Hoist the Colors

who were the pirates and what were they after?

Authoritarianism has ebbed and flowed through Western history, and in its more ascendant periods has always come a strong reaction. Rebellion. A journey to the borders and beyond. Welcome to the realm of the western pirate, namesake of this little island on the internet I write from. When Ryan McEntush pitched me a literary history of the phenomenon I had to say yes. It’s a beautiful, perfect Sunday read. Enjoy.


Images of peg-legs, eye patches, and decrepit criminals seeking buried treasure come to mind. While this depiction might be unique, the uncivilized and disillusioned subsiding on the outskirts of an empire is nothing new. Through strife, these barbarians grow feral, and their ideas bleed into the mainstream. Struggle as they must, one day they approach the gate.

As 14th century historian Ibn Khaldun observed, this is a perennial conflict. With time, he suggests, civilization grows decadent, only to be conquered by a new zeitgeist or social group from the periphery. Though this observation was made while studying the nomadic peoples of Northern Africa, Khaldun makes a prescient claim about the nature of history itself. Hardened by the harsh conditions of the fringes, the barbaric provides a compelling new vision, or in his words, asabiyyah.

The frontier bestows power to those who conquer it. For early Americans, greenfield opportunity presented a life free from nobility and despotic rule, and laid the framework for a nation that promised liberty. We manifested this destiny and molded a world power from hardened ambition. That said, not all are successful in securing sovereignty. This is the remarkable story of those that failed; the pirates of Nassau.

Stormy Seas

In the Age of Discovery, European powers spread their tentacles across the world, seeking new riches as far as the wind would take their sails. Maritime trade was the ichor of their blossoming coffers, yet even in their supremacy, precious blood was spilled.

Like Cain, a singular figure would catalyze an era of violence— Henry Avery. In 1695, Avery ascended to infamy after his sacking of the Grand Mughal’s Treasure Fleet on its journey home from Mecca, a staggering $130 million prize in today’s dollars. Livid at this transgression, the Mughals believed Avery to be sailing for the British Empire, leaving Parliament scrambling to repair this critical trade relationship. A group of Avery’s men were finally hunted down and a grand trial was put on for the world to witness how strongly the British Empire disavowed piracy. Yet, even with insurmountable evidence of the pirates’ culpability, the jury did not convict them. Reputation at risk, the Crown bent the law to re-try the pirates, no longer underestimating the populist appeal of the Henry Avery legend that had spread through pamphlets and ballads. This time they were hung for their crimes. Though Avery himself was never captured nor seen again— a happily ever after etched into maritime mythology.

To fathom why many would admire a pirate, you need to understand what life was like for the average sailor. If you were lucky enough to be on a merchant ship, you were promised wages of £33/year at a time when a pound of beef was £0.2/lb. If you weren’t lucky, you’d get picked up by a press gang, a group tasked to forcibly enlist seaworthy individuals into the navy. The poor were particularly easy targets, and victims would sow wages of only £15/year. No matter what ship you were on, the reality was even bleaker. On any voyage heading to the West Indies, the crew fatality rate could reach 50%. Even if you returned home, you often received a trifle of what you were owed, or were pressed onto another ship before you could leave the docks. Vessels weren’t much more than floating cesspools of rot and disease, and it wasn’t uncommon for captains to severely abuse their crew. Yet, for many, the call of the sea was too strong and opportunity too great, so away they sailed.

It was this crucible that morphed a young Avery from ordinary sailor to pirate captain, leading a mutiny and commandeering a ship after wages were withheld. The newly christened vessel, the Fancy, prowled the Indian Ocean and sanctified its common anchorage, Madagascar, as a pirate lair. In later years, after his historic score, Avery’s evasion of British authorities took him to the edge of the empire— forever changing a small island settlement in the Caribbean.

With enemies scouring the Indian Ocean, Avery fled straight for Nassau, the largest settlement on the most isolated, British-friendly island in the West Indies. And “large” is relative — the docking ofthe Fancy nearly doubled the town’s population. It was there in the outskirts of civilization that he figured no one would immediately recognize them. Upon anchoring, he took on a fake identity and bribed the locals just to be sure, allowing him to discard his legendary ship, fence spoils, and safely part ways with his crew. Still, stories of Henry Avery, king of the pirates, would permeate society for years to come, and would deeply resonate in the minds of a new generation beginning their lives at sea.

For struggling sailors wallowing below deck, Avery represented hope. As his legacy echoed across the world, so too did the dream of a life outside the grasp of institutional powers and navy frigates. The apocryphal Libertalia, a pirate den believed to be the Madagascan anchorage of Avery himself, depicted this aspiration for something greater. A place where, according to legend, “every man was born free, and had as much right to what would support him, as to the air he respired”. Composed of men said to be “vigilant guardians of the people's rights and liberties”, standing steadfast as “barriers against the rich and powerful”. While Libertalia was fiction, those inspired would seek to make it reality.

