Who was the greatest pirate in history? Blackbeard? Captain Kidd? Jean Lafitte? None of them come close to the exploits of Ching Shih, aka Zheng Sao, Hsi Kai, or Shi Yang, depending on the historical source. She terrorized the South China Seas in the first half of the 1800’s–a time when Chinese women had few if any freedoms. Nevertheless, within the brutal world of pirates, Ching commanded ships and fought shoulder-to-shoulder with her male counterparts.
She was unquestionably the greatest pirate who ever lived. She pirated longer and garnered more wealth than any of her rivals. At the end of her career, she surrendered of her own free will, got to keep much of her loot, and live out the rest of her days in opulent freedom. How did a nineteenth century woman manage such amazing achievements?
Before she ruled as pirate queen, Ching Shih had a much humbler start to life. She was born Shi Yang into a Tanka family. They were a large clan who worked and lived on Chinese junks along the China coast. As a young woman, she worked in the brothels, gambling houses, and sailing boats of Guangdong province.
By 1800, Ching Shih was a ‘Madame’ working on a large floating brothel in the city of Canton. She made sure she caught the eye of Cheng Yi, a fearsome pirate who operated in the South China Sea during the Qing dynasty. After a brief courtship, he married the 26-year-old woman in 1801. Ching’s new husband was the formidable commander of the Red Flag pirate ships. He’d managed to unite many rival Chinese pirate crews into one.
Another story goes that it was Cheng Yi who sought his bride out due to her reputation as a shrewd businesswoman. Ching Shih used the secrets she learned as a brothel Madame to wield influence over her wealthy clients. She supposedly demanded equal control of the pirate fleet as a condition of their marriage. Ching Shih’s business savvy was certainly on display over the course of her career. She soon became his equal partner in building an even larger pirate fleet.
Cheng Yi’s pirate fleet became a true armada under their shared command.
The first year after being wed, pirating life carried on business as usual. That all changed in 1802, when Cheng’s pirate cousin was killed by the Vietnamese. Cheng Yi had to quickly consolidate power over his cousin’s fleet. Thanks to Ching Shih’s shrewd negotiating skills, the infighting among the pirates was short-lived. She helped negotiate a truce among the leaders of the pirate fleets, forming one confederation. Six fleets, each flying different flags would now operate as a united pirate navy, the Red Flag Fleet. By 1806, every seagoing vessel in the region paid tribute to them for protection.
The pirating business boomed until 1807, when Cheng was killed suddenly during a typhoon at age 42. Some some accounts say he was murdered. Regardless of the circumstances, his death left Ching Shih in a precarious position. The pirate king was gone. It was time for his widow to make her move and take full control. There was only one obstacle in her way.
Cheng Yi had an adopted son, Cheung Po Tsai, who was supposed to inherit his father’s command. Unlike in the West, adoption was often practiced in China to establish kinship, purely for business purposes. So Cheng’s adoption of a teenage fisherman as a son was not unusual. Cheung Po Tsai, however, was more than just Cheng Yi’s adopted on. The handsome young fisherman was rumored to also have been his lover!
Within weeks of Cheng Yi’s death, Ching Shih had taken Cheung Po to bed as her lover as well. She eventually married him! With this second wedding, she managed to maneuver herself into absolute control of the Red Flag Fleet. To avoid any succession struggles, she appointing her adopted stepson/husband as her second in command.
As a woman in command of a huge pirate fleet though, Ching Shih had her work cut out for her. Pirate ships had few if any women on board. Unlike in the Atlantic though, in the South Pacific, there was no stigma or bad luck attached to women being on board. Nevertheless, it wouldn’t have been easy for anyone, much less a pirate’s widow, to control so many blood-thirsty, treasure-craving outlaws.
Following Cheng Yi’s death, she now commanded over 1,500 pirate ships, and an estimated 70,000 men. In comparison, the famed Blackbeard commanded but four ships and 300 pirates. She was now formally known Ching Shih, “Cheng’s widow.” The legacy she would leave behind far exceeded that of her husband’s.
Her first act was to implement a Pirate Code.
It ensured strict discipline amongst the fleet, victories in battle, and riches from stolen loot:
- Only Ching Shih authorized any attack. Unsanctioned attacks or disobeying her orders was punished by beheading.
- Loot was to be gathered by officers and distributed equally. Repeat offenders to the rule were beheaded.
- Deserters ears were cut off when captured. Upon the second offense. they were beheaded.
