Who Was The Most Successful Pirate in History*

Any guesses?  Edward Teach, commonly known as Blackbeard?  Captain Kidd?  Captain Morgan?** Grace O Malley, aka the Pirate Queen?    Sir Francis Drake?***

None of them are even close, though Drake has the distinction of capturing what may well have been the largest prize taken in a single raid: the Spanish galleon Cagafuego.  The title goes to Cheng I Sao (aka Hsi Kai Ching, Ching Shih, Lady Ching,  or Mrs. Ching depending on the vintage and quality of the account you read.), who terrorized the South China Seas in the first half of the nineteenth century–a time when many Chinese women were literally hobbled by bound feet.****

Cheng I Sao

Piracy was a family business in nineteenth century China.  Pirate clans lived on their boats–some of them lived their entire lives without setting foot on land.  Within the world of the pirates. some women held rank, commanded ships, and fought shoulder to shoulder with their male counterparts.  Cheng I Sao took female participation in the family business to a new level.

According to popular accounts,  Cheng I Sao was a Canton prostitute who married the successful pirate Cheng I in 1801 and soon became his partner in building a successful confederation of pirates from competing clans. When Cheng I died in 1807, his widow took over. She avoided succession struggles by appointing her adopted stepson as her second in command and later marrying him.

At the height of her success, Cheng I Sao controlled 1500 ships and more than 70,000 men, organized in six fleets, each with its own flag and commander. (Talk about a pirate queen!) Her fleets attacked ships of all kinds, from small traders to imperial war ships, and ran a protection racket along the coast.

By 1809, Cheng I Sao was powerful enough to threaten the port city Canton (now Guangzhou).  The Chinese government turned to the European powers for help, leasing the 20-gun ship HMS Mercury and six Portuguese men-of-war.  Big guns were not enough to defeat the pirate admiral’s fleet.  In 1810, the Chinese changed tactics and offered the pirates amnesty.

Cheng I Sao decided it was in her best interests to negotiate peace terms with the Chinese empire.  She proved to be as effective at the bargaining table as she was on the deck of a ship: the Chines granted her pirates universal amnesty, the right to keep the wealth they had accumulate, and jobs in China’s military bureaucracy.  Cheng I Sao retired in Canton, where she reportedly lived a peaceful life until her death at 69 “so far as was consistent with the keeping of an infamous gambling house.” *****

*  If I had my act together I’d have written this post in time for Talk Like A Pirate Day, which was last Friday.  All I can say to that is —-aaargh!

** Not just a brand of  rum

***After all, a privateer is just a pirate with a license to steal

****They were also barred from holding public office and had limited opportunities for education and employment, but this didn’t make China unique.

*****What?  You expected her to take up knitting and mahjong?


  1. Bart on September 24, 2014 at 12:51 am

    This post is another example of why I love your website. Historic footnotes like this is what keeps my heart pumping.

    • pamela on September 24, 2014 at 1:20 am

      Many thanks. 🙂

  2. Davide on September 24, 2014 at 6:46 pm

    Well family enterprises are always solid…

    As for the most succesful pirate, I’d like to nominate Khayr al-Din also known as Redbeard. He went from humbly origins to be Bey of Algiers and an ottoman admiral.
    Piracy in the mediterrean is an argument sadly neglected by mainstream history, yet one of the most interesting.

    • pamela on September 24, 2014 at 7:44 pm

      Redbeard is a definite contender. Thanks for the reminder.

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