Dark History - 162: Secrets of the Bloodthirsty Women Who Ruled the Sea

Episode Date: March 12, 2025

Hi friends, happy Wednesday! All great rulers at some point had to deal with the people who had the real power… pirates. I know. It sounds like a joke. But it’s true.  For centuries, pirates were a huge power to be reckoned with. They didn’t follow any rules, they were violent, unpredictable, and there were tens of thousands of them just waiting to pounce on other ships or cities at any given moment.  Surprisingly, I discovered that some of the world’s most famous pirates were *women*. And their backstories… you guys. I was shooketh. So much drama. I had to spill the tea. Welcome to the Dark History of Pirates. I appreciate you for coming by, and tune in next week for more Dark History. I sometimes talk about my Good Reads in the show. So here's the link if you want to check it out. IDK. lol: https://www.goodreads.com/user/show/139701263-bailey FOLLOW ME AROUND Tik Tok: https://bit.ly/3e3jL9v Instagram: http://bit.ly/2nbO4PR Facebook: http://bit.ly/2mdZtK6 Twitter: http://bit.ly/2yT4BLV Pinterest: http://bit.ly/2mVpXnY Youtube: http://bit.ly/1HGw3Og Snapchat: https://bit.ly/3cC0V9d Discord: https://discord.gg/BaileySarian* RECOMMEND A STORY HERE: [e-mail] Business Related Emails: [e-mail] Business Related Mail: Bailey Sarian 4400 W. Riverside Dr., Ste 110-300 Burbank, CA 91505  ________ Credits: This podcast is Executive Produced by: Bailey Sarian & Kevin Grosch and Joey Scavuzzo from Made In Network Head Writer: Allyson Philobos Writer: Katie Burris Additional Writing: Alexander Elmore Research provided by: Dr. Elizabeth Bejarano Special thank you to our Historical Consultant: Laura Sook Duncombe, author of "Pirate Women" and "A Pirate's Life for She"  Director: Brian Jaggers Edited by: Julien Perez Additional Editing: Maria Norris Post Supervisor: Kelly Hardin  Production Management: Ross Woodruff Hair: Angel Gonzalez Makeup: Roni Herrera ________ Right now, listeners of this show can get an extended 30-day free trial! Just go to https://www.dipseastories.com/darkhistory to start your free trial.  Stop putting off those doctors appointments and go to https://www.zocdoc.com/darkhistory to find and instantly book a top-rated doctor today. Start listening today when you sign up for a free 30-day trial at https://www.audible.com/darkhistory As a special offer for listeners, new customers GET 15% ALL Lume products with our exclusive code - and if you combine the 15% off with the already discounted starter pack, that equals over 40% off their Starter Pack! Use code DARKHISTORY for 15% off your first purchase at https://www.lumedeodorant.com. 

When we think of the world's most influential rulers, we think of about like kings, queens, emperors, dictators, right? History has taught us that's where all the power was, but that's just not true. In fact, all great rulers at some point had to deal with the people who had the real power. Pirates! For centuries, pirates were a huge power to be reckoned with. They didn't follow any rules, they were violent, unpredictable, and there were tens of thousands of them just waiting to pounce on other ships or cities at any given moment. So naturally, I had to look it up. Oh, most famous pirates, you know,

thinking that it was just gonna be like pictures of, ah, who's that guy from SpongeBob? He has the wooden leg, pig leg thing. Anyways, I was thinking it was gonna be like that, you know? Instead, guess what I found out? I discovered that some of the world's most famous pirates were women. Oh, what a thought.

And their backstories? Ah, shooketh. So much drama. I had to tell you because this is an interesting one. Welcome to the dark history of pirates Who are ladies? Hi friends, I hope you're having a wonderful day today. My name is Bailey Sarian and I'd like to welcome you to my podcast, Dark History. Here we believe history does not have to be boring. It might be tragic,

sometimes it's happy, but either way it's our dark history. Before we get into it, don't forget to like and subscribe because I'm always here for you posting new content. And let me know what you think because you know I love hearing from you in the comment section. Now let's get into today's story huh? Okay before the pirate community comes for me, I know there are tons of pirates I could have included in this episode, but I just picked two. Two that I really loved. And they happened to be women. I never heard of women pirates.

I didn't even know that, like, it was a thing, right? So when I saw this, I was like, oh, incredible. When you think about it, tons of men, men pirates. But there were plenty of women who were pirates as well. They're just forgotten by history, you know? Now, what is a pirate? A pirate is defined as a person who attacks and robs ships at sea.

