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Ching Shih — also known as Cheng I Sao — instilled fear in the hearts of merchants across the China Sea in the early 19th century. During her relatively short run as a pirate lord — only about a decade — this ruthless and cunning woman went from being a prostitute to commanding the famous “Red Flag Fleet” and sending hundreds of thousands of men into battle.
She was a prostitute in one of Canton’s floating brothels when pirates captured her at age 26. To her surprise, she was asked to marry one of them, Cheng Ch’i, who belonged to a long and famous dynasty of sea thieves. From then onwards, they were partners in bed and business. With her help, Cheng Ch’i managed to assemble one of the largest and most dangerous fleets in China.
Jacquotte Delahaye reportedly came from Saint-Domingue in present day Haiti, and was the daughter of a French father and a Haitian mother. Her mother is said to have died in childbirth. Her brother suffered from mild retardation, and was left in her care after her father's death.
According to legend and tradition, she became a pirate after the murder of her father. Jacquotte Delahaye is the subject of many legendary stories. To escape her pursuers, she faked her own death and took on a male alias, living as a man for many years. Upon her return, she became known as "back from the dead red" because of her striking red hair.
She led a gang of hundreds of pirates, and with their help took over a small Caribbean island in the year of 1656, which was called a "freeboter republic".  Several years later, she died in a shootout while defending it