Meet Rosie the Privateer! You can think of her as Rosie the Riveter – as a pirate. The inspiration for this watercolor painting came from listening to The Pirate History Podcast. The host, Matt, was talking about how the mostly-male pirates were very often busy sailing and looting, away from shore for long periods of time. This basically meant that the women who were left behind were in charge. They owned many of the local businesses, and were quite independent. He made a comment that they were quite like that icon of World War II in the United States, Rosie the Riveter, and suggested that if any artist were interested in drawing a pirate version of Rosie the Riveter, he would be quite interested to see it. So I thought… challenge accepted! I got to thinking through some of the basic details, like what her name would be, what sort of clothing she would wear, and what the slogan across the top of her poster would say, and wrote to Matt to see if he had any ideas. It turns out he did – lots of ’em.

The Slogan: We Can Loot It!
We threw some slogan ideas back and forth, and ultimately after saying bunches of iterations of the many options and running them by family and friends, I arrived at “We Can Loot It!” – you know, four mono-syllabic words, still pirate-y…perfect! (“We Commandeer It!” was a very, very distant second… “Yarrrrrs we can!” was a silly joke that I honestly still like *slightly* better, as it’s an answer to and affirmation of the original, but it doesn’t have the right number of words and stuff, and we didn’t want to get sued by the Obama campaign, etc etc.)

Her Name: Rosie the Privateer
Coming up with a name was really hard. Matt and I both were torn between wanting it to relate as closely as possible back to the original and wanting it to be historically accurate. So we were brainstorming other names that start with R, which names would’ve actually been super common for women living among pirates in the late 17th century (uh, Mary, or maybe Mary?), whether to call her a Buccaneer, or a Marauder, or what… somehow Privateer didn’t even make that original list! But even though it’s less obvious to non-pirate-historians than just going with “Pirate”(which, frankly, only doesn’t work because it’s one syllable short), it’s historically accurate *and* fits the need for it to be three syllables, *and* even has most of the same consonants and vowels in the mix as the original “Rosie the Riveter”.

Her Background
So, definitely Rosie the Privateer was going to be a badass. That was clear from the beginning. But how did she fall into this pirate lifestyle? Who were her parents? Did she ever actually sail?

It turns out that yes, of course she actually sailed, because she needed to have some excellent and period-accurate tattoos… So not only did she sail, but she was even a boatswain (or “bosun”) (see the crossed anchors between her thumb and forefinger?), had crossed over the equator and was thus a “shellback” (see her sea turtle?), and had been caught and tried once for her pirate ways (hence her branding with a P on her wrist, which she manages to obscure with her bracelets). She also had crossed the Atlantic (hence the anchor) and always kept home in mind (so she got that nautical star).

Who her parents were is another fun bit of her history. Her mom belonged to the Kuna tribe, and had quite a storied life herself. Rosie always wears her traditional Kuna jewelry – from her large bracelets made up of tons of tiny beads, to her mom’s ring, to her gold nose ring. The earring she picked up when she was on one of her first major trips to sea, when she realized that she’d do best to wear the standard “please take this payment and make sure I get buried” sailor jewelry. Actually, if you were to look at it closely, it’s got “Tortuga” engraved around the inside.

She actually doesn’t know who her dad was. Some pirate, for sure. People try to guess, saying oh he must have been one of those former English navy men who turned to piracy in between wars, or actually he was an escaped African slave who became the captain of this-or-that famed ship. But really – no one knows, not even her.

For some reason we can’t quite explain, just a marvel of the way things work out I guess, the button that she’s wearing happens to be the exact same skull and crossbones icon as is used on the Pirate History Podcast main banner. And she just happened to pin it where her soul sister Rosie the Riveter also wore hers nearly three hundred years later. Isn’t it funny how things work out??

Please note – I am not a historian, and you should do your own research on the history of women who were buccaneers, privateers, and pirates. Rosie the Privateer is obviously inspired strongly by history, but she is completely made up. You should not leave this article without a nice list of real-life female pirates to go research, though, so here that is:

Anne Bonny
Mary Read
Ching Shih
Rachel Wall
Jacquotte Delahaye – just kidding, she’s not real either!
Anne Dieu-le-Veut
Charlotte Berry
Ingela Gathenhielm
Lai Choi San
Charlotte Badger
Flora Burn
Sister Ping