I personally couldn't believe how much power this first pirate had. She's considered by many as the most successful pirate in history. And she was in power during the late 1700s in China. Listen, being a woman back then, it was extremely difficult to get any sort of power or respect on land or sea. So this woman was Cheng Yi-Sao and she was born in 1775. Not much is known about her early life, but what we do know is that she was born in 1775. Not much is known about her early life,

but what we do know is that she was born to like the everyday person, not people with power who historians seem to like to write about. What we do know is that she was born in China during a truly chaotic time. Between 1750 and 1800, the population of China increased from 181 million people

to 297 million people. Essentially, like an entire new country got added to society. Now this matters because the city was completely packed to the brim. It was like people were just spilling out, like where do they stay, you know? So people actually found ways to live on boats in the water because there just wasn't enough space for them on land. So an entire group of people started living on the water and they were called the Tonka. Tonka? The Chimp? Tonka! Tonka the Chimp! I know I didn't think Tonka the Chimp was gonna be here. And Cheng Yi-Sao was

actually one of them. She grew up literally on water. She knew her way around a boat pretty dang well. She knew the water, she knew how it worked, she knew what it was like. You know, living in such a big crowded city gave her a lot of street smarts. And according to records, her first job was as a sex worker. And this wasn't just to make money.

She knew the only way that she could move up in society was to gain a little bit of power. And the way that she did this was by learning secrets about the local businessmen that she had sex with. Some say she would strategically trade these secrets so people knew she was the person to go to for important information. And sometimes I think like if I weren't doing

what I'm doing now, I think I would be a sex worker, but then I would try and make it to the top and try and get secrets on everyone so I could blackmail them. That's what I would do. Or go to college. Being a woman, we can do those types of things. Okay, anyways, this created a position of power for her and she

really like shows her true colors during this time. She used the influence she had to protect other sex workers around her since you know it was a very dangerous job. She could have been selfish and blackmailed people, Bailey, but instead she made sure that the men knew not to mess with her or the sex workers around her or else she'd spill their secrets. Do you want that Brad? Do you want everyone to know what you do alone in your room, Brad? Do they know that you're fucking your cats Brad? Around the year 1800 she is now in her twenties and her life completely changes. She meets a man. Oh, a man. A man named Chang-Yi.

What a juicy episode today, huh? I know. It seems like things were just a little bit more exciting back then, especially if you were a pirate. Mm-hmm. Ever since Joan heard that we were doing this episode, she's been obsessed. She hasn't taken her little pirate costume off all week.

No bad bird. I will not watch Pirates of the Caribbean with you for the 500th time Joan. Ask Paul. Listen I know you've been a little desperate for some romantasy Joan. Let's be honest we all are huh? Well that's why I'm so happy we found Dipsy. Dipsy is the female founded app for spicy audiobooks and more. Created by women for the female gaze. Their app has over 1,000 spicy audiobooks all crafted by a team of professional writers and top-tier narrators. So if you're loving this week's episode of Dark History, honestly you're gonna love Dipsy. Because whether you're looking for like a rugged cowboy or a Scottish sailor or maybe I don't know the god of the underworld, you'll find characters

that you'll just love. With their easy to explore app you can search for your favorite romance genres like contemporary, historical, western, yee-haw, and more. Is there a pirate section? There are new chapters released every week so you'll always find something new to enjoy. So relax a little bit, put on the headphones, sit back, take off your pants, and enjoy. Right now, listeners of this show can get an extended 30 day free trial.

Just go to dipsystories.com slash dark history to start your free trial. Just go to dipsystories.com slash dark history to start your free trial. That's dipsy d i p s e a stories dot com slash dark history for 30 days of full access for free. Visit dipsystories.com slash dark history. So Cheng Yi-Sao has managed to make a name for herself through sex work. She learns to trade secrets and she also creates a powerful community of allies by protecting her fellow sex workers. Then around 1800, Cheng Yi-Sao's life completely changes when she meets a man named Cheng Yi. I know, I was like, what are the odds?

They have the same name, but this is actually where she gets her name. We don't know what her birth name was before she married. Back then it was like, when you marry someone, you just took your man's name and like, that was it, that's your name now. You have no name, your name is your man's name. So she goes down in history as Cheng Yi Cao.

So that's what we're calling her. Sorry, girl. So at some point she meets this man right Chang Yi and she's getting to know him. She's like hey so what do your parents do? Like what do your parents do? And he's like um we have a family business. And she's like oh my god that's crazy. What's the business like farming or something? And he goes no we're pirates. He goes, no, we're pirates. Huh, pirates? Yes, Cheng Yi came from a family of pirates

and they'd been pirates for over 100 years. It was in his blood. Now, to normal girls, this might scare them off, but Cheng Yi Cao, she's not like normal girls. She was like, what? Hot, I'm in, and the two get married. So he and his family were actually just part-time pirates in the spring and the summer.