Years after Avery's departure, the crystal clear Nassau waters would again host outsiders, this time turning the sea red with carnage. In 1703, the War of Spanish Succession drove a small Franco-Spanish fleet to ransack the fledgling town, and vessels hunted the surrounding Caribbean waters. For those that dared, this brought a resurgence of the privateer, or rather a ship with a “letter of marque” giving them legal permission to ransack enemies of their state. Life as a privateer was more dangerous than other maritime professions, but it presented much greater reward for skilled individuals. A single score might yield a lifetime’s wages, so it’s understandable that when war ceased in 1713, privateers were reluctant to go back to their tawdry past lives. Many continued raiding ships, and for this deed they were branded pirates and subject to the wrath of the empire.

The Rise of Nassau

While previously welcomed as privateers, anyone caught sheltering pirates would hang. This left many scrambling for whatever safe harbors they could find — leading some in the footsteps of Avery to the shores of Nassau. The ruins of the town lay bare across the beach, and legend tells of the Fancy’s remains peaking over the lapsing surf. Plans to rebuild from the ashes were quickly hatched. 

Pioneering the early effort was Benjamin Hornigold, an old privateer among the first of this new generation to arrive in Nassau. Hornigold began his piracy in simple canoes and was shockingly successful, in time, growing his small band into a respectable crew. Each successful raid would bring new goods and materials to the budding town, and Hornigold would find his captaincy extended into a pseudo-governorship of Nassau’s growing number of shacks strewn across the sand. Meanwhile, another figure sought a single score that would altogether breathe new life into the settlement.

At the time, Spain’s riches were mined in the New World, taken by caravan to the coasts of Central America and Mexico, then sailed in massive treasure fleets to the motherland. Every pirate was aware of this, but none were able to deploy a force strong enough to confront it head on. But in 1715 they didn’t have to...a terrifying hurricane battered the Spanish Treasure Fleet, killing 2000 men, wrecking 11 ships, and casting gold bullion and millions of silver pesos across the sands of present day St. Augustine, Florida. Word quickly spread as Spain desperately tried to salvage what they could, perking the ears of ex-privateers. Among them was a man named Henry Jennings.

At first word, Jennings rallied a crew and set sail, but he arrived to find much of the treasure already safely in Spanish hands back in Cuba. What remained lay scattered in the shallow waters or protected in a makeshift fort along the beach — no match for his crew of 300 men. These scraps were still a fortune, and Jennings knew he needed to find a safe place to divvy up the spoils. For this, he chose Nassau. 

Hornigold and Jennings’ first interaction went as well as you’d expect. Jennings’ sizable crew captured one of Hornigold’s canoes, and with no comparable force, Hornigold could only watch and grit his teeth. After what surely amounted to a festival of debauchery in the following days, Jennings craved more and set out once again. He would lead numerous salvages of the Treasure Fleet over the next couple of years and would raid any ship that was unlucky enough to stumble across him. That said, the wrecks brought more than wealth to Nassau’s shores. By the time Jennings had scraped together every piece of lost Spanish treasure, and had every power in the region chasing him down, Nassau was home to thousands.

This gold rush brought people of all kinds, yet their shared experiences bound them. Nassau blossomed into a thriving community of societal outcasts. Beyond dejected sailors, crews were made up of escaped slaves, runaway indentured servants, and otherwise downtrodden members of society. To them, piracy was both an opportunity for a better life and revenge against the elite who had tormented them for generations. 

The town of Nassau itself embodied this, too, having been left for ruin after its destruction in 1703. As the similarly disillusioned swarmed the island, Nassau would enter its grandest days. At its peak, the town was a hub of trade across the Caribbean. It’s harbor uniquely sheltered amongst the shallow waters of the Bahamian archipelago, and whose safe passage was only possible in small, quick vessels—and notably not the navy’s floating fortresses. Atop a hill loomed the crumbling remains of a fort, and nearby the old governor’s mansion stood proud, yet broken. Inhabitants lived amongst the ruins, or thatched together crude dwellings made of sticks and driftwood. Along the beach, crews of men tiresomely scraped the underbellies of careened vessels that basked in the beating sun. Perhaps the only part of town that looked organized at all was near the docks. It was there that arriving mariners traded goods and purchased supplies for their next voyage. Of course, with coin in hand, many would head straight to the taverns. A boisterous scene, rum-drenched breath spat curses of all languages. Loose words would free fists, and across the island all lived by the rule of “the strongest man carries the day”. People simply fended for their own amidst this anarchy. With time, the refuse of modernity piled up and flowed into the dimly lit, overgrown pathways that mazed through structures in varying states of collapse. The town reeked, and was surely not the tropical paradise you might’ve envisioned. These people were outlaws and at odds with the greatest powers in the world, in near constant fear of a Union Jack appearing on the horizon. Nassau was a life in the trenches, but each swig of rum made it tolerable. Yet, their war had a purpose. They were the freest men in the world, and they were willing to do anything to keep the authoritarian institutions that they escaped from away from their nascent utopia. In 1716, population peaked and chaos reached a boiling point. Many proposed that greater organization was needed to push Nassau forward. 

