totaling 70,000 pirates.
Edward Carrington, the American Consul in Canton, China, wrote to President James Madison on April 19, 1807 the following.
The Coast of China and particularly, the entrances to this port have for a long time been infested by Chinese ladrones or pirates, in very alarming and considerable forces. Hitherto they have only succeeded in capturing China and Macao merchant vessels, and small boats; a short time since an English ship, which had been on shore at Macao for a pilot, in returning onboard the ship, in Macao roads, was captured by one of these pirates. The officer and crew are now prisoners and will not be liberated without ransom.
In her book Pirate Queen (Boundwood Books publisher, groundwoodbooks.com), Helaine Becker describes how a former prostitute became a Pirate Queen. After her husband’s death, his adopted son Chang Pao took over the command. Chang Pao was also in a homosexual relationship with Zhen Yi. Interestingly, historians say this was not an unusual relationship in those times. Chang Pao was most likely not up to the job and more interested in fashion than leadership. He soon opted to allow Ching Shih to take command of the Red Star Fleet. In no time, Ching Shih created strict rules and regulations. She instituted a pirate government where pirates had a say in governing the fleet. One rule was that any plunder that was stolen by any pirates had to be brought to the ad hock fleet government before any pirate took his share. As head of the fleet, Ching Shih took 20% of the treasure. The pirate received 80%. Ching Shih’s rules stipulated that unfaithfulness and rape were offenses punishable by death. Flogging, quartering, and being put in irons were other punishments. If a pirate deserted, he would be hunted, and when found, his ears would be cut off. Any person who opposed Ching Shih would have their feet nailed to the deck while they were beaten. If a captive was an ugly woman, she would be safely returned. If the captive was attractive, any fleet member was allowed to take her as his wife. However, the pirate was duty-bound to be faithful to his wife.
In his book, “Narrative of his captivity and treatment amongst the Ladrones” (first published in George Wilkinson’s Sketches of Chinese Customs and Manners, Bath, 1814.) Richard Glasspoole writes about his captivity after being captured by the pirates of the Red Star Fleet. Glasspoole explained that he was imprisoned for two months in the rat-infested hold of the pirate ship. Those who put up any resistance faced torture or execution if captured. European mariners fared slightly better since they could be ransomed, but this was not a quick process, and so many were kept in cramped and filthy conditions for months. One such sailor, the fourth officer on the captured Marquis of Ely, described how he was kept in the rat-infested hold of a ship of Zheng Yi Sao’s pirates for four months, during which time he was obliged to survive on caterpillars and rice. As reported by Mark Cartright in November 2021, in the World History Encyclopedia.
“Officer Glasspoole also describes the operations of the pirates. Those Chinese captured were given the stark choice of joining the pirates or being flogged to death. Captured European mariners were forced to assist in attacks on villages, where the pirates collected the heads of their victims, tying pairs together using their pigtails and wearing them around their necks as gruesome trophies. Glasspoole’s gunnery skills meant that he was used by Zheng Yi Sao to operate cannons. The Englishman seems to have become a favorite of the pirate chief as, believing it would ward off any chances of injury, she was said to have sprinkled garlic water over him before each battle.”
After his release, Glasspool wrote a letter to the captain of the Marquis of Ely.
“I am sorry to inform you that this morning myself with the cutter’s crew were made prisoners by a large ladrone boat mounting 20 guns they say if you will send 100,000 dollars ransom they will send us to Macao or they say they will behead us, be so good as to write me and say what you can give, I think they will take much less; offer 20 or 30 thousand, send immediately an answer for God’s sake an answer by this boat that brings this what can be given, the man that brings us knows where to find us, I will send you the head man’s answer, though if you send the dollars he will give us a chop to pass to Macao. I trust this will be legible we anxiously expect an answer.”
R. Glasspoole, 4th Mate and 6 Men. Address to Captain Kay.
Thursday, 21st September. (excerpted from Captured by Pirates by Cindy Vallar, www.cindyvallar.com
The Red Fleet’s raids were not limited to ships. There were numerous reports of raids on coastal villages from Macau to Canton. Shih would sometimes extract a tax on the village and collect it regularly. Her pirates were fierce in their raids. China, Portugal, and Britain’s navies could not defeat her pirates. Some stories claim Ching Shih was also an opium smuggler.
Ching Shi was so skilled at running her pirate enterprise that she was undefeated by the official Zhang Bat Ling, the agency charged with dealing with piracy in China was deadlocked. Then suddenly, one day Ching Shih, most likely sensing that the end of her reign was nearing, unarmed, and accompanied by 17 illiterate women and children, walked boldly into the office of Zhang Bat Ling. Shih offered a negotiable end to her career as a pirate, provided she was able to keep her riches and be free. Ching Shih walked out free and then married Chang Pao, with whom she gave birth to a son. When her second husband, Chang Pao, died, she moved to Canton and opened a gambling house, which she operated until she died in 1844.