In the fall and winter, these pirates were actually fishermen. In China, fishermen were not living the best lives. In the spring and summer, there were terrible monsoons, which made it almost impossible to earn a living by fishing. So the workers had to find other sources of income. So they turned into pirates. Professor Diane Murray describes the life

of a fisherman at this time as quote, "'So miserable that for many, a successful pirate foray was the sole hope for a better life.'" Now this marriage wasn't exactly about love you know? There were some love between Cheng Yi and Cheng Yi Cao but the real reason they got married was for business and opportunity as many people did you know back then. Cheng Yi Cao knew being a pirate's wife would bring in lots of money and also

power. Things she'd been working toward her whole life. So she made a point to not only be a supportive wife but one that her pirate husband depended on. She would help her husband strategize on what places to take over, what ships to attack, who to kidnap, and how to defend themselves. That's kind of cute honestly honestly. Like, honey, what do you think? I think we should like invade this place. I think we should like rob this place. They're bonding. She would often negotiate deals on behalf of her husband because she was much better at dealing with people than like he was. And as it turns out, the two of them were an unstoppable force at sea. So things are going great

for the couple. Cheng Yi-Sao has even given a son. Her husband, yeah given a son, listen to this, her husband kidnaps and enslaves a 15 year old boy. His name was Bao. So pirate kidnappings were so common back then, the government had to invent laws around what was happening. If you were kidnapped by pirates, you were either killed, held for ransom, or you were forced to join the crew as a pirate. So when 15-year-old Bao joins the crew,

Cheng Yi-Sao takes him under her wing. She even makes him like her little protege. I mean, Bao didn't have much choice. He was kidnapped and forced to be there. So he's like, this is my life now, great. Legend has it Bao is initiated into the crew through something called homosexual liaison. We don't know exactly what that entailed.

This was interpreted by historians to mean that they probably forced Bao to have sex with the pirates on the boat. Now Bao follows around his adopted father and mother doing whatever they order him to do. He even helps when it comes to looting towns and ships and stealing their gold. It sounds so fake right? I know I always think that too. Like I can't believe this was real. So uh the parents they're impressed with how Bao was doing. They're like this kid's good. I'm glad we abducted him and enslaved him and then had him raped. Good job you guys. But they decided to make him the captain of his own ship and this is perfect timing because it was 1802 if you didn't know and Chiang Yai was called away on a family affair. Now according to legend, someone

in his family dies and leaves him a huge fleet of ships with thousands of crew members. Around the same time, there's a major change in the pirate world. For the first time, multiple pirate crews and ships are banding together. This is because nearby in Vietnam, a new law that would prosecute pirates goes into effect. So after inheriting his family's pirate ships, on the way back home,

Ching Ye also like picks up these pirates that were trying to escape this new law. He's coming back with like quadruple the army that he had before. And it's like, okay, great. So most wives would be like, honey, you didn't tell me you were bringing so many people over, I would have cleaned up a bit.

But Changying Cao, she was like, oh, fuck yeah. Now we're stacked with power. There's so many people and ships to manage. She's now the one calling the shots. She's like, yes, yes. And she becomes the mastermind behind her husband's pirate conquests. I need a new dentist.

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Stop putting off those doctor's appointments and go to zocdoc.com slash dark history to find and instantly book a top rated doctor today. That's ZocDoc, Z-O-C-D-O-C dot com slash dark history. ZocDoc.com slash dark history. Zocdoc.com slash dark history. So Cheng Yi returns from his journey with a giant pirate crew. And since he's always out on the ocean

fighting other pirates, Cheng Yi Cao becomes the mastermind behind the whole like operation. So within two years, she has control of over 70,000 pirates and 400 ships. Damn, I know. So naturally, word began to spread that Cheng Yi-Sao was running this huge operation and she's a shit. Okay.

And her ships start getting attacked left and right by rival pirates. They're pissed. Who's this woman? In response, Cheng Yi-Sao decides to create something kind of unheard of within the pirate community. A rule book. And this wasn't just to be annoying, you know? She knew the pirates had to stick together in order to win their battles or else their army was going to fall apart. So she creates this rule book. This is why you need a woman, because we're organized, okay? And you need rules in place to thrive.

So for example, she had a rule to like, never take treasure that's not yours. It was essentially finders keepers when it comes to stolen treasure, but Chang Yi-Sow said it was against the code to steal your friend's booty. Interesting how it applies to certain things, but not other, like rape is okay,

but don't steal their money when you do it. So if you're stealing your friend's treasure, it's gonna create distrust on the ship and people are gonna turn against each other. And in this new rule book, if you did get caught stealing from your fellow pirate, you were going to be sentenced to death by decapitation. Her rules end up being really successful.

And by 1805, it's signed by all of the members of their crew. And people genuinely like being under Chang Yi-Sao's rule. She gave the orders at the top and her husband was essentially boots on the ground, manning the men on the ships. But just as things are going well for the two, things take a bad turn. In 1807, Chang Yi dies. Now we don't know how he dies, but there are some records that show he may have fallen

off his ship during a bad storm and drowned. Other people think he was killed by rivals and I mean that would make sense. Either way the death was unexpected and many people outside the pirate community expected Chen Yi's pirate empire to fall or fail after he died but it didn't because guess who's in charge bitch? Chen Yi Cao. She's like that's Oh yeah. In fact, as soon as her husband died, Cheng Yi-Sao was like, I'm not going anywhere bitch. You know, she wasn't about to be the crying widow who spent the rest of her life crying. You know? She immediately beelines for her husband's closest advisors and essentially tells them, hi. so I'm going to take over the world and

let's just say it would be a good idea for you to support that. They agree because listen if they don't agree she's gonna decapitate them, you know? I mean they've seen this woman at work for almost a decade they're not about to mess with her. She needs to essentially get all of the crew on the ships to back her, right? So she gets, she's like, goes to them, like, haven't I made your life better? Why would you leave?

