The greatest pirate to ever live was an old pro. Ching Shih was working at a floating brothel in Shanghai when the heir to a pirate empire fell madly in love with her. He married her (it was consensual) and they ruled together for six years before her husband died doing pirate stuff, which is notoriously dangerous.
Ching Shih was born Shi Yang (aka Shi Xianggu) in 1775 in Xinhui, Guangdong. She was a Tanka, working as a prostitute on a floating brothel in Guangdong. She met her husband Zheng Yo, a well known pirate in 1802 at the age of 26. When she married him she was named Zheng Yi Sao (“wife of Zheng Yi”) by the people of Guangdong. But we’ll refer to her as Ching Shih. She was able to negotiate an equitable partnership, which was unusual at the time.
Zheng Yi, hailed from a family of well-known pirates whose roots traced back to the Ming dynasty. He abducted Zhang Bao, in 1798, and adopted him as his son at the age of 15, pressing him into service as a pirate. Ching Shih had two sons with Zheng Yi: Zheng Yingshi, who was born in 1803, and Zheng Xiongshi, who was born in 1807.
Together Ching Shih and Zheng Yi united the pirates in their region into a confederation in 1805. signed an agreement in which each pirate leader sacrificed some of their autonomy in exchange for being part of a much larger, and more powerful, group. The confederation consisted of six fleets known by the color of their flags – red, black, blue, white, yellow, and purple. Zheng Yi and Ching Shih commanded the biggest fleet in the confederation, the Red Flag Fleet. Thier fleet was composed of 400 ships and between 40,000 to 60,000 pirates.
In 1807, Zheng Yi died at the age of 42. Ching Shih quickly took over operations, with the support of his family and allies she had cultivated in the years she co-ruled with her husband. She was unanimously elected leader of the Red Flag Fleet. Most importantly, Ching Shih had the support of Zhang Bao, her husband’s adopted son, who was in effect commanding the Red Flag Fleet at the time.
According to documents that have survived Zhang Bao deferred to Ching Shih in all matters and respected her leadership. They began a romantic relationship. Together they faced the major naval powers of their age including the East India Company, the Portuguese, and Chinese Qing Navy
Her and her fleet were so successful that the Emperor of China offered her a retirement package-which is not a thing emperors or kings, or governors were keen to do for pirates in any age. The agreement was that she could live, keep everything that she stole AND her crew would be offered pardons and positions in the Chinese Navy if she stopped being a pirate.
In 1810, Zheng Yi Sao negotiated a surrender to the Qing authorities which allowed her and Zhang Bao to retain a substantial fleet and avoid prosecution. They married at the signing of the agreement which also gave them cover when they “bowed” to the emperor, which is conveniently also part of the marriage ceremony. At the time of her surrender, she personally commanded 24 ships and over 1,400 pirates.
After her retirement she ran a gambling house, which may have also dabbled in the oldest profession. Ching Shih died in 1844 at the age of about 68, having lived a relatively peaceful and prosperous life as one of the most successful pirates in history. Western historians didn’t believe the stories about her her until feminist scholars in 1986 reexamined the extensive and well documented evidence of her legacy.