It’s Women’s History Month, and so this month I’m going to do some women-specified episodes showcasing some stories of awesome women during the 16th century. In this episode, we look at women pirates. Specifically, two main stories about women pirates.

Also, once you’re done, here’s another episode on A Day in the Life of Tudor Women you might find interesting!

Book Recommendations:

Pirate Women: The Princesses, Prostitutes, and Privateers Who Ruled the Seven Seas by Laura Sook Duncombe.

Pirate Women book

Transcript: Women Pirates

Hello and welcome to the Renaissance English History Podcast, a part of the Agora Podcast Network. I’m your host, Heather Teysko, and I’m a storyteller who makes history accessible because I believe it’s a pathway to understanding who we are, our place in the universe, and being more deeply in touch with our own humanity.

This is episode 163, and it’s a special one on women pirates. Because this week two very special events are coming together. First, it’s Women’s History Month and coming up to International Women’s Day. I’m a woman, so this is important to me.

Second, this week in 1496 John Cabot who was actually the Italian Giovanni Caboto, received letters patent from Henry VII to explore Newfoundland. Which was the nascent beginnings of the Age of Exploration in England which would reach its full culmination 100 years later under Elizabeth.

So I decided to mix the two and do an episode on Women Pirates. Also, this kind of fits the recent episode I did on sea shanties, too. So we’re seeing a pattern emerge. Which is basically that I have itchy feet and want to get on a boat somewhere. Anywhere. 

But first, a little admin. It’s been a long time since I’ve done a patron shoutout and I need to do a patron shout-out because my patrons are awesome. My patrons are the best patrons. So thank you to Bex, Taylor, Heather, Juliet, Shamala (love your name), Marie, Cheyenne, Sharon, Joelle, Nina, Kimberly, Joanna, Tracy, Alexandra, Justine, Rachel, Paul, Viviane, Jennifer, another Jennifer, (Jennifer M. and Jennifer H.)

Jill, Sharon, Michael, Bebet, Delia, John, Katie, Kimberly. Helen, Windy, Jim, Vicki, Donna, Cara, Sarah, another John, Susan, Celayne, Andrea, Katherine, Ian, Shar, Kendra (whose name is spelled wrong at Tudorcon 2019 name badge). Joanne, Kathy, another Katie. Rebecca from Tutors Dynasty, Al, Shandor, and Juergen (that’s my daddy). Thank you to my amazing patrons.

If you want to support this podcast, through Patreon and pledge your support, you can do that at patreon.com/englandcast.

Okay, women pirates. It wasn’t long after the very first sailors sailed into the waters that pirates followed, hoping for riches, and adventure. We might have a very specific idea when we think of pirates. My daughter is in love with all things related to Peter Pan, so we see a lot of pirate depictions, and there’s the eye patch, peg leg, and parrot. The pirates we see are pretty much always men.

For a long time, sailors would actually sign a contract prohibiting women from being on board. But women – creative geniuses that we are – would find creative ways around this, often dressing as men and sneaking on board. 

From the ancient Mediterranean period through the middle ages we see a handful of women leading ships. Sometimes pretending to be men, other times taking control on their own. Usually this would be when they were somehow related to another sea captain or pirate. Maybe it was a husband, and they took over after he died.

The Norse sagas tell stories of warrior princesses sailing to America, fighting sea battles. In the show notes – which will be at englandcast.com/womenpirates I will add a book list where you can dig deeper into women pirates if that strikes your fancy. But for the purposes of this podcast, we’re going to talk about three extraordinary women who sailed the high seas in the 16th century. 

Grace O’Malley

In Ireland, there is a museum to Grace O’Malley, the only museum in the world dedicated to a female mariner. Some of you who are Irish might catch me up on the fact that I’m saying Grace’s name in the Anglicized version, and not the traditional Irish, of how she would have known herself.

I say her name this way for two reasons – first, she doesn’t appear in the Irish records, so everything we know about her comes from England. Second, I can’t pronounce her name in the original Celtic, and I’m not even going to try. But I want to be clear that Grace O’Malley is a name given to her, and it’s not the name that she knew herself as. 

A few years ago I did an episode on the English relationship with Ireland, and I’ll link to that in the show notes. But for those of you who need a refresher, Ireland at this point was still ruled by smaller bands, and England was doing its best to bring it under English control in a centralized government. By the late 16th century, English nobles were building colonies in Ireland to try to take over it. 

One of the leading families was the O’Malleys, who were seafarers, and the legends say that her father was a prominent sailor by 1530 when she was born. Some stories say that she had a brother who didn’t want to sail, and so she took over her father’s business. Much of what we know about her is legend, but like so many legends there is likely a bit of truth underneath it somewhere, if only to show her character.

