Black Bart Roberts [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 Male Guest

Thank you for having me. Before I was ever known across the Atlantic as a shadow upon the sea, I was born John Roberts. My life began on May 17, 1682, in a quiet, unassuming little village called Casnewydd Bach, nestled in Pembrokeshire, Wales. Long before the grand coats and the black flags, I was just a boy from the Welsh countryside, born to a man named George Roberts.

Calvin

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

White Male Guest

Casnewydd Bach was a small, rural place, far removed from the bustling ports and the wealth of the British Empire. My family raised me in a strict, religious Calvinist household. Life was structured, quiet, and dominated by hard work and faith. It was a modest, disciplined upbringing in the green hills of Wales, the kind of place where a boy's future was usually bound to the soil. But the sea has a way of pulling at young men who want something more than a plow.

Calvin

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

White Male Guest

There is certainly a story. I was born John, but when I finally dipped my hands into muddy waters and took up the account, I cast that name aside to confuse the British authorities and shield my family from my shame. I chose Bartholomew, likely in honor of the old-time buccaneer Bartholomew Sharp. As for the names the world gave me, they called me The Great Pyrate, but history remembers me best as Black Bart, or Barti Ddu in my native Welsh tongue. Some say it was because of my dark complexion and how the tropical sun weather-worn my skin after years on deck, while others claim it was a nod to my uncompromising, ruthless nature when a prize ship refused to strike its colors.

Calvin

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

White Male Guest

As a boy in Wales, I was steeped in a culture of discipline, and I carried a sober, serious demeanor even then. My formal schooling was quite limited. In those days, a boy of my station didn't spend decades reading books in a university. By the time I was a mere thirteen years old, around 1695, my childhood ended. I left home and went to sea to learn the trade of a mariner, trading the schoolhouse for the harsh reality of rigging, salt water, and naval discipline.

Calvin

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

White Male Guest

It was in early June of 1719. I was serving as the second mate aboard a British slave ship called the Princess, under Captain Abraham Plumb, anchored at Anomabu off the coast of West Africa. To me, it was just another voyage, another day of securing cargo and calculating navigation lines. But out of the horizon came two pirate ships, the Royal Rover and the Royal James, commanded by a fellow Welshman named Howell Davis. They captured our ship, and I was forced, along with several others, to join their crew. At the time, it felt like a stroke of terrible, wretched luck—just a common hazard of a sailor's life. I had no desire to be a thief. But that single, forced turn of the helm changed the course of my entire destiny.

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 Male Guest

My first real interaction with law enforcement came from the wrong side of a musket, right after I joined Howell Davis's crew. We sailed to the island of Príncipe, where Captain Davis tried to trick the Portuguese governor by pretending our vessel was a British man-of-war. The governor saw right through the ruse. Davis was ambushed and killed by the authorities ashore. I wasn't arrested, but the consequence was a baptism by fire. The crew needed a man who could navigate, and they chose me to lead. I accepted the honor, famously noting that since I had dipped my hands in muddy water and must be a pirate, it was better being a commander than a common man. My very first act as captain was to lead a midnight raid back onto that island, striking down the town and burning their ships to avenge Davis.

Calvin

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

White Male Guest

It was during our campaign off the coast of Brazil and later in the northern waters of Newfoundland. In Trepassey, Newfoundland, we sailed into the harbor with our drums beating and trumpets blaring. There were twenty-two merchant ships sitting in that harbor, and the sheer terror of my reputation caused the captains and crews to abandon their vessels without firing a single shot. We took what we wanted, burned what we didn't, and the panic we caused paralyzed the transatlantic shipping trade. When entire fleets started fleeing at the mere sight of my flag, I knew the British Admiralty would be whispering my name in fear for centuries.