I'm amazing, I've done great things, right? And essentially like the crews all agree, the pirates, and they're like, yes, ma'am, you can stay. So everyone is on her side. She's got the advisors, she's got the pirates and they're like yes ma'am you can stay. So everyone is on her side. She's got the advisors, she's got the pirates, but she's still missing one extremely important key to keeping her power. A husband. Ugh I know even though she was in charge of all these men, it was still a different time and they wouldn't trust a woman without like a husband back then. So the pressure's on, she needs to find a husband.

And honestly, when you think about it, she's got a lot of big crew. So she's got variety, but she's looking around. She's like, if I squint, you're kind of cute. Goes the other one. No teeth, peg leg. Okay, what about that guy over here? Oh no. You know, it's just the options were limited. So she gets to thinking, um, like what do I, I need a husband and uh, to look it around. Her eyes land on Bao, 21 years old at this point.

Remember Bao, the son that they stole? Yeah, he had been working along her and her husband the entire time and he had proven himself to be an incredible captain, pirate, and lover. That's right, Bao and his mother were allegedly having a hot and heavy affair the whole time her husband was off traveling and dealing with other pirates.

Now to her, Bao was the obvious choice because he was loyal. She knew he could handle day-to-day operations. She would be the brains, right? And he would be the brawn, the brawny man. And no one amongst the crew objects to this. I mean they're probably like, okay weird but cool. When Chang Yi-Sow officially takes over with her new husband slash son, she makes a few changes to the pirate rules. Mainly she focused on women and villagers. For example, if you were a villager who helped the pirates during a raid,

you couldn't be harmed or stolen from. If a pirate did harm a helpful villager, they'd be beheaded. Also, the pirates weren't allowed to rape or abuse the woman they encountered during their raids. Which is nice. If they wanted to have sex with a woman, they had to get married. Alright? So they were like, they found a woman, they had to get married. So they found a loophole and they were like, well just fuck each other. If anyone was having sexual relations, it had to be reported to Cheng Yi-Sao or else you would lose your head. Cheng Yi-Sao always found a way to control everything from behind the scenes.

One of the ways she maintained control was through religion. So the pirates, surprisingly, were very religious. They believed in some type of Chinese folk religion and they used to pray to the gods before doing anything. Most of the pirates were so religious that a temple would be built on one of their largest pirate ships. So she would send Bao down to the ship temple and tell the priestesses whatever her plans

were. So when the pirates would show up to the temple and pray for guidance, the priestesses would tell them to do whatever Cheng Yi-Sao said. During her reign, the pirate world is living in its glory days. An official historian of the Pirate Federation wrote, Peace and quietness was not known by the inhabitants of the sea coast for a period of 10 years. I wonder what the fish and whales thought and stuff. They were like, whoa, shit's crazy up there.

Anyone? No? Okay. Chang Yi-Sao was known to be relentless. She never let these pirates rest. They killed over 12,000 people during their raids over the years, but it wasn't enough. If there was an opportunity to steal someone's riches or take over, she ordered her pirates to do so.

Despite that, these pirates were never scared of anyone's ships coming their way. They always knew under Cheng Yi Cao's rule, they had nothing to worry about. They were the ones who were the threat. But finally, the party had to come to an, oh, you know what's funny? This is a complete side note, but this reminded me of, do you guys have that app next door? It's like where people in your neighborhood

can post like what's going on in the neighborhood. So a lot of the times they'll post like, hey, suspicious person outside, whatever. So funny story, I went on a walk. I went on a walk and I'm tattooed. I don't know if you know this, tattooed and I had my hat on. And I was on my walk and I saw this car, obviously a hoarder's car, okay? It was filled to the brim with stuff. So I took a moment, I was like looking in the car,

I was looking around, and I was looking in the car, just like, damn. Anyways, so I mind my business, whatever. The next day, I go on the neighborhood app, and there's like a screen grab of me from someone's camera. I was the suspicious person outside looking in people's vehicles. And in that moment, I was like, if I'm the threat,

then that means I am safe. You know? Like, I felt oddly safe. Like people are afraid of me. That's kind of like, that's great. I'm the threat was my takeaway from that. And then I left a comment like, listen here, you bitch. Maybe if you cleaned out your car,

I wouldn't be stopping and looking. I'm actually your neighbor. I'm looking at you right now. You're on the toilet because I can see directly into your window because you refuse to get curtains. Getting back to the story, the party, you know, great. They're on top of the world. It has to come to an end, as all stories do. And Cheng Yi-Sou was just, she was too powerful.

