Skip to main content
/living
  Edition: U.S. | Arabic | Set Pref
  • E-mail
  • Save
  • Print

Most successful pirate was beautiful and tough

  • Story Highlights
  • Most successful pirate of all time was former prostitute Cheng I Sao
  • Her code of conduct was harsher than other pirate laws
  • Disobeying or stealing could cost you your head
  • Pirates who bought pretty captives as wives risked death for adultery
  • Next Article in Living »
By Maggie Koerth
Decrease font Decrease font
Enlarge font Enlarge font
Mental Floss

(Mental Floss) -- You can keep your Bluebeards and your Blackbeards. The most successful pirate of all time controlled a fleet of more than 1,500 ships and upwards of 80,000 sailors -- and she did it all without the help of facial hair.

art.tall.ship.afp.gi.jpg

Tall ships like the La Boudeuse used to face threats from pirates as they sailed around the world.

When a Chinese pirate captain named Cheng married a beautiful prostitute in 1801, he wasn't just getting the girl of his dreams; he was making the best financial investment of his career. His new bride, known to history as Cheng I Sao, or "Wife of Cheng," agreed to the marriage on one condition -- that she would share equally in his power and would be given the opportunity to help him secure more wealth.

Sounded like a deal to Cheng, and for the next six years, the husband and wife teamed up to grow their piracy business along the coast of the South China Sea, as far south as Malaysia. But then, in 1807, Cheng passed away. Instead of stepping aside like a "proper" widow, Cheng I Sao promptly took the reins.

Thinking outside the treasure box

Although clearly ahead of her time, Cheng I Sao was shrewd enough to realize that the pirate masses weren't likely as enlightened. So, her first act as leader was to make her husband's second-in-command, Chang Pao, official captain of the fleet.

While Chang Pao led the men into battle, Cheng I Sao focused her attention on business, military strategy, and the enormous task of governing a growing body of ruffians. In the years following her husband's death, she steadily brought more and more outlaws under the banner of her Red Flag Fleet.

In fact, Cheng I Sao was eventually responsible for nearly all the piracy in the region and her fleet exceeded the size of many countries' navies. She also expanded the scope of the business, branching out from simple attack-and-pillage jobs to protection schemes, blackmail, and extortion. Cheng I Sao's reach also extended to the mainland, where she set up an extensive spy network and developed economic ties with farmers who would supply her men with food.

If Cheng I Sao's business practices were exemplary, then her system of pirate law was nothing short of revolutionary. The code of conduct she wrote for her men prescribed much harsher punishments than previous pirate laws had. A disobeyed order was cause for beheading (as was stealing from the common plunder), and deserters stood to lose their ears.

Ironically, Cheng I Sao's most famous laws applied to the taking of female prisoners. Ugly women were returned to shore, free of charge. Attractive captives were auctioned off to the crew, unless a pirate personally purchased the captive, in which case they were considered married. Of course, if that pirate cheated on his new bride, Cheng I Sao had him killed.

The not-so-bitter end

Murder, thievery, and intricate crime syndicates will eventually garner the full attention of the law, and Cheng I Sao certainly had the authorities on her tail. But, here again, she proved more successful than her male counterparts.

Cheng I Sao repelled attack after attack by both the Chinese navy and the many Portuguese and British bounty hunters brought in to help capture her. Then, in 1810, the Chinese government tried a different tactic -- they offered her universal pirate amnesty in exchange for peace.

Cheng I Sao jumped at the opportunity and headed for the negotiating table. There, the pirate queen arranged what was, all told, a killer deal. Fewer than 400 of her men received any punishment, and a mere 126 were executed. The remaining pirates got to keep their booty and were offered military jobs.

As for Cheng I Sao, she retired with her loot and her new husband (former righthand man, Chang Pao) and opened a gambling house. She died peacefully in 1844, a 69-year-old grandmother. E-mail to a friend E-mail to a friend

For more mental_floss articles, visit mentalfloss.com

Entire contents of this article copyright, Mental Floss LLC. All rights reserved.

All About Pirates

  • E-mail
  • Save
  • Print
Home  |  Asia  |  Europe  |  U.S.  |  World  |  World Business  |  Technology  |  Entertainment  |  World Sport  |  Travel
Podcasts  |  Blogs  |  CNN Mobile  |  RSS Feeds  |  Email Alerts  |  CNN Radio  |  Site Map
© 2009 Cable News Network. A Time Warner Company. All Rights Reserved.