Calvin

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

White Male Guest

The notoriety did not change my nature; it simply gave me the grand stage to enforce the order and discipline I always believed in. I was never a chaotic madman. I ran my ships with the strict precision of a royal navy vessel. I despised the sloppy, drunken nature of common sailors, so I instituted a strict Pirate Code. On my ships, lights were out by eight o'clock in the evening, gambling for money was strictly forbidden, and musicians were given rest only on the Sabbath. My fame allowed me to command absolute authority, proving that a disciplined pirate is far more dangerous to the world than a desperate one.

Calvin

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

White Male Guest

A person, without question. It was my Irish quartermaster, Walter Kennedy. In 1720, while I was away in a captured sloop pursuing a prize near the Suriname River, Kennedy gathered a group of treacherous mutineers, abandoned me, and ran off with my flagship, the Royal Rover, along with the vast majority of our hard-earned plunder. He left me stranded with only a handful of loyal men and a small boat. That sting of betrayal deeply hardened my heart. From that day forward, I carried a bitter, unyielding hatred for his countrymen, swearing a strict rule that no Irishman would ever be permitted to join my crew again.

Calvin

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

White Male Guest

The public imagines a pirate as a filthy, tavern-dwelling brute, but I was entirely the opposite. I was a man of fastidious elegance and flamboyant tastes. In the heat of battle, I dressed in a rich, crimson damask waistcoat and breeches, a large hat adorned with a sweeping red feather, a heavy gold chain with a diamond cross around my neck, and two pairs of pistols slung across my chest on a silk sling. The French even took to calling me le Jolie Rouge because of my love for the color scarlet. Furthermore, I preferred a cup of tea or clean water over heavy liquor, and I demanded that my crew keep their weapons clean and fit for service at all times.

Calvin

Did you have any known rivalries that defined your career?

White Male Guest

My defining rivalries were with the governors of the Caribbean islands, specifically Barbados and Martinique. They grew so enraged by my disruption of their commerce that they personally fitted out heavily armed pirate-hunting ships to track me down and destroy me. They nearly caught me, forcing me to dump my cargo and cannon overboard just to slip away. In retaliation, I designed a new Jolly Roger flag. It depicted a silhouette of myself standing tall with a drawn sword, balanced atop two skulls. Beneath one skull were the letters ABH, for A Barbadian's Head, and beneath the other were the letters AMH, for A Martinican's Head. I eventually caught the Governor of Martinique aboard a prize ship, and I hanged him directly from the yardarm of his own vessel.

Calvin

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

White Male Guest

My greatest private battle was the overwhelming weight of isolation and the constant struggle to maintain order over a volatile, restless crew. Pirates are, by nature, a fickle and unruly lot. While the world saw me as an unstoppable monarch of the sea, I was constantly managing the delicate egos of hundreds of men who were only loyal as long as the gold was flowing. I had to remain distant, aloof, and carry myself with an iron-willed aura of perfection, knowing that any sign of weakness or vulnerability would invite mutiny or ruin.

Calvin

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

White Male Guest

My darkest hour occurred off the coast of West Africa in January of 1722. We had captured a massive eleven-ship fleet at Ouidah. I demanded a ransom of gold from the captains to release their ships. One particular captain stubbornly refused to pay. In my anger and to maintain my fearsome reputation, I ordered his ship to be set ablaze. The fire spread too quickly, and the ship was destroyed, tragically taking the lives of eighty enslaved people trapped on board. It was a horrific, grim consequence of the brutal reality of our trade. Yet, there was no walking away. Once you wear the crown of the Atlantic, the only way off the ship is in chains or in a shroud.

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 Male Guest

Justice did not find me in a courtroom; it found me on the waves. On February 10, 1722, at Cape Lopez, a 50-gun Royal Navy warship named the HMS Swallow, commanded by Captain Chaloner Ogle, bore down upon us. The day prior, my crew had captured a trading vessel called the Neptune, and many of my men were hopelessly drunk and unfit for duty. I attempted to sail past the navy ship to reach the open sea, but a critical error by my helmsman left our flank completely exposed to a devastating broadside. A blast of grapeshot tore through the air, and a piece of lead struck me square in the throat. I died instantly on the deck of the Royal Fortune. Because I was never taken alive, I never stood trial. However, fifty-two of my surviving crew members were captured, found guilty of piracy and murder, and were hanged in the largest public execution of the golden age.