All these pirate captains became obsessed with getting rid of her, killing her, and taking over her army. In 1809, she was on a ship that was being targeted by the Chinese Navy and Portuguese ships. They teamed up to take her down on the open sea. They fired at her ship for weeks. They tried setting it on fire and a lot of people on the ship ended up dying but they never caught her. She finally managed to sail away unharmed after three months of constant battle. Now even though this victory was like a flex you know she's like yeah it was also a sign to her that this violence would never come to an end. The government was focused

on killing her and would team up with anyone to do so and we don't know exactly how old she was but you know at this time like she wasn't a young woman anymore, and the pirate life was no longer for her. Maybe she's ready to settle down or something. So she began to bargain with the Chinese government. When she walked into the meeting room, people were freaking out. They're like, oh my God, is that that pirate bitch? I heard about that bitch.

I'm so sad. So she came in and she's like, look, I have no plans to apologize. And also I'm not gonna face any consequences for my actions. Thank you so much. Essentially, she's like, you're gonna listen to me or like me and my pirates

are gonna go back to ruining your life, Brad. Remember? Cause I remember. Pepperjibba remembers. So after a long negotiation, the government agreed that she and any of the pirates who worked for her could walk away without any charges. Cheng Yi-Sao made sure that she and Bao got the protection they needed. She made the government agree that Bao could continue to lead a group of about 80 ships

working in the salt trade industry. As for herself, she got out at the right time. She served no jail time because she retired rather than being captured and after decades at sea she was a very rich woman. Later in life, rumor has it, she used that money to open up a little tea room. That's cute! She had her retirement business going on just living her life. 20 years later in 1844 at the age of 69, Chang Yi-Sow died.

Though on paper it said she was the wife of an army general. She was so much more than that. Yeah, she was a wife but she also died as the most successful pirate of all time. And that deserves a snap, am I right? Are you wearing a cowboy hat? Okay, good for you. Honestly though, I'm waiting for that movie. Where's that movie? A badass woman pirate? Come on. We can leave out the part about her fucking her son but you know, pretty cool. Well, not all pirates get a happy ending. Because of that, a lot of these stories get lost to history. But this next story is all about a pirate who made a name for herself, not because of her riches, but because of how much of a badass she was.

I can't believe that no one has made a movie about her life because it's wild. Paul has been pressuring me to try yoga. He's really getting into the, you know, the yogi lifestyle I think they say. Paul, do you want to show them one of your poses? If you're on a health or wellness kick like Paul, well you should check out Audible. Yeah, Audible, what? Well, with Audible you can explore over 1 million audiobooks, podcasts, and exclusive Audible originals that'll inspire and motivate you.

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Start listening today when you sign up for a free 30 day trial at audible.com slash dark history. So have you heard of Anne Bonny? No? Okay, well this is the next pirate we're talking about, a woman. Anne, she was born in Ireland in the late 1700s. Sorry about that.

We don't have a birthday because Anne's birth was kind of scandalous. She was a child of an affair and you know how that goes, especially in the 1700s. You don't mention that, okay. Anne's father, William, had an affair with his housekeeper while his wife was traveling. Word started spreading around town and William tried his best to cover up the scandal. And when Anne was born, he dressed up Anne as a boy and claimed that he had a son with his wife, not the housekeeper.

William even started calling her Andy. This went on through like a good chunk of Anne's childhood, but what we do know is that people were not, they did not buy William's story. William ended up moving away from the British colonies to North America, so he, Anne, and her mother could start a brand new life away from scandal.

But their life in America wasn't much better. William struggled to find a job and make a good living, and Anne, she struggled with her identity. In America, she wasn't Andy anymore. Now she was Anne. Very confusing. She'd spent her whole childhood acting and being treated like a boy.

She was the opposite of a dainty lady in society and she was known for like temper, outbursts, and violence, stuff like that. Anne did find her place with a very particular group of people in town, the pirates. Now it's unclear where she met the pirates, but we do know she loved that they were bad boys. William was so upset his daughter was associating

with these types of people, but William's disappointment didn't stop Anne. She actually ends up marrying a pirate named James Bonnie. That's where her signature last name comes from. William, her dad, was livid. He actually ended up disowning Anne because of this. Anne, he kicked her out of his house. Rumor has it, Anne was pissed. She knocked over a candlestick and set fire to her father's house and his land. Her new husband James wasn't like a superstar when it came to the world of pirates. He was actually kind of just basic pirate.

