Guest Blogger Paula Fletchall-Bryner on Lady Pirates: "Cutlass Liz" Shirland

Scandalous Women is pleased to welcome Guest Blogger Paula Fletchall-Bryner to talk about Lady Pirates: “Cutlass Liz”

The story of Elizabeth Shirland (or Sherland), the lady pirate of Sir Francis Drake’s Spanish Main, is as far from black and white as you can get, historically speaking. In fact its one big pit of gray. The kind that makes researchers back away slowly without making eye contact for fear of losing a limb. That’s probably why so little has been written about “Cutlass Liz” and why what has been written tends to dismiss the possibility of her existence out of hand.

The legend goes something like this: Shirland was born in that most seafaring of English shires, Devon, some time between 1550 and 1560. In her early teens, for no reason specified other than she was one of those kind of girls, Shirland cast off her skirts in favor of breeches and chose a life at sea. Beginning in 1577, she served under Drake – arguably the most successful of Queen Elizabeth’s sea dogs – aboard his Golden Hinde. This voyage made Drake a national hero and his raids on Spanish shipping and towns along the coasts of Central and South America are the stuff of legend. Shirland got a taste of successful pirating, and she liked it. A lot.

The details of how Shirland went from seaman to Captain are vague but eventually she was at the helm of her own ship trying to mimic her hero Drake along the Main. She revealed her sex to her crew early on and started taking lovers from among them. If they displeased her in some way, she dispatched them with her trusty cutlass. Despite her success in prize taking, Shirland’s crew got fed up with her shenanigans and betrayed her to their Spanish enemies. Her ship was boarded in a night raid and Shirland was dragged, naked and screaming, from her cabin to be dispatched directly by the Spanish. This only after she killed her lover who was one of her betrayers.

Obviously there’s a lot of fantasy and wish fulfillment going on in the story as it stands. Though women at sea – either living openly as women or disguised as men or boys – were in no way as unusual as many modern writers would have us believe, women as sea Captains were a rare breed. Then there’s the moniker “Cutlass Liz” which some historians rank as downright impossible for any Elizabethan woman. When we add in the lusty nature of Shirland’s leadership and her dramatic death, it’s no wonder the story is generally dismissed. I would argue, though, that a closer look at the history surrounding the legend might yield more fact than fiction.

A quick search of a genealogy sight like turns up a myriad of Elizabeth Shirlands/Sherlands born between 1530 and 1600 in Devonshire. This immediately discounts the argument that our heroine must be any one of these women in particular. Elizabeth was an extremely common name at the time and Shirland/Sherland is by no means uncommon. The idea that no Elizabeth would be referred to as “Liz” during this era is a little far fetched as well. Nicknames for Elizabeth included Bess, Beth, Betsy, Eliza, Liza and Liz with the last being the most down at heel sobriquet. Famously – and notoriously – Grainne Ni Malley (known in England as Grace O’Malley) the fiery pirate queen of Ireland, called Queen Elizabeth I “Red Liz” referring not to the sovereign’s hair color (Grainne herself was copper haired) but to her propensity for killing her enemies.

The majority of England’s population did not necessarily benefit from what we imagine today as Elizabethan prosperity. As Joan Druett notes in her book She Captains: Heroines and Hellions at Sea, the decade of the 1560s was unusually difficult for the common folk of Britain. The climate suddenly became colder with longer winters and rainy, dismal summers. Crop failures were a regular occurrence and the seasonal fisheries along the coasts did not produce even half of their usual catches. Men and women turned to piracy as a last resort. Brigands in London were known to lie in wait for water taxis and other small boats and then wade out into the filthy water of the Thames to plunder whatever they could from those aboard. In such desperate times, more than one lone young woman who did not want to turn to prostitution envisioned dressing as a man and going to sea as a viable option.

Then too there was the general egalitarianism of what was to become the Royal Navy. The privateer fleets established by Henry VIII blossomed under his daughter’s patronage and a man (or woman dressed as one) who worked hard, had a head for heights and showed an aptitude could rise from serf to noble in the course of a career. The ultimate example of this came some 250 years later in Horatio Nelson. Born the son of a country parson, “Britannia’s God of War” as Byron named him died a Viscount and Vice Admiral because of his seafaring ability.

Finally, my argument for the viability of Elizabeth “Cutlass Liz” Shirland as a historical woman at sea if not a pirate captain hinges on the thing that makes the story seem ridiculous – her sex. We know now that many pirates and privateers in the Golden Age of piracy and beyond were of African descent. Most were escaped or freed slaves looking for work where they could find it and hoping for wealth like any other buccaneer. Some captained their own vessels. The vast majority of these men (and probably women) went to their graves in complete anonymity. Unlike Blackbeard, Bartholomew Roberts, Jean Laffite and numerous others, who were darlings of the press in their day, newspapers and broadsheets didn’t print stories about black sea rovers. In a time when blacks were considered less than human, the powers that were refused to even acknowledge the existence of black pirates much less their success. What then would make anyone think that the seafaring exploits of another chattel class – women – would be documented in detail? Anne Bonny and Mary Read not withstanding, most lady pirates are lost to history.

So, I leave it to you to decide. Elizabeth Shirland: Cutlass Liz the pirate or figment of an over-active imagination? I’m betting the truth can only be fished out of that gray area in between.


Cordingly, David Women Sailors and Sailors’ Women: An Untold Maritime History (New York; Random House, Inc. 2001)
Druett, Joan She Captains: Heroines and Hellions at Sea (New York; Touchstone, 2000)
Konstrom, Angus The History of Pirates (USA; The Lyons Press, 1999)

Paula Fletchall-Bryner holds a BA in Anthropology from Cal State University, Fullerton and a Certificate of Completion from the University of California, Irvine Writers' Extension. She spent ten years as an insurance executive and is now pursuing her passion - researching and writing about history. Her work has appeared in the periodicals No Quarter and The Lafitte Society Journal among others and she is currently putting the finishing touches on a historical novel about pirates and privateers in New Orleans early in the 19th century.

Here's the link to Paula's blog:


Anonymous said…
i've never heard of her but would dearly wish that she was a genuine historical character and not a work of fiction or legend.
she sounds like an amazing woman!
Pauline said…

I'm with you!


Thanks a bunch!
Timmy! said…
Ahoy, Pauline! Nice post and congrats on the guest spot. Thanks for intoducing me to another fun blog. You are indeed the Pirate Queen! While I find the salacious bits of this legend to be the most fun part of it, I certainly agree that the legend of Cutlass Liz seems plausible.
Hope Tarr said…
Excellent post, Elizabeth--and reading it ever so much more fun than working on Ye Olde Work-in-Progress. ;)

Years ago I subscribed to a piracy listserv. Fellow subscribers ran the gamut from oceanographers to former FBI agents to yes, re-enactors. The discussions were intriguing, the intellectual arguments among members especially so. In pt it was all so fascinating I finally had to un-subscribe simply to get any work done.

But I saved some of the better posts in a notebook binder, the ones on female pirates especially. And you're quite right. I don't recall Cutlass Liz coming up among O'Malley and the other Usual Suspects.

I'd like to think she was, if not all real, at least a little bit real, too.
Elizabeth Shirland, is my new hero and I'm ever so glad you introduced her to me.
Have a great week
Bearded Lady said…
I never heard of her either but some parts of the story must be true. Great blog too.
Thanks everyone, I'm glad that you enjoyed Paula's post.
Unknown said…
.Great looking urban art. I am so glad to get a peek at it!

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