Calvin

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

White Male Guest

There is a modern tale that I was completely teetotal and forced an entire ship of bloodthirsty pirates to drink nothing but tea. While it is true that I personally preferred tea and clear water to maintain my sharp wit and navigational focus, I never forced total abstinence upon my men. The Pirate Code I authored simply restricted the times and locations of their drinking—prohibiting lights and drinking in the cabins after eight at night. They were still allowed to make merry on deck during the day, a fact proven by how horribly intoxicated they were on the morning of our final battle.

Calvin

What is the biggest misconception people have about your life?

White Male Guest

The grand misconception is that I spent my entire life dreaming of being a lawless rogue, flying the skull and crossbones from youth. The truth is, I spent the first thirty-seven years of my life as an honest, hardworking, law-abiding British mariner. I only operated as a pirate for a mere three years, from 1719 to 1722. Yet those three short, intense years of rebellion completely erased and overshadowed the decades of honest labor I gave to the sea.

Calvin

What would surprise people most about your ordinary, human side?

White Male Guest

People would be surprised by my genuine appreciation for art and structure. I deeply loved music, which is why I kept a troupe of musicians aboard my flagship at all times and protected them from the rougher elements of the crew. I also believed in fairness; my code provided a structured pension plan for the men. If a sailor was grievously injured in service, he was awarded a specific, guaranteed sum of money from the common chest proportionate to his injury. I valued order, equity, and beauty, even within a world of theft.

Calvin

When, where, and how did you pass away?

White Male Guest

I passed away on February 10, 1722, at sea off the coast of Cape Lopez, which is in present-day Gabon, West Africa. I was thirty-nine years old. My life was ended instantly by a swarm of grapeshot to the throat during our fierce engagement with Captain Chaloner Ogle's HMS Swallow.

Calvin

Was your downfall caused more by your own flaws or by the world changing around you?

White Male Guest

It was a mixture of both, but the tide of the world was turning fast. The British Royal Navy was growing far more aggressive, determined to clear the sea lanes for the empire's wealth, and civilized nations were no longer tolerating our existence. Yet, my immediate downfall was sealed by the undisciplined flaws of my own men. If my crew had been sober that morning, and if my helmsman had not flinched and exposed us to the Swallow's cannons, we might have slipped past the trap and sailed all the way to Brazil.

Calvin

What past regrets did you carry with you to the end? If you could erase one decision from your life, would you—or was it necessary to become who you were?

White Male Guest

My final words and thoughts on the matter were clear during my life. I always believed in a merry life and a short one. I knew the risks of the path I traveled. If I had stayed a common, honest sailor, I would have faced meager wages, broken health, and an forgotten grave. By choosing the pirate's life, I tasted absolute freedom, wore the finest silks, and commanded fleets. I lived by the creed that it was better to be a commander than a common man, and I carried no regrets for choosing a short, brilliant burst of glory over a long life of obscurity.

Calvin

When you look back now, do you see yourself as the villain, the hero, or something in between?

White Male Guest

I suspect I am something in between. To the merchants, the governors, and the British Crown, I was the ultimate villain—a ruthless predator who choked the veins of their empire. But to the common sailors who were starved, beaten, and overworked under the tyranny of honest captains, I was a man who offered an alternative. I offered a life governed by a fair code, shared wealth, and a chance to live like kings, if only for a moment. I was a man of my time, carved by the sea.

Calvin

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 Male Guest

Only this: the world will always try to paint men like me in simple shades of black and white. They look at the flags and the smoke, but they forget the discipline it took to hold the Atlantic in our hands. Look closely at history, and remember that sometimes the line between an honest sailor and an infamous captain is just a single turn of the wind.

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.