THE MOST SUCCESSFUL PIRATE WAS A PROSTITUTE

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.


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.