Cheng I Sao
At the height of her powers, Cheng I Sao commanded more than 300 pirate ships and an estimated 20,000 men. What’s more, she had good relations with fellow pirate leaders and between them, they had a huge outlaw armada at their disposal. Quite simply, Cheng I Sao was one of the most remarkable people ever to set sail under the Jolly Roger. And her accomplishments are even more astonishing given her humble origins.
Though next to nothing is known about Cheng’s early years, what is known is that she was born as Shi Xianggu, in Guangzhou, southern China, in 1775. As a young woman, she turned to prostitution but was hardly a victim. Using her charms, she quickly learned how to take advantage of men, getting to know their secrets and using this knowledge to her advantage. One of the men she got to know and win the respect of was Cheng I, a local businessman who belonged to a long line of pirates.
Whether it was pure love, or whether Cheng I saw the chance to make use of Shi Xianggu’s wiles for his own ends, the pair were soon married. The most profitable partnership in piracy history was born. For six years, the duo oversaw the expansion of the Cheng piracy empire, with his militaristic aptitude and her people skills ensuring that they controlled almost all the South China Sea. Then, in 1807, Cheng died. But, rather than stepping aside, his grieving wife took on the business herself. Cheng I Sao (literally translated as ‘Cheng’s Widow’) was born, and she was only getting started.
In a move worthy of a Roman emperor, Cheng installed her deceased husband’s number two, a man by the name of Chang Pao, as the head of her formidable navy. And while he took to the seas to plunder what he could get his hands on, she worked behind the scenes, building up alliances with other pirates and extending the business into other areas, including extortion and blackmail.
But perhaps Cheng’s most remarkable achievement was her creation of a set of pirate laws. Realizing she needed to instill some discipline into an armada that now stretched to 1,500 ships, she laid down her laws. Any sailor flying under her Red Flag would be beheaded for disobeying an order. Thieves would also lose their heads. What’s more, she also changed the rules with regard to captives. Women deemed too old or ugly were set free, while young and attractive females were auctioned off among the crews. Business was booming, but her list of enemies was growing.
With the Chinese Navy, as well as the British and the Portuguese on her tail, she quickly accepted a deal from her homeland: In exchange for her freedom, and that of most of her men, she would leave her piracy life behind. Remarkably, unlike so many pirates, Cheng lived to a fine age, becoming a grandmother and respected businesswoman. She even enjoyed a peaceful death, dying in her sleep at the age of 69 in 1844.