For example, one early story about her life says that when she was young there was a group of eagles terrorizing the animals on her land, and to save the livestock the young Grace ran into the eagles and attacked them, despite the fact that most of them were much bigger than she was. Apparently, this fight with the eagles left her with scars on her forehead that she had for the rest of her life. 

The head of the family was known simply by his surname as Ó Máille. Local folklore had it that when Grace was a young girl, she wanted to go on a trading expedition to Spain with her father. She was told that she couldn’t go because she was a girl, and that her long hair would catch in the ship’s ropes. So she cut off most of her hair to embarrass her father into taking her, or alternatively to sneak on board. She became known then as bald Grace.

Grace was educated, something that we know because later in her story when she met Queen Elizabeth, and spoke Latin with her. She married Donal O’Flaherty, heir to a powerful clan nearby. They had two sons and a daughter. While Donal was the head of the family, he spent much of his time off making war and fighting. So Grace was often left helping to take care of the inhabitants nearby.

Donal was killed in battle in 1565, and Grace vowed to take revenge on the clan that killed him. She herself took the castle that Donal had been fighting for. Then when it was clear that she wouldn’t inherit the chiefdom and would be expected to become a meek widow, she left and returned home to Clare Island with a group of her husband’s men who were still loyal to her.

Her leadership grew, and she wound up with a band of around 200 people, took her father’s ships, and launched her career on the seas. She sailed in galley ships with oars and a single sail, similar to a Viking longship. She knew the Irish coast like the back of her hand, and she would sail these highly maneuverable ships around preying on trading ships, taking what she wanted, and then escaping into the small islands and coves along the western Irish coast, where no one would be able to follow or find her. 

She married a second time, a man called Richard Burke. He had a fleet of trading ships, and a fortress called Rockfleet Castle. They had a good working relationship and one son. In 1576 an English representative visited their home, and Grace pledged her support on behalf of the family.

The fact that she did this on behalf of her husband, promising that he would do as she asked him to, led the English to say that she was “a notorious woman in all the coasts of Ireland.” Sir Henry Sidney knighted Richard before leaving home, and this made Grace Lady Burke

She supposedly gave birth to their son while she was sailing with Richard, and the day after he was born the ship was attacked by Algerian corsairs. Her men couldn’t fight them, and Grace was resting and recovering from childbirth below decks, but came up, cursing, “may you be seven times worse in one year, seeing you can’t manage for even one day without me,” and joined in the battle. The corsairs were so surprised by this woman, looking as if she’d just had a baby, coming up, that it supposedly turned the tide, and they won. 

She was first captured in 1577 by the Earl of Desmond while she was raiding on his land and was sent to Dublin Castle where she was kept in jail for 18 months. She was released in a bargain to stop her husband rebelling, but then she resumed her piracy, nearly 50 years old at this point. 

The English grew to hate Grace. She stood for everything the English wanted to subdue in Ireland, and she refused to become a submissive subject. Though the local chieftains respected her and did their best to keep her safe. But the English eventually kidnapped two of her sons, one of whom died in English custody.

So Grace took her case to a female Queen – Elizabeth herself. In 1593 she wrote to Elizabeth asking that her other son be released. She was honest about her past piracy, but she said that it was necessary in order to feed her family and people. She promised that of Elizabeth would grant them the right to hold their lands under English law, she would devote herself to sailing against Elizabeth’s enemies, and would answer to Elizabeth directly. 

Elizabeth found this all very intriguing, and loved the idea of this pirate queen writing to her. She sent questions to Grace for her to answer, and Grace wrote back her answers, offering up a picture of a smart woman, comparing herself to Queen Elizabeth herself. She set sail to England with the answers, hoping to meet Elizabeth in person.

This was an incredibly bold move, not just because she was a woman, but also because she was a well-known pirate, and England’s ports were filled with the bodies of hanged pirates and criminals. But she wanted her son back. By this point he had been charged with treason, and she knew that if she didn’t take decisive action, he would be killed. 

Grace and Elizabeth met in the autumn in 1593. We don’t have an exact recounting of the meeting, but there are plenty of legends about what they wore, who was taller, and apparently, when one of Elizabeth’s ladies offered Grace a lace handkerchief she blew her nose on it and threw it into the fire, much to the horror of said lady.

You can just imagine these two women meeting and having an amazing conversation. Both of them intelligent, bold, and taking on roles that were very different than what the world expected of their sex.

Grace was allowed to return home and her son was freed, and she resumed her piracy with Elizabeth’s blessings. In fact, the English were required to give Grace a pension, much to their outrage. 

