Lady Pirates: Arguably the Most Successful Pirate Ever

Cheng I Sao's name seems like it would make today's tenacious heroine fall by the wayside of history's long road. It means simply "Wife of Cheng". Her own given name is lost to us entirely. Fortunately, though, her amazing exploits are not.

Cheng I Sao was born in China, probably around 1775. There seems to be no real documentation of her family's standing or station but they probably weren't living high on the hog. At some point in the late 18th century, Cheng went to work in a brothel.

These kind of establishments attract some colorful characters and it was here that Cheng met her future husband, Cheng I. By the time he hooked up with Cheng, Cheng I was a powerful pirate king, in charge of a loose confederation of hundreds of junks and thousands of men that raided local and foreign shipping out of a base in Macao.

Upon their marriage, Cheng I brought his new wife into the business and she seems to have gone at it with gusto. She was not from a piratical family as far as can be told but, by the time her husband died somewhere off the coast of Vietnam in 1807, she had the pirating thing down. Cheng stepped up to take her husband's place and work the Pirate Queen angle for all it was worth.

No fool Cheng, she knew that many of the 50,000 or so pirates that now reported to her would never agree to a woman as their leader. Using the same shrewdness that would see her through to a ripe old age, Cheng called up her husband's adopted son to become the ostensible leader of her Red and Black Flag Fleets.

The young man, who was around twenty years old at the time, was named Chang Pao. He was a fisherman's son who had been captured by Cheng I and looked on fondly by the pirate king. So fondly, in fact, that gossips said there was a sexual relationship between the teenage Chang and Cheng I. Whether or not that was true, it is known that Mrs. Cheng and Chang became lovers not long after Cheng I's death and eventually the two were married.

With her power over the pirate confederation now secure thanks to her relationship with Chang, Cheng set about strengthening her operation through written laws. The standards of pirate codes were there: distribution of booty, respect for superiors, etc. but Cheng added some interesting points that are worth a mention. Several capital offenses were noted, with beheading being the standard form of execution. These included failure to report for duty, refusing to act on a direct order and raping female captives. Interestingly, if it was determined that the female captive had consented to sex, the pirate would be beheaded anyway. And the female captive would be tossed overboard with a weight around her legs. Also written in the code was the pirates' right to leave homely female prisoners on shore and keep only the pretty ones. I'm getting a mixed message here, Mrs. Cheng.

Under the impressive leadership skill of Cheng, the confederation thrived. Protection money became the order of the day and certain industries routinely paid Cheng and her boys not to raid their ships. By 1809, the salt trade was virtually in the Pirate Queen's hands as her ships escorted salt junks where ever they went. Even the Chinese military tried to avoid Cheng and her pirates with stories of Army Generals sabotaging the ships they were supposed to sail on to stay out of Cheng's way.

Eventually the Government of China got fed up and, in 1810, Cheng agreed to sit down with officials and make a deal. It was agreed that no moneys would be repaid by the pirates and that none of them would be prosecuted in court. Many of Cheng's Captains were welcomed into Navy service. Her own husband was given a cushy government job that set the couple up for life. Add negotiation to her long list of accomplishments.

Mrs. Cheng took her fortune and invested in a brothel and gambling house which she ran until her death around 1840. She may very well have been the most successful pirate that ever lived, especially considering the complete lack of reprisal by China's officials. Even the Pirates of the Caribbean movies gave her a nod in the formidable character of Mistress Cheng. I wonder what Cheng I Sao would think about that.