- Rape was not tolerated and punished by, you guessed it, beheading.
- Consensual sex, without Ching Shih’s permission first, also meant a beheading for both.
- Pirates had to marry female prisoners before sex. Cheating or treating your new wife poorly was punished by beheadings.
The code was particularly noteworthy in its laws regarding the fair treatment of women. Whatever her captains thought about her personally, it was clear that the pirates respected and obeyed her authority.
The Red Flag Fleet routinely raided coastal villages and kidnapped foreign officials for ransom. A British East India Company employee named Richard Glasspoole was captured by Ching Shih’s pirates in 1809 and held for a months. By his account, he estimated that there were 80,000 pirates under Ching Shih’s command, and some 1,000 large junks and 800 smaller junks. It was through his accounts that we know much of anything about her vast operation.
So at the height of her success, Ching Shih controlled around 1,800 ships and more than 80,000 men, organized in six fleets, each with its own flag and commander. Her fleets attacked ships of all kinds, from small traders to imperial war ships, and ran a lucrative protection racket along the coast.
In 1808, the Chinese Qing Dynasty had to do something about the pirate situation in the South China Sea. They decided to bring down the worst of them all – the Red Flag Fleet and Ching Shih, a thorn in their side for years. The Qing gathered a massive fleet of naval warships and set a trap for them.
Rather than run, outnumbered, for a safe harbor, the bold Ching Shih instead sailed right at them. The pirates defeated a 35-ship naval flotilla off the coast of Shenzhen. When the smoke of the intense sea battle cleared, the Red Flag Fleet left behind a graveyard of burning, sinking ships. She even claimed a few dozen undamaged Qing ships as booty.
When confronted with a such massive enemy fleet, most pirates in the Caribbean Sea would have run, hiding in some island port. But Ching Shih was anything but your standard Caribbean pirate. Pirates like Blackbeard or Captain Kidd could boast a handful of ships and hundreds of men. She Shih commanded an entire pirate armada, with more sailors than most nations could muster.
Ching Shih was not intimidate by the Qing Imperial Navy.
A second Qing force attacked with 100 ships, half of navy, only to be sent packing as well. After two defeats, they asked their European allies for help. By 1809, Ching Shih was powerful enough to threaten the port city Canton (Guangzhou). The Chinese government leased the 20-gun British ship HMS Mercury and six Portuguese men-of-war. Big guns were not enough though to defeat the pirate queen’s fleet.
At the 1809 Battle of the Tiger’s Mouth, her Red Flag Fleet faced down a joint Chinese-Portuguese battle fleet that tried to trap her in Tung Chung Bay. For three months, the blockading Portuguese attempted to destroy her ships. Ching Shih took some heavy losses, but her fleet ultimately broke through and sailed away with her pirate force largely intact
Ching Shih realized the Qing attacks would never end with the help of huge foreign navies. She realized it was in her best interests to negotiate peace terms with the Chinese empire. After years of notoriety on the high seas, Ching Shih decided to retire in 1810. She waited until after the third battle, when her enemy was at its weakest. Then she used her considerable power to ask for a pardon for herself and her sailors.
She proved to be as effective at the bargaining table as she was in command. The Qing dynasty granted her pirates universal amnesty, the right to keep the wealth they had accumulated, and even jobs in China’s military. For herself, she negotiated a large cash settlement, a title of Chinese nobility (Lady Ching Shih!), and was even allowed to keep a small flotilla of ships and sailors.
Ching Shih retired (sort of) in Canton, where she reportedly lived out a peaceful life in an opulent mansion. Though she still kept an infamous gambling house going in the city. Ching Shih died in 1844, of unknown causes at the age of 69, a long life for anyone of that era.
She died widely respected annd remembered for her infamous exploits on the South China Sea. Compare her successful end to that of the pirate Blackbeard – cornered, murdered and beheaded by a British warship. Ching’s legacy even lasted through till modern popular culture came about. She inspired a memorable character in the Johnny Depp Pirates of the Caribbean movie franchise: Mistress Ching, one of the nine Pirate Lords.
The real Ching Shih, aka Hsi Kai, Zheng Sao, or Shi Yang was not fiction though. At the height of her power, she commanded a fleet capable of taking on a Chinese dynasty and any maritime force in the South Pacific. A truly remarkable feat for a 19th century woman. Though Ching Shih’s life may have begun in poverty and prostitution, it ultimately ended in fame and prosperity.