Few historical figures ensnare the imagination in the same way as pirates do. The rum, the talking parrots, the hats and cloaks and treasure—all make for dramatic, theatrical tales. But what if I named Sayyida al-Hurra, Lady Mary Killigrew, Anne Bonny or Mary Reed? The first was the 16th century Morroccan pirate queen and the second was a "sea-dog" for Queen Elizabeth I. The third and fourth earned fame in the Caribbean in the 17th century. Through time these women's stories have become embellished so that it becomes virtually impossible to separate fact and fiction. Many of the stories came down out of oral traditions only later to be recorded.
In the Caribbean it became a free for all much of the appeal was in the opportunity to divest oneself of the societal roles and take part in what in essence was a multinational masquerade and make oneself anew.
While there have been no first hand accounts from these ladies we do have the second and third hand reportage. Were there successful female pirate commanders? I give to you the commander pirate Cheng I Sao, her fleet was larger than many of the legitimate fleets of the day. She married into a decent pirate operation but then expanded it beyond her late husband’s wildest dreams. Cheng I the most successful woman pirate of all time. Cheng I enforced a code of conduct that was unique in its harshness. Penalties for the offenses were above the norm for the era and the strict proscription of sexual activity, both consensual and nonconsensual, on- and off-board of the ship [Raping female captives was punishable by death and even if captives had consensual sex they would still be killed].
The way she surrendered only amplified her success. Her surrender was one for the books. She was able to secure pensions for her crew. She was so terrifying that she basically forced the Chinese government to pay her to stop pirating. It seems her calculation [with the surrender] was, the government is expecting somebody coming to them with a phalanx of burly bodyguards armed to teeth. And she comes in with a bunch of ladies. That would’ve at the very least been very surprising and shifted the balance to power, and forced everyone to reconsider. She was incredibly successful in her negotiations, so it was a smart gambit.
While quite probably many women pirates dressed in male attire others did not. There is the story of Grace O'Malley (Irish pirate of the 16th century giving birth to her youngest son aboard a pirate ship. The problem is we only have record of those who got caught.
The Vikings had their own Lady of the Seas; Ladgerda, the Viking pirate who said it was better to rule without her husband and murdered him after rescuing him. His fleet was in distress after he left her for another woman. She sailed in to save the day but had a knife in her skirt and stabs him and says, "ok I’m in charge now."
Anne Bonny and Mary Read are just two of the famous female pirates who pillaged their way to fame. (Lebrecht Music and Arts Photo Library/Alamy)
Information found on Smithsonian.com and in the book by Laura Sook Duncombe "her new book Pirate Women: The Princesses, Prostitutes, and Privateers Who Ruled the Seven Seas.