Leading this endeavor were the two most powerful captains on the island, Hornigold and Jennings, still bitter rivals, but now on more amicable terms. In time, they would each have their own impressive fleets. Hornigold led famous pirates such as Samuel Bellamy, Stede Bonnet and, most notoriously of all, a young Edward Teach — Blackbeard. Jennings’ proteges were just as impressive, with notable names like Charles Vane, “Calico” Jack Rackham, and two ruthless female pirates, Mary Read and Anne Bonny. Together, they founded the Republic of Pirates. And in order to enforce law and order in their new republic, the pirate leaders of Nassau formed what they called The Flying Gang.

Law and order? Pirate republic? It might seem unbelievable, but the pirates were particularly adept in this regard. Because of the nature of their profession and the coordination required to simply survive at sea, pirates had to develop an advanced set of codes. At its core, this was a system of checks and balances. Crews would elect a captain and quartermaster to act as an executive and judicial branch. Captains had absolute power while in battle, but the decision on where to go, what to attack, and how to punish was by vote. Critically, pirate captains had the same food and living conditions as the rest of the men and only received 50% more loot , compared to the 1400% more that a navy captain might receive as a prize. The quartermaster ensured the crew always got their fair share, and, if in doubt, would lead an ousting of the captain. Most impressively of all, any gravely injured pirate would receive payment from a collective fund — insurance. In contrast to the cruelty many were escaping from, this was a breath of fresh, salty air.

Of course, many weren’t aware of their rather progressive governance — and they preferred it that way. The pirates’ greatest weapon was harnessing their perceived barbarity to instill fear in all who opposed their will. Blackbeard would famously hang strings from the brim of his hat that, when lit during battle, surrounded him in smoke — a mad specter, and certainly a terrifying sight for any young navy lad. In making people think that they were capable of anything, pirates had to do nothing. Many would simply surrender at the sight of a pirate ship on the horizon. To encourage this submission, they would often treat their prisoners well and just take what they “needed”, which was frequently rum. Notably, it was also common for members of a captured crew to elect to join their captors. The pirate myths that they actively constructed kept most fearful and far away, but not everyone.

Fall of the Republic

Woodes Rogers was a man of many stories. The son of a wealthy merchant captain, Rogers' life was always intertwined with the sea. In 1707, the waves took him around the world, and upon his return to England he published his Captain’s log to immediate fanfare. Most famously, Rogers stopped at Juan Fernandez Island off the coast of Chile for supplies and found a rather peculiar man — the castaway Alexander Selkirk— the inspiration for Daniel Defoe’s novel, Robinson Crusoe. Rogers became a celebrity overnight, but longed for his next adventure. In 1713, he set out to solidify his legacy as champion of the seas, raising funds to “civilize” the pirate lairs of Madagascar, especially the mythical settlement of Libertalia that had captured the minds of sailors since Avery. Upon arriving, he found that the few mariners on the island had assimilated with the natives, and that they had no access to any vessels of threatening size. Unwavering on his quest of oceanic justice, Rogers set his sights elsewhere — to the rumored pirate den that was forming in the Bahamas.

In the words of the pirate Thomas Barrow, Nassau was a “second Madagascar”, and perhaps even a materialized Libertalia. Leadership under The Flying Gang proved fruitful, and, naturally, Nassau grew in power — and garnered greater attention. It was during this period that Edward Teach, or Blackbeard, would stand out, receiving command of his own vessel and quickly making a name for himself. In short time, he would be elected magistrate of Nassau by his contemporaries and begin working with Hornigold to build naval defenses, notably retrofitting the old hilltop fort to guard the harbor’s entrance. Hearing of this force in the West Indies, King George I of England grew uneasy. The King sought out solutions, and quickly supported Woodes Rogers’ proposal to reclaim the errant colony. Key to this strategy, pardons were offered to anyone who would give up piracy, and Rogers himself would be installed as Governor of Nassau. 

