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Yes, Ching Shih (1775-1844), also known as Zheng Yi Sao, is widely regarded as the most successful pirate in history. She led the Red Flag Fleet in the South China Sea from 1801 to 1810, which was believed to be the largest pirate fleet ever known.

Ching Shih, which translates to “Cheng’s widow,” gained immense recognition beyond her husband’s name. After her husband’s passing, she took over his leadership role and commanded an astonishing fleet of over 1,800 pirate ships and approximately 80,000 crew members. To put it into perspective, even the notorious Blackbeard led a much smaller fleet of just four ships and around 300 pirates.

Ching’s husband, Cheng I, was a powerful leader who commanded the fearsome Red Flag Fleet of pirate ships. He successfully united various Chinese pirate groups. In 1801, Ching, then 26 years old, married Cheng and actively participated in his piratical endeavors.

After Cheng’s death, Ching, now she is known as Ching Shih, married his adopted son, who was expected to inherit his father’s leadership. With this union, Ching Shih took complete ownership of the Red Flag Fleet. Her first order of business was to establish a strict code of conduct to maintain discipline, ensure combat effectiveness, and maximize the plunder obtained from raids. Here are the main rules she enforced:

  • Only Ching Shih could authorize attacks. Unauthorized attacks resulted in severe punishment, often by beheading.
  • Loot had to be collected by designated leaders and distributed equally among the crew.
  • Deserters had their ears cut off for the first offense and were beheaded for a second offense.
  • Rape was strictly forbidden and punishable by beheading.
  • Consensual relations without Ching Shih’s permission led to beheading for both parties, with the female partner being thrown overboard.
  • Pirates were required to marry female captives before engaging in intimate relations. Mistreating or cheating on these spouses resulted in beheading.

In addition to extorting protection money from ships, Ching Shih’s fleet raided coastal villages and captured foreign officials for ransom. One such hostage, Richard Glasspoole, was held captive for four months, providing valuable insights into Ching Shih’s operations.

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