Madame Ching or Ching Shih also known as Cheng I Sao, was a prominent pirate in middle Qing China, who terrorized the China Sea in the early 19th century. She personally commanded over 300 junks manned by 20,000 to 40,000 pirates —men, women, and even children. She entered into conflict with the existing empires of the time, such as the British Empire, the Portuguese Empire, and the Qing dynasty. She was one of the few pirate captains to retire from piracy and is considered to be the most successful pirate in history.
She married Cheng I who belonged to a family of successful pirates who traced their criminal origins back to the mid-seventeenth century. Following his marriage to Ching Shih, “who participated fully in her husband’s piracy”, Cheng I used military assertion and his reputation to consolidate a coalition of competing Cantonese pirate fleets into an alliance. By 1804, this coalition was a formidable force, and one of the most powerful pirate fleets in all of China; by this time they were known as the Red Flag Fleet.
On 16 November 1807, Cheng I died in Vietnam. Ching Shih immediately began maneuvering her way into his leadership position. She started to cultivate personal relationships to get rivals to recognize her status and solidify her authority. In order to stop her rivals before open conflict erupted, she sought the support of the most powerful members of her husband’s family: his nephew Cheng Pao-yang and his cousin’s son Cheng Ch’i. Then she drew on the coalition formed by her husband by building upon some of the fleet captains’ existing loyalties to her husband and making herself essential to the remaining captains.
Since Ching Shih would have such a large force at her command, she knew she needed someone to assist her in managing the Red Flag Fleet’s day-to-day operations, but remain loyal to her and be accepted by the low-level pirates. She believed there was only one man for the job, Cheung Po Tsai.
Finally, in late 1809 and early 1810, her fleet suffered a series of defeats inflicted by the Portuguese Navy at the Battle of the Tiger’s Mouth, upon which she accepted an amnesty offered by the Chinese government to all pirates who agreed to surrender, ending her career that same year. She kept her loot and opened a gambling house.
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In 1810 she ended up meeting Lady Blossom, who told her about a new chance at life. Like the pirate she was, she took it.