Anne Bonny [pirate]

Calvin

Welcome to the infamous edition of the Headstones and Microphones where we use AI to step into the past through a researched, first-person simulation done through creative story telling of history's most infamous people. Now, let’s meet our guest.

Calvin

"Welcome to the podcast. Let’s start at the absolute beginning, where the public narrative hasn’t yet distorted who you were. When and where were you born, and what was your given name?"

White Female Guest

"I was born near Cork, Ireland, around the late 1690s. My given name was Anne McCormac. I was born out of wedlock to a lawyer named William McCormac and our family maidservant, Mary Brennan. Because of the scandal in our town, my birth wasn’t exactly something celebrated by polite society."

Calvin

"What was your hometown and home life like as a child?"

White Female Guest

"My early childhood was a bit of a mess due to the public shame of my birth. To avoid the local gossip, my father actually dressed me up in britches and tried to pass me off as a boy, claiming I was a relative's child he was training to be his legal clerk. Eventually, his wife discovered the truth, which ruined his legal practice in Ireland. He threw caution to the wind, took me and my mother, and we sailed across the Atlantic to Charles Town in the Province of Carolina to start over. He dropped the 'Mc' from our name to fit in, and he became a very wealthy merchant and plantation owner. Sadly, my mother passed away when I was just twelve years old, leaving me in a big house with a father who had a lot of money but not much control over me."

Calvin

"Was there a story behind your name, or a nickname that stuck with you?"

White Female Guest

"When my father was trying to hide my identity from his wife and the townspeople back in Ireland, he called me 'Andy' to make the boy disguise stick. Later on, after I married a penniless sailor against my father's wishes, I took his last name, and that is how the world came to know me as Anne Bonny."

Calvin

"What were you like as a child, and how many years of schooling did you actually attend?"

White Female Guest

"I didn't have much formal schooling, as I spent my time roaming around Charles Town. I grew up with a fierce, independent, and courageous temper. The townspeople spread wild stories about me—saying I once stabbed a servant woman with a kitchen knife in a fit of passion, or that I beat a grown man so badly he was ill for quite a while. While those stories might have been exaggerated by local gossips, I certainly wasn't a proper Southern lady. I was rebellious, headstrong, and entirely unmanageable."

Calvin

"What’s a decision that changed everything for you, but felt small at the time?"

White Female Guest

"It was choosing to marry James Bonny. He was a small-time, penniless pirate-wannabe who didn't have a cent to his name. I thought it was a grand romance and a way to escape my father's expectations. But that choice ruined my relationship with my father completely. He was so furious that he disowned me entirely and kicked me out of his house, cutting me off from the massive fortune I stood to inherit. With no money and nowhere else to go, James and I packed up and headed for the pirate haven of Nassau in the Bahamas."

Calvin

"Let's talk about your early run-ins with the law. Before the world knew your name for your most infamous actions, what was your very first arrest or interaction with law enforcement, and what were the consequences?"

White Female Guest

"My first official trouble with the authorities happened in August 1720 in the Bahamas. Governor Woodes Rogers issued an official proclamation that named me explicitly as a fugitive. I had abandoned my husband James—who turned out to be a snitch for the governor anyway—and teamed up with John 'Calico Jack' Rackham. Together with Mary Read and a small crew, we stole a swift sloop named the William right out of Nassau Harbor. That grand theft put a massive target on my back and made me an outlaw in the eyes of the British Empire."

Calvin

"At what moment did you realize your name would never be forgotten?"

White Female Guest

"It was during that autumn of 1720 when our exploits on the William became the talk of the Caribbean. We were tearing through the waters around Cuba and Jamaica, capturing small fishing vessels and merchant sloops. The regional newspapers and government notices began publishing accounts of our crew, specifically highlighting that two women were sailing, stealing, and fighting alongside the men. Hearing that the British authorities were actively dispatching pirate hunters specifically to track us down made it clear that our names had broken across the colonies."

Calvin

"Did fame make you more dangerous, or did it simply expose who you already were?"

White Female Guest

"The notoriety just exposed the fire that had been burning inside me since I was a child in Carolina. When we were out on the high seas, I finally had the freedom to act on my own terms. During engagements, Mary and I would wear men's jackets, long trousers, and tie handkerchiefs around our heads to join the boarding parties. I handled the weapons, helped secure the captured ships, and used language just as foul as any man on board. The open ocean didn't change my spirit; it just gave me a canvas big enough to display it."

Calvin

"Who do you believe betrayed you first: a person, society, or your own instincts?"