Mary and Elizabeth Killigrew

The other story I want to tell you is about a mother-in-law and her daughter-in-law, Mary and Elizabeth Killigrew, part of a pirate operation running out of Cornwall. So one thing about Mary and Elizabeth is that there is a lot of uncertainty about whose role was what in this operation. Some historians actually combine them into one person, but it seems that the daughter-in-law, Mary, was responsible for many of the more daring parts of their story. 

Elizabeth Killigrew was the mother of Sir John Killigrew, a Vice-Admiral of Cornwall, and a blood relative to William Cecil. He was also a pirate. The family basically ran the piracy racket out of Cornwall. They didn’t always go out on the raids themselves, but they had the ships, they bribed the officials, and they handled payment disputes with crews. They properly assessed the stolen goods, giving the crown their share, and they were very successful pirates for the queen.

Elizabeth was walking a fine line at this point because she officially didn’t want to have pirates in her kingdom. But she made a lot of money from her “sea dogs”. That was what they were called. She kind of had to walk this middle line.

Mary Wolverston was the daughter of a gentleman pirate Philip Wolverston. She married Elizabeth’s son John after her first husband died. John had duties that necessitated travel. He was the Vice-Admiral of Cornwall and also the royal governor of one of the fortresses built by Henry VIII nearby. While he was away, Mary went out and did some pirating, preferring to be hands-on with the operation. 

They hid the stolen goods in their home, and paid officials to not see them. Working for them was a good gig, as their crews knew they’d be taken care of. Mary and Elizabeth would cook family meals for them in their main house sometimes. If a pirate was being followed by an official he would sail right to their home, and know that Sir John would row out and offer the official a lovely vacation hunting on their land for a few days in return for him looking the other way. 

Their racket lasted for decades, and they had pretty much all the Cornish officials in their pockets. But it was Mary who allegedly brought them down around 1582 when a Hanseatic ship sailed into the Falmouth harbor right to their home.

The weather was bad, and they were forced to anchor and send men ashore asking for shelter. The two men explained their situation to the lady of the house, Mary, who served them food and explained that the ship would be safe in the harbor, and they should ride out the storm as a guest in Penryn, which was nearby. The sailors, who knew that England and the Hanseatic League were at peace, agreed that this was a good offer. So they go off to this guesthouse. The boat is in harbor, everything seems like it’s good.

As soon as they left, Lady Mary looked at the ship and decided that she wanted it. She was almost 60 years old by now, but she still commanded a following. She gathered a crew including servants, and she sailed out to the ship that night, covering the oars with cloth so as not to be heard.

They climbed aboard the ship, killed any remaining crew they found, and took the treasures into the boats they had sailed out on. Supposedly some of the Killigrew pirates took control of the ship and sailed it to Ireland. When the gentlemen who had stayed in the guest house returned, and looked out at the harbor, their ship was gone and there was nothing there.

The two men lodged a complaint with the Commission for Piracy in Cornwall, which was run by Lady Mary’s son. The commission mysteriously was unable to find anything wrong, or discover who committed this act. But the captains pursued their claim, taking it higher and higher until it reached the desk of Elizabeth herself.

Elizabeth was stuck in a muddle. She couldn’t ignore the evidence that Mary was at fault her, and she didn’t want to make things difficult with the Hanseatic League. But she also didn’t want to lose the Killigrews because she was making a lot of money off of them.

Lady Mary and her servants went on trial for piracy and were all found guilty and sentenced to death. But Lady Mary was given a reprieve. Some say that it was her husband who secured the release, but others say that Elizabeth herself pardoned her. The Killigrews would stay on pirating for Elizabeth for the foreseeable future.

So that’s it for this week. The Book recommendation is Pirate Women: The Princesses, Prostitutes, and Privateers Who Ruled the Seven Seas by Laura Sook Duncombe. I’ll have a link to purchase in the show notes at englandcast.com/womenpirates.  

Let me know what you thought about this episode. You can get in touch with me through the listener support line at 801-6TEYSKO. Or join the new Tudor Learning Circle, which is a free social network just for Tudor history nerds. Thanks so much for listening, and I will be back in a couple of weeks.

[advertisement insert here: if you like this show, and you want to support me and my work, the best thing you can do (and it’s free!) is to leave us a rating on iTunes. It really helps others discover the podcast. Second best is to buy Tudor-themed gifts for all your loved ones at my shop, at TudorFair.com, like leggings with the Anne Boleyn portrait pattern on them, or boots with Elizabeth I portraits. Finally, you can also become a patron of this show for as little as $1/episode at Patreon.com/englandcast … And thank you!]

The Social media for Tudor Lovers

Join the Tudor Learning Circle. The only Social Network for Tudor nerds!