The ocean is a lonely, perilous place. It is especially so when you are aboard a leak-prone wooden vessel laden with a rich cargo of sugar, silks, and opium, like the traders sailing the Quedagh Merchant around India’s southern tip in 1698. They surely panicked when they spied a massive warship with thirty-four mounted guns bearing down on them—or would have, had it not been flying French colors. The Quedagh Merchant had a document, written in an elegant hand, guaranteeing safe passage from France. French ships posed no threat; they might even offer protection, information, or supplies.
The Quedagh Merchant sent over a boat with a French gunner carrying the pass. As he stepped aboard the warship, though, it hoisted a new flag: the English one. The gunner soon realized it was a trap. This wasn’t a French ship; it was Captain William Kidd’s Adventure Galley. And this wasn’t a parley; it was a robbery.
For Captain Kidd, it was a life-changing haul, one that he predicted would “make a great Noise in England.” He was right. Kidd became the “Subject of all Conversation” there, a contemporary wrote, his life “chanted about in Ballads.” One is still sung today: “My name is Captain Kidd, / And God’s laws I did forbid, / And most wickedly I did, / As I sailed.”
It’s as if Kidd and his fellow-marauders never stopped sailing. These days, pirates are everywhere. The five “Pirates of the Caribbean” films have collectively grossed billions. And then there are the shows, games, memes, bars, festivals, and rum bottles. Three major sports teams are named for them—the Pittsburgh Pirates, the Las Vegas Raiders, and the Tampa Bay Buccaneers: the first two from cities with no connection to piracy whatsoever.
The pirates we typically have in mind are specific ones: the English-speaking sea robbers who sailed from the mid-seventeenth century to the first few decades of the eighteenth. And what makes these maritime lawbreakers of long ago so fascinating that, three centuries later, we’re still dressing up like them? The easy answer is that they were rebels. We delight in their lusty, wild lives because we, too, want to live freely. Pirates are especially fascinating because they sailed at the dawn of our era, just as the British Empire was rising and the portcullis of modernity was descending. Viewed in a certain light, pirates—the scourge of admirals and merchants—were the last holdouts against a world dominated by states and corporations.
But were pirates implacable foes of the modern order? Power and piracy were not always clearly distinct, at least not in the early days of English capitalism. It’s worth asking whether the world that pirates mutinied against wasn’t also, in part, a world of their own making.
A sign of our sympathy for pirates is that their heyday is known as the Golden Age of Piracy, roughly from 1650 to 1730. The pirates who lived then can be divided into generations. The first, the buccaneers, plundered Spain’s holdings around the Caribbean in the middle of the seventeenth century. The second, Kidd among them, most often launched from North America’s mainland and secured their greatest bounties in the Indian Ocean in the sixteen-nineties. It was the third generation, sailing from 1716 to 1726, that flew black flags and attacked nearly everyone.
It’s only the last generation, which included notorious captains like Blackbeard and Bartholomew (Black Bart) Roberts, that fully matches our canonical image of the pirate. Interestingly, though, there weren’t many of them. Piracy’s leading historian, Marcus Rediker, estimates that just four thousand pirates sailed in the black-flag era. If he’s right, more people have worked on the “Pirates of the Caribbean” films than were actual pirates of the Caribbean.
If black-flag pirates weren’t especially numerous, they became iconic for good reason. The eighteenth-century pirates were the truly radical ones, Rediker observes, pursuing an existence “as far removed from traditional authority as any men could be in the early eighteenth century.” As he writes in “Villains of All Nations” (2004), “They dared to imagine a different life, and they dared to try to live it.”
Where earlier plunderers, like Kidd, had sailed beneath the banners of leading empires, eighteenth-century pirates often hoisted the Jolly Roger: black (or sometimes red) flags featuring skulls, bones, skeletons, or hourglasses heralding death’s swift approach. These weren’t unusual symbols—they can be found on gravestones of the time—but the skulls on pirate flags were shorn of the customary wings symbolizing the dead’s ascent to Heaven. Removing those wings was a dark, petulant touch from the goths of the high seas.