Word spread and pirates realized that they had an important decision to make. To accept the King’s pardon would mean re-integration into society with their plundered wealth in hand. For many who felt content with their treasures, this was a fantastic deal, but others saw the pardon as a siren’s call. A deathblow was struck when Benjamin Hornigold and Henry Jennings, now in their later years, accepted this agreement—the Pirate Republic’s founders surrendering to the might of the British Empire. And what’s more, Hornigold accepted commission as a privateer to hunt down his remaining brethren. Realizing the futility of defending Nassau from the man who built it, The Flying Gang parted ways , and those who resisted succumbed to overwhelming British firepower. Blackbeard fled to the Atlantic Coast where he terrorized for a brief period, but was ultimately hunted down and slain in the shallow waters off the coast of North Carolina. A striking traitor that even Brutus would condemn, Hornigold forsook the republic for empire — and Nassau, the Republic of Pirates, was finished— now in the civilized hands of Woodes Rogers.

A Pirate’s Life for Me

It may be naïve to put forth the notion that these pirates were good people, but one must fairly contend with their ideals. Though ultimately failing in their endeavor, they took on those who had tormented them, defying the British Empire and sparking the democratic sentiment that would later ignite the American Revolution. As global trade sprouted, pirates were indeed the “enemies of all mankind”, or hostis humanis generalis, as it was coined in Admiralty Law. Yet, in their struggle to build their republic on the fringes of the civilized world, they crafted a legacy that would echo into our modern era. The caricatures of peg-legs, eye-patches, and savagery are unimportant; what is truly valuable is their spirit.

And what is that spirit? As Khaldun would note, history is riddled with it. Before casting stones, recognize that the Western world itself stems in large part from barbarians, heretics, and slaves. At a time when Rome was a collapsing authoritarian theocracy, germanic tribes practiced legal freedoms and property rights. Early forms of parliamentary politics were held as moots, or literally a “thing” in old Norse, preceding the early Dutch and British political systems that now dominate the Western world. Once forced to practice in secret, Christianity birthed the modern notion of the individual, catalyzed scientific inquiry, and built a shared system of foundational values. Beyond being the economic backbone for much of America’s history, African Americans captivated many with their arts, in time, forming the rhythm of society and commanding immense social capital. We pretend that we’re the esteemed evolution of Greco-Roman tradition, yet in reality the West is the progeny of outcasts.

Today, the town that sheltered the likes of Avery and Blackbeard is no more. In its place, a monument to our decadence, the Atlantis Resort — a mockery of the utopia they strived to build. It increasingly feels like tentacles are again enveloping the world; new empires that push individuals to the edge. It’s in this moment that a frontier beckons.

Like us, the pirates held a diverse set of goals; among them anarchy, peace, or simply riches befitting a king. Critically, at the center of these ambitions lay a simple truth—one outlined in the mirage of Libertalia. Not all treasure is silver and gold. To be free is to be capable of anything.

The world is certainly much different than it was in the 18th century, and likewise our modern pirates take new forms. Since the mid-20th century, a striking characteristic of the West is the growing self-doubt that we can still accomplish great things. Yet, there remains a brave few. Those who work tirelessly in the fringes of society towards their grand ambition, joined by a crew with strong asabiyyah. Lunatics branded for their barbarism— the enemies of all mankind.

Today’s digital ocean connects us all and technology empowers swift change. Perhaps, in this world, the legend of Satoshi Nakomoto forms a new Henry Avery myth, inspiring a generation of pirates drawn to the pandemic-wrecked treasure fleet of the Federal Reserve. There may also be a Flying Gang of cunning leaders; a dream of the nemesis captains of industry, Jeff Bezos and Elon Musk, someday anchoring ships at remote shores and bringing civilization to the celestial frontier. What might future generations learn from these struggles? Will they be remembered as piratical or visionary? The only certainty is that, without them, civilization enters the doldrums, awaiting a gust of wind to save us from a calm sea. Usurp the status quo, for it is in harnessing our freedom that we unfurl our sails, and in pursuing a better world that we channel the pirate spirit. 

On his journey home to Ithaca, Odysseus is visited by the ghost of Tiberias. The shade advises that, once he passes the trials in his path and returns home, there remains yet one more task. Odysseus is to carry an ordinary oar and walk inland until someone mistakes it for a shovel. It would only be there that he would find peace and his odyssey at an end. I think this to be true of all who brave perilous seas in search of something greater. We must not grow complacent, nor be so foolish to believe that our journey is over. Rather, we must remain steadfast in spite of the challenges before us, and in hopes that one day we might put down the oar for good.

We remember the pirates of Nassau not for who they were, but for who they challenge us to be. Hoist the colors.

-Ryan McEntush