He not very high up. You know, she loved him and she even joined him on pirate journeys on his ship. Eventually Anne and James end up in the Bahamas. They traveled there because the Bahamas was considered a safe haven for pirates. But apparently there was a new governor in town and he wasn't so happy with his town being a vacation destination for pirates. You know? So the governor starts offering money to any pirate who became an informant for pirates. So the governor starts offering money to any pirate who became an informant for him. And he wanted to do this so he could nail down

the pirates in town. And so James takes the bait. Oh yes, Anne's husband becomes a snitch. This totally goes against pirate code, babe. Anne took the pirate life very seriously and was not happy with her scum of the earth husband doing this to her fellow pirate communities, okay? So Anne's in the Bahamas.

She's not happy with her life. She's not happy with her husband. Her dad sucks. She's in a bad place. She's in a dark place right now. And then out of nowhere, a man named Calico Jack walks onto the island. Jack is the head bitch in charge of all the pirates, okay? And when he shows up to town, immediately there's like a vibe shift.

Unlike her lame husband, Jack commands respect from everyone he meets and he even takes Anne's breath away. Take my breath away. When Anne saw Jack, she's like, yes, that's what I want. That man. And you know, when a girl has her eye on the prize, she's gonna get that prize. You know?

He was the most handsome, suave man Ann had ever seen. She probably saw his dick outline too. Just kidding. So she's a little flirty with him. She's like, Jack, that's so crazy. You like do stuff like the boat and stuff, Jack. That's crazy. Pirate stuff?

Yeah. Oh my God. and stuff Jack that's crazy. Pirate stuff? Yeah oh my god. So yeah that's crazy. So they're flirting with each other and then they end up falling madly in love. Jack is like babe I love you let's get married and Anne's like I'll never let go Jack. I'll never let go. And she doesn't. So remember she is still technically married. Well Jack and Anne are now in love, and she's like, look, I'm still technically married. And Jack's like, don't worry, baby, I'll handle it. So Jack goes up to James and he's like, look, I'll pay you to divorce your wife.

James at first refuses. So Jack and Anne, they look at each other and they're like, f it, you know, who cares? We don't even need your approval. We were just trying to be polite. And they end up getting married or they elope. They're pirates, there it, you know, who cares? We don't even need your approval. We were just trying to be polite. And they end up getting married. Or they elope. They're pirates. There's no rules. They can do that. So after they elope, they decide to get the hell out of town and in order to slip away without

anyone noticing, Anne taps into her childhood days and she goes full Andy. She dresses completely like a man, okay, and when people and like just like when she was a kid people would just buy it. Ann leaves with Jack and joins his pirate crew. They don't want to risk anyone knowing what's going on so they don't even tell the pirate crew on the ship about Ann being a woman, okay? Her name is now Andy. I know my first question, and I know this is like so left field maybe, but my first thought was what happens when you're on your period? Like how do you keep that a secret? Just stuff your pants as best as you can? I guess you

could keep it a secret, but it would suck, you know? Either way, Anne or Andy was like a valuable member of the crew. And this was allegedly proven in 1720 when Jack's ship raids another ship and takes some of the crew hostage. Now the next part of Anne's story is mostly based on a book by Captain Charles Johnson called A General History of Pirates but he didn't know them personally so like many of the stories are based on just pirate legend, I guess. But here's what allegedly went down. Jack sends Anne to seduce the kidnapped pirates, you know, to make them cooperate better, I guess. I mean, it would work, I think, I don't know.

So Anne, she takes off her ante outfit and gets to work seducing the men one by one. She's like, oh my gosh, do you like a shoulder? What about an ankle? Have you seen an ankle, Mr. Pirate Man? My wrists are so delicate and small. That's how I flirt. Um, so they're like, Oh yeah, show me that ankle. Until one of the pirates refuses to cooperate. So Anne is like, are you into men? Cause I could get some of that on you.

She's like, just doing everything she can to seduce him. But this pirate is just resisting. Like he's clearly uncomfortable. Well, so Anne is putting on the move. She's like, yeah, yeah, yeah. Anything? Nothing? No boner?

Okay. Suddenly this person that she's trying to seduce rips open their shirt. I know, I was like, okay. Guess what pops out? Titties. She's like, oh shit. The pirate was a woman just like Anne.

What are the chances of that? Her name was Mary Reed. Anne makes Anne promise she'll keep her secret. She's like, dude, I'm a monkey, don't tell anyone, okay? Uh-huh, uh-huh. So Anne is like, don't worry, I got you. No wonder you weren't turned on. I forgive you now.

They're in the same boat, you know, literally. So the two actually become close friends. Many believe they took things to the next level and became lovers because they were spending a lot of time together. Apparently they were spending so much time together that Jack starts to get a little jealous, okay? And even a little pissed. So according to rumors, Jack breaks into Mary's room one night and pulls out a knife to slit her throat.

Remember, nobody knows that Mary is a woman, so he's getting jealous thinking that Mary's a man, okay? So Mary's in bed like, wait, wait, wait, no, I'm a woman. Jack, I have boobs. I have boobs. You know, trying to show Jack like, I have boobs. I have boobs. Yeah, I'm trying to show Jack like I'm a woman. And Jack is like, oh, like shocked, obviously, okay.