Much like teen-age goths, eighteenth-century marauders didn’t just stand apart from normal society; they scowled furiously at it. “Damnation to the Governour and Confusion to the Colony,” a typical pirate’s toast went, offered on the gallows. Stede Bonnet named his ship the Revenge, Blackbeard called his the Queen Anne’s Revenge, William Fly went with the Fames’ Revenge, and John Cole offered a double-fudge sundae: the New York Revenge’s Revenge.
This was all a tad theatrical, and no doubt intentionally so: raids went more smoothly when victims were terrified. Still, pirates had real reasons to want payback. The early modern world was unkind to common people, and conditions on merchant and naval ships, where many pirates had begun their careers, were especially appalling. The symbol of a captain’s absolute authority was the cat-o’-nine-tails, though sometimes punishment went beyond flogging to broken arms, gouged eyes, and knocked-out teeth, not to mention death. One sailor reported having been beaten “upon the head with an Elephant’s dry’d Pizle,” which is never good.
Such “hard usage” was rarer aboard a pirate ship. Mutinous, well-armed men did not readily submit to the lash, nor did they accept orders just because an officer had given them. By the rules of Kidd’s ship, the captain needed majority consent to punish men, and important decisions were put to a vote. Historians make much of the “articles” that pirate crews, including Kidd’s, signed. By the eighteenth century, these shipboard constitutions had become astonishingly democratic. Under their terms, generally, captains were elected, the injured received recompense, and pay came in shares rather than in wages, with captains rarely getting more than twice what ordinary seamen did. (The average ratio of C.E.O. pay to median worker pay at the largest U.S. firms today exceeds two hundred to one.)
Examples of pirates’ articles appeared in “A General History of the Pyrates,” a 1724 book that is the source of much pirate lore. (For decades, it was attributed to Daniel Defoe.) A second volume further explored pirates’ unorthodox politics. It described a short-lived settlement in Madagascar, named Libertalia, in which pirates shed their national allegiances to become Liberi, the people of freedom. They formed a democracy, pooled their treasure, freed the enslaved people they encountered, and eschewed money as “of no Use where every Thing was in common.”
Libertalia, we now know, was a fiction. Still, the U.S. anarchist Hakim Bey latched on to it, a few decades ago, insisting that it epitomized the piratical spirit. For Bey, “pirate utopias” were “temporary autonomous zones” offering refuge from an inhospitable world. His ideas informed the recent pro-Gaza student encampments, which were, for some, little Libertalias on the quad.
Did pirate utopias influence politics at the time? The late anthropologist David Graeber suggests as much in “Pirate Enlightenment, or the Real Libertalia” (2023). The Libertalia of “A General History” never existed, Graeber acknowledges, but pirates did come ashore in Madagascar, and their children, with Malagasy women, founded politically interesting societies there. Moreover, reports of pirates’ radical social experiments “made a profound impact on the European imagination,” Graeber writes. It is perhaps not coincidental that eighteenth-century philosophers were publishing thought experiments about how free individuals might hypothetically make social contracts at just the time when pirates—in full view and not hypothetically—were doing precisely that.
In “A General History,” Libertalia’s leader is said to have “abhorr’d even the Name of Slavery.” This was an enlightened view, given that the original European utopia, Thomas More’s, from 1516, had promised two slaves per household. Whether actual pirates opposed slavery, however, was a more complicated question. Certainly, they trafficked and owned people. According to the articles of Kidd’s ship, any crew member who lost a limb would receive cash or “six able Slaves” in compensation. Yet some pirates were Black, especially by the eighteenth century, when the pirate ship became the site of what Rediker calls a “multicultural, multiracial, and multinational social order.” In all, the enslaved probably faced better odds among pirates than they did elsewhere in the white-run world.
Did women also find freedom at sea? “A General History” tells of one, Anne Bonny, who left her husband to join “Calico” Jack Rackham’s crew, dressing as a man and fighting as a pirate. Aboard, Bonny took a “particular Liking” to a “handsome young Fellow” and revealed her secret to him. Her handsome crewmate replied, awkwardly, that he was also a woman in disguise; her name was Mary Read. Their meet-cute story in “A General History” is hard to swallow, but there’s ample documentation that Bonny and Read did wear britches and sail with Calico Jack. And, although we know of only a handful of women who left domestic drudgery for the pirate’s life, the historian Jo Stanley conjectures that “many more” were lost to history.