White Female Guest

"My first husband, James Bonny, was the ultimate betrayal. I married him thinking he shared my rebellious spirit, but once we got to Nassau, he turned into a spineless informant for Governor Rogers, turning in fellow pirates for a bit of favor. When I fell in love with Calico Jack, Jack even offered to buy out my marriage license to give James a legal separation, but James refused and ran straight to the governor to complain. He chose the structure of a hypocritical society over loyalty to me."

Calvin

"What was your most unique habit or a random fact about you that would surprise people?"

White Female Guest

"People are always surprised to learn that Mary Read and I kept our identities as women completely open to our regular crew. The stories claim we disguised ourselves as men the entire time, but the truth is we only put on the heavy jackets, trousers, and weapons when we were actively going into battle or capturing a ship. On a regular day cooking and working the deck, everyone on the William knew exactly who we were."

Calvin

"What did the public never understand about the pressure you were under at the time?"

White Female Guest

"During our trial in Jamaica, the witnesses testified about how aggressive and relentless we were during the raids. What the public didn't understand was that as women in a completely male-dominated world, we couldn't afford a single moment of weakness. If we showed even a shred of hesitation or fear, we would lose the respect of our crew and our authority on the ship. We had to be twice as fierce just to be treated as equals."

Calvin

"Did you have any known rivalries that defined your career?"

White Female Guest

"Our main adversary was Governor Woodes Rogers of the Bahamas. He was determined to clean up Nassau and wipe out the Golden Age of Piracy. He used my husband James as a pawn and put out the bounties that chased Jack, Mary, and me across the Caribbean. Every single sail we spotted on the horizon felt like an extension of Rogers trying to pull us back into a cage."

Calvin

"What personal battles were you fighting privately while the world was watching?"

White Female Guest

"While we were actively raiding ships and evading the British Navy, I was dealing with a secret pregnancy. Running a ship, hauling ropes, and preparing for combat while carrying a child is a physical burden the historical texts rarely emphasize. It added a ticking clock to everything we did, knowing that a chaotic pirate sloop was no place to bring a newborn into the world."

Calvin

"What was your darkest moment, and was there ever a time you wanted to walk away from it all?"

White Female Guest

"The absolute darkest moment came in October 1720 off the coast of Jamaica. A pirate hunter named Captain Jonathan Barnet caught our ship by surprise. The crew had been drinking heavily the night before and were completely incapacitated. When Barnet’s men boarded us, almost all the men, including Jack, cowarded out and hid below deck. Only Mary Read, myself, and one other crew member stayed on the deck to fight off the attackers. I was screaming at the men to come up and fight like humans, but they wouldn't budge. We were completely overwhelmed and captured because our own crew lacked the spine to stand with us."

Calvin

"When the law finally closed in, how exactly were you brought to justice? Walk me through the final arrest, the charges that ultimately stuck, and the legal outcome of your trials."

White Female Guest

"After Captain Barnet captured us, we were taken to St. Jago de la Vega in Jamaica to face trial under Governor Nicholas Lawes. The charges were piracy, robbery, and felony on the high seas. The trial was swift, and the court found us guilty. Jack and the other men were sentenced to hang immediately. Mary and I were also sentenced to death by hanging, but when the judge asked if we had anything to say, we both 'pleaded our bellies.' Because we were both visibly pregnant, British law forbade the execution of an unborn child, so they granted us a temporary stay of execution and sent us back to the prison cells."

Calvin

"What’s the craziest rumor ever told about you, and what part of your story has been exaggerated the most?"

White Female Guest

"The grandest exaggeration is the absolute mystery of what happened to me after that trial. Because the official pirate logs and execution records in Jamaica stop mentioning my name after my reprieve, people invented wild folklore. Some say I died of a fever in that damp prison, others say I escaped and went right back to piracy under a new name, and some romanticized that my wealthy father used his political connections to ransom me and bring me back to the Carolinas to live out a quiet life. The truth disappeared into the archives."

Calvin

"Anne, do you have any closing remarks about the interview or the stories you shared that you would like to share with the listeners before signing off?"

White Female Guest

"I would just tell your listeners that history is often written by the people who hang you. They wanted to paint me as a lawless monster, but I was just a person who looked at the narrow options women had in the 1700s and chose a life of absolute freedom instead. Think for yourselves, and don't let the world lock you into a life you didn't choose."

Calvin

"And that wraps up another conversation from beyond the grave. Thanks for joining us on The Headstones and Microphones Podcast. Remember—Do better with the life you have been given and choose to do good in this life. Please help spread the word by sharing and following the pod."