He's like, let me make sure. I think, yeah, you must be a woman. Now we don't know if he confronted her about like how much time she was spending with Ann, but because she was a woman, Jack spares Mary. I'm sure he was actually relieved because he was thinking like Mary and his girl were having an affair, you know? So he's probably like, oh my God, that's crazy.

My bad. Now despite the secrets, Anne and Mary are an incredible team. They're like Mary-Kate and Ashley of pirate ships, okay? The two of them, along with Jack, decide to expand their pirate operation and make it even bigger. I've been trying to lock down a better morning routine. So for me, that means waking up early, boo,

making sure to eat breakfast, mm, staying hydrated, mm, and then going on like a walk, mm. So I've been on this journey to find new deodorant. I'm always looking for deodorant that's like more natural ingredients and all that stuff, you know, so I've tried many. And a lot of them, no offense to you guys, natural deodorant companies out there,

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I know someone out there is gonna relate to this. The under boob sweat. Yeah, so you put it down there, okay? Anyhow, with Lumi, they have scents like lavender sage, toasted coconut, and clean tangerine. I usually go for clean tangerine, but they all smell really great. Now Lumi surprised me when it came to odor control.

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Math, use code darkhistory for 15% off your first purchase at lumideodorant.com. That's code darkhistory at L-U-M-E-D-E-O-D-O-R-A-N-T.com. Please support our show and tell them we sent you. Smell fresher, stay drier, and boost your confidence from head to toe with Lumi. So Ann, Mary, and Jack were absolutely killing it as being pirates.

They got off to a rocky start, you know. Eventually they figured it out and they made a great team. And they wanted to expand their pirate operation so they could increase their wealth. So Jack takes the ship back to the Bahamas where he and his crew steal a new ship called the William. After stealing the ship, they gather a new crew and set out to sea.

Now at this point, there's no hiding that Anne and Mary were women. They just like stopped fully disguising themselves. We don't know the exact details of it all but they stopped and they ended up becoming like high ranking members of the crew despite their gender. For months in 1720 their ship causes absolute terror all over the Caribbean taking down ships and raiding villages. Anne and Mary work really well together as a team. I mean, they're both fearless and they share the dirty work. Most importantly, they knew how to fight.

Oh yeah, they were each known to carry a machete and a pistol. And since they were high ranking members of the crew, they were even allowed to order prisoners to be murdered. Jack, Anne, Mary, and the crew raided at least 10 ships in just the month of September of that year alone. Now these missions were mostly led by Ann and Mary. They're raiding towns for their goals and even taking prisoners for ransom. Ann and Mary especially, they were were like they were just ruthless. One of

the prisoners later described them as very active on board and quote willing to do anything when people saw the William out on open water. They were terrified because they knew that ship did not fuck around. But in October 1720, Anne, Mary, and Jack end up on a quote unquote wanted pirates list in the Boston Gazette. So now there was a price on their heads. On top of that this crew had also made a ton of enemies. They pissed everyone off along the way so things were just starting to go downhill really fast. In the same month, their ship is attacked by another government ship

and the government came armed and ready to fight this crew. I mean, the William had such a terrifying reputation. They weren't going to take like any chances. But when the government's crew jumps onto Jack's ship, no one fights back. Apparently the entire crew was absolutely plastered and they were all hiding in fear below deck. I mean if you're gonna go out, I'd go out drunk too, why not?

So these people, the crew, everyone was just caught drunk-handed. Apparently the only people who fought back were Anne and Mary. At some point, Mary gets enough time to stop and yell to the men quote, if there's a man among ye, you come up and fight like the men ye are to be, ye. And I guess no one answers, just crickets. She's like, all right, great. So Mary, she's like, you know what, you guys are pissing me the hell off. So she ends up firing her pistol into the ship at her own crew.

Yeah, she kills one of the men. Hopefully that will wake them up, you know, by shooting into your men, it'll get them to maybe get it together. And yeah, so she kills the guy and she's like, F you guys, whatever. She goes back into battle. Mary and Anne, they fought a good fight, but at the end of the day, it was just two of them against an entire crew.

So everyone gets captured and put on trial in Jamaica. All of the men, including Jack, get immediate sentences to be hanged because they're women. Anne and Mary's cases are taken to trial. But Mary and Anne, they were well known violent pirates. So nothing they could say or do would make the jury be on their side.

So they go to court, they do the thing, blah, blah, blah. Jury comes back with a verdict. Anne and Mary are sentenced to death by hanging. People during this time were cheering like, yeah, kill the pirate girls, blah, blah, blah. Then Anne and Mary drop a bomb. They look at each other, then turn to the jury. Well, what about our children?

Well, you mentioned a child and bitch, the audience goes wild. Legend has it that both women were pregnant by Jack. Pregnancy was kind of like a get out of death free card, you know, because the key people, you know, the jury decided to let them plead their bellies, AKA wait out their pregnancies in prison rather than be sent to death.