The most tantalizing speculative line concerns pirate sexuality. Although pirates were long represented as superabundantly straight Errol Flynn types, the historian B. R. Burg made national news in the nineteen-seventies by proposing that homosexuality was widespread among pirates. Could one really expect the rowdy men who chose to live within a transgressive, all-male milieu to forgo sex? Surely not, Burg argued. They created a “functioning and resilient sodomitical pirate society,” he wrote—a floating community where men could love freely.
Popular culture has come around to Burg’s thesis. In the 1991 film “Hook,” Dustin Hoffman and Bob Hoskins quietly played Captain Hook and Smee as what Hoffman called “a couple of old queens.” Johnny Depp has said that he played Jack Sparrow as gay in the “Pirates of the Caribbean” films (2003-17). This trend culminated in the rainbow-splashed HBO Max show “Our Flag Means Death” (2022-23), in which Blackbeard and Stede Bonnet are boyfriends.
The trope of the gay pirate nicely encapsulates the broader understanding of the pirate ship as a nautical autarky, with no ties to land, not even sexual ones. The buried-treasure myth fills out that picture. The idea is that, rather than spending their loot, pirates hid it in secret places they shared only with one another, through whispered confidences and cryptic maps. We imagine pirates as inhabiting sealed-off worlds, with the ships their homes, their crewmates their families, and remote islands their banks. All the rest can go hang.
But had pirates truly seceded from land? It’s hard to prove that they had sex with one another at sea. The evidence is “so sparse as to be almost nonexistent,” a scholar following in Burg’s footsteps conceded. There’s also no evidence that pirates hoarded their treasure in buried chests. What there is evidence for—lots of it—is pirates spending their loot on women ashore. Pirate ships may have been oases of freedom, but they were also cramped vessels where rations ran low and tensions ran high. When they reached shore, the men shot out like cannonballs, aiming for the taverns and brothels. Coins flew in all directions. One buccaneer gave a woman five hundred pieces of eight—an eye-watering sum—to see her naked.
This is a different side of pirates: not nautical rebels but eager participants in portside economies. This role is emphasized in two important books from 2015, Mark G. Hanna’s “Pirate Nests and the Rise of the British Empire, 1570-1740” and Kevin P. McDonald’s “Pirates, Merchants, Settlers, and Slaves.” Both are academic monographs with little patience for swashbuckling. Instead, they treat pirates as being tightly enmeshed in the societies surrounding them.
To appreciate pirates’ place within early modern life, it helps to zoom out from the ferocious “black flag” moment of 1716-26 and consider the larger context. Spain and Portugal had seized valuable colonies in the West, and India and China had amassed great riches in the East. England, however, was largely locked out. It neither ruled the waves nor commanded a vast empire—not yet, anyway. London thus welcomed anyone who could crack open the treasure stores to the east and west. And it did not flinch when the men who stepped forward were pirates.
Piracy is, after all, a subjective matter. Was it a crime to take to the seas and plunder ships, attack towns, torture people, and seize a fortune in silver from Spain’s American colonies? For the Spanish, it absolutely was, and they called the villain responsible El Draque (the Dragon). But when El Draque’s ship returned to Plymouth and deposited five tons of stolen silver in the Tower of London—more than the Crown took in from all other sources combined that year—Queen Elizabeth was willing to forgive the sin, board the ship, and knight its captain. The English know El Draque as Sir Francis Drake, and remember him not as a pirate but as a bold explorer.
“Other than that, they’re super low-maintenance.”
Cartoon by Ellie Black
They saw Captain Kidd similarly, at first. Kidd had been a respected member of New York society, with a house at 56 Wall Street and a pew at the nearby Trinity Church. The reason he had such a large warship is that he had the financial backing of some of England’s most powerful men. When the Adventure Galley set sail from Manhattan, it did so to a flourish of trumpets.
Captains like Kidd weren’t naval officers acting under direct orders, but they had broad license to rob England’s rivals. That license, ideally, took the form of permission slips, called letters of marque or reprisal, which deputized them to attack certain foreign ships for a cut of the loot. Possessing such letters technically made them “privateers” rather than pirates. This is how Kidd saw himself as he carried a royal commission to seize French ships (and another to attack pirates). Admittedly, it required squinting to see his main prize—the Indian-owned, English-helmed Quedagh Merchant—as French. But this was a great age for squinting. Privateers often relied on letters that were invalid, expired, or issued after the fact, when they had letters at all.
For the most part, the authorities didn’t mind. So long as the pirates had their prows pointed in the right direction, their work was good for business. Not only did they harry England’s rivals; they also enriched its colonies. McDonald notes their importance in furnishing new settlements with enslaved people, who were initially hard for English colonists to buy through normal trade. The Africans sold into bondage in Virginia in 1619 (the event that prompted the New York Times’ 1619 Project, four centuries later) had been seized from a Portuguese slave ship by an English privateer carrying a Dutch letter of marque.
Pirates also supplied cash. The Americas produced prodigious amounts of silver and gold, but the mines were in the Spanish and Portuguese colonies. The English colonies, meanwhile, suffered chronic shortages of the metal they needed to pay England’s taxes and buy its goods. One turn-of-the-eighteenth-century observer estimated that the average coin lasted only six months in America before leaving for England. Since imperial rules and rivalries blocked English colonists from trading directly with their Spanish and Portuguese counterparts, pirates and smugglers (two overlapping categories) were indispensable. They tapped the rich vein of minerals flowing from the Americas to Iberia, irrigating the English empire with hard currency.
“Pieces of eight” and “doubloons” sound like colorful pirate talk, but they were the English names for Spanish coins, which the pirates stole in their raids, earned from their trade, and spent on their sprees. These, plus gold coins from Indian Ocean plunder, flooded colonial societies. The familiar dollar sign, in fact, was originally the American symbol for the peso, the fabled “piece of eight.” In cash-parched America, illicitly acquired Spanish silver was the predominant currency, so it became the sign for money.
Pirate sexuality is relevant here, because sex was a crucial conduit through which foreign coin entered the colonies. The ports that pirates favored were hotbeds of prostitution. This was illegal, and in the pirate haunt of Port Royal, in Jamaica, “common strumpetts” were jailed in a “cage by the turtle market,” a visitor wrote. But, rather than locking these women in the wench kennel, Jamaica should have erected statues to them for resolving the colonial liquidity crisis. The largest statue should be of the unnamed woman who talked a pirate into giving her five hundred pieces of eight just to watch her strip. Forget Blackbeard; she’s the outlaw they should be making television shows about.
The ports also brimmed with silversmiths. We think of silversmithing as a classic “ye olde” profession; Paul Revere was a silversmith, and, generally, they outnumbered lawyers in Colonial America. But why were any there at all, given that the land had little by way of silver mines? The answer, Mark Hanna explains, is that silversmiths worked as fences, transmuting “pirate metal” into respectable wealth. The first mint in the thirteen colonies was established in 1652 by John Hull, who made Massachusetts pine-tree shillings from Spanish bullion. Hull was a silversmith; his brother Edward was a pirate.
John Hull faced charges for backing his brother’s pirate ship, but he was acquitted. Such outcomes were common, Hanna and McDonald observe. Although piracy was a felony, it could also be a bonanza, and sympathetic locals made prosecution difficult. Hanna gives the example of one Moses Butterworth, who had sailed with Kidd. When Butterworth was tried for piracy in what’s now New Jersey, an armed militia stormed the courthouse. The judge drew his sword, but he was no match for more than a hundred men with guns and clubs. They freed Butterworth and seized the governor and the sheriff, taking them prisoner. They then held the governor for four days, by which point Butterworth was long gone. (He turned up three years later in Newport, Rhode Island, captaining his own vessel.)
Richard Blakemore’s new book, “Enemies of All,” addresses this theme. In Pennsylvania, Blakemore notes, a prominent pirate married the governor’s daughter and was elected to the legislature. An even more prominent pirate, Henry Morgan—known to spiced-rum aficionados as Captain Morgan—was arrested and hauled to London. Then, after being released without punishment, he was knighted and returned to Jamaica, where he served several stints as the acting governor. When Morgan died, in 1688, he received a state funeral in Port Royal, with a twenty-two-gun salute. Pirates were reportedly given amnesty to join the mourners.