Okay, loophole, love that. So they go to jail, whatever, and sadly sadly Mary dies from illness not long into her prison sentence. She's out. Anne, on the other hand, disappears. The ending of her story is a complete mystery. We don't know if she gave birth. Hell, we don't even know if she was really pregnant. We don't know if she died around the same time as Mary. We don't know. Her name stops appearing in any documents after she gets sent to prison.

So rumor has it, Anne was broken out of the prison and smuggled to America back to her father. The idea is popular because of a book inspired by Anne's life called Mistress of the Seas. What we do know is that there was no recorded execution of Anne, she was just gone, disappeared. I like to think that maybe Anne escaped from jail and found herself churning butter somewhere,

just living a normal life, thinking about like her wild, crazy pirates days, you know, but playing, pretending to play normal, my fantasy. Here's what I learned. I have been told all my life that pirates were drunk sloppy men but nae nae that is not true. There are many women who were very powerful leaders on the sea that nobody seems to talk about and honestly I don't see why they don't. These make some great stories, okay?

I'm waiting for a movie. I would watch this one. I don't like pirate movies, but sorry, don't come for me. I'll go on Pirates of the Caribbean, the ride, only because it's hot outside and that place is really cool. Like it's cool, like, AC. But the ride is kind of boring and it smells, sorry.

People love that ride, I don't get it. I'm like, whatever. Listen, we can talk about pirates all day, every day. So if you want a part two, let me know down below. I would love to do that because I learned so much. I don't care about, which is sad to say, but I don't care about like the men's side of stories when it comes to pirates.

But for some reason, the women's side is really interesting. Is that sexist? Well, anyhow, hopefully they'll be bleep-blah-bloop, fill in the blank, bye. Our next episode, we're going to be talking about one of the most controversial cities in America. Many people refer to it as the party capital of the world. That's right.

We're talking about Sin City. What happens in Vegas stays in Vegas. And it got me thinking, like, how the hell did one town in the middle of the desert become one of the most famous places in the world? Join me next time when we talk about the dark history of Las Vegas. Yeah. I'll be wearing the same thing. Sorry about that. I'd love to hear your guys' reactions to today's story, so make sure to leave a comment down below

so I can see what you guys are saying, and your comment might even be featured in a future episode. Now let's read a couple of comments you guys have left me, yeah? Laura Riley 308 left me a comment saying, respect your work, Dark Bailey. Thank you, Laura.

You know, I've been called a lot of things, but no one ever has called, Dark Bailey. Thank you, Laura. You know, I've been called a lot of things, but no one ever has called me Dark Bailey. I'll take it, I'll take it. Thank you so much, thank you. We put in a lot of time and thought and energy into these episodes, and I appreciate you for acknowledging all of the hard work. Maisie Days Nine left me a comment saying,

my guinea pig and I never miss an episode. Maisie I love that for you. What's your guinea pig's name? Cute! I love that name. Um how old? What is it? I don't know what a guinea pig is. I would like to get one though. Anyways I love that and I hope you guys are having like a cute little like matching pajamas. You and the guinea pig and then you can watch. Please send me a picture. Thank you. JustyCasBurrRyTight7252 left us an episode suggestion. Aloha Bailey, thank you so much for your history lessons. Also, may I suggest a topic for another dark history? Video games, brutal ones.

Does it increase violence or decrease? You are the best. Oh my gosh, aloha. Are you in Hawaii? Where? Semi picks, what's it look like? Can I come over? Let me know, invite me. Invite me over to your houses, god damn it. I? Can I come over? Let me know, invite me.

Invite me over to your houses, god damn it. I'm trying to come visit. Need to get out of here. Going crazy. Just a girl stuck in a box on YouTube. They won't let me in. Anyways, Aloha! Hi, great idea.

I know nothing when it comes to modern day video games, but I think it could be an interesting deep dive because I know they've done studies, right, about the brain if people if it does have an effect and that could be a really interesting conversation. I stick to Mario Kart. Yeah, that's where I'm at. Anywho, thank you for the suggestion. I really appreciate it and I love love when you guys suggest stuff.

Love it. So keep it coming. Thank you guys for watching and engaging. I appreciate you. Love it, so keep it coming. Thank you guys for watching and engaging. I appreciate you. Keep on commenting because maybe you'll be featured or maybe you won't, but I love it either way. Did you know you can join me over on my YouTube where you can actually watch these episodes on Thursday after the podcast airs? And while you're there, you can also catch my murder, mystery, and makeup.

Oh, and don't forget to subscribe because I'm here for you all the time. And hey, if you don't know, Dark History is an audio boom original. Special thank you to our expert, Laura Suk Duncombe, author of Pirate Women and a Pirate's Life for She. That's good. And I'm your host, Bailey Sarian. I hope you have a good day, you make good choices,

and I'll be talking to you guys soon. Goodbye. Ooh. Ooh. Ooh. Ah.