Like Morgan, Kidd faced the possibility of prison. But, even with a warrant out for his arrest, he came ashore to discuss his case with the Massachusetts Council. It helped that Lord Bellomont, then the governor of New York, Massachusetts Bay, and New Hampshire, had been one of Kidd’s chief financial backers. Kidd sent Lady Bellomont an enamelled box containing four diamonds set in gold. He explained to the council that his acts, though technically unlawful, were justifiable. Kidd could be forgiven for expecting mercy. And he could be forgiven his surprise when Lord Bellomont, his former investor, had him arrested.
William Kidd grew up at a time when pirates were imperialist Robin Hoods, robbing foreigners and giving to the English. This made them affable outlaws, more raffish than villainous. The trouble arose at the century’s end, when pirates’ depredations interfered with London’s growing maritime dominion. It was Kidd’s misfortune to sail at a “turning point in the history of empire,” his biographer Robert C. Ritchie writes. He had set out in a permissive era, and he returned in a punitive one.
It helps to think of piracy as a phase in early modern venture capitalism. That’s the argument persuasively made by the economic historian Nuala Zahedieh, who studies the English Caribbean. Sugar planters there envisaged large profits but had to make serious investments—buying enslaved people, clearing land, building roads and harbors—before realizing them. Backers in London were understandably wary. The most “hopeful” economic foundation for Jamaica, one of its governors believed, was thus raiding. It was an “ideal start-up trade,” Zahedieh agrees, in that it required only a small initial outlay—especially small because pirates worked for shares rather than for wages. Piracy was dangerous, but it generated the quick cash needed to launch plantations. Theft on the seas thus helped to establish more reliable forms of plunder: of Native land and African labor.
But, as plantations took root, piracy lost ground. The two endeavors were “absolutely incompatible,” a less sympathetic governor of Jamaica wrote, since one required order and the other stirred chaos. Slaveholding planters sought social control on land and safe passage on the seas—and pirates imperilled both. If, in the seventeenth century, pirates had been instruments of English colonization, by the eighteenth they were obstacles to it.
London also found that pirates interfered with the East India Company, the chartered trading firm that would become the bridge to Britain’s conquest of India. This was Kidd’s great crime. His theft of the Quedagh Merchant, which had been transporting goods owned by a high-ranking Mughal official, provoked fury on the subcontinent. The Mughal emperor insisted that, if the English wanted to continue operating there, justice must be served. Lord Bellomont’s arrest of Kidd, in 1699, was a sacrifice made on the altar of English trade.
By then, the Crown had grown hostile to piracy. Its pirate hunt was paused during the War of the Spanish Succession (1701-14), which required hustling anyone at hand onto English ships to fight. But, after that war ended, the final confrontation began. Demobilization cut more than forty thousand men loose from naval service, and privateering dried up, too. Some of the unemployed predictably took to piracy, but, as they did, they faced tighter naval control, growing legitimate trade, and a punitive turn in the colonies. Men who once could have leaped ashore and married the governor’s daughter now risked arrest, conviction, and execution.
Henry Morgan, in the late seventeenth century, had retired from piracy and invested in slaveholding and plantations. The pirates of the eighteenth century lacked such easy off-ramps. They were sea-locked, with the ports plugged up against them. That’s when they raised the black flag and fought the whole world. But another way to put it is that the whole world fought them.
According to Marcus Rediker, this brought pirate radicalism into full bloom. As merchants withdrew from piracy, it became more proletarian. Its levelling, libertarian tendencies were clearest after 1716, when seafaring men seized their workplaces—the ships—and founded their own societies. Theirs was a “world turned upside down,” Rediker writes, a happy fraternity in which no one would hit anyone else with an Elephant’s dry’d Pizle. Small wonder that the powers that be refused to rest until every pirate was reformed, jailed, hanged, or drowned.
Not all historians regard black-flag pirates as political visionaries, though. Take their wealth-sharing plans. Are they evidence of socialism? Zahedieh notes that payment by shares can also be understood as a way of reducing labor costs by, essentially, replacing wages with lottery tickets. If pirates got lucky, they’d flourish, but if not they’d starve: “No prey, no pay,” as they said. Kidd’s generation of pirates had also worked for shares, but they’d had prey clearly in view—hence Kidd’s rich investors. Later pirates lacked “a clear objective,” Blakemore writes, and were “more directionless.”
Kidd’s seizure of the Quedagh Merchant was among the last legendary hauls. With huge scores now rare and the gallows looming, eighteenth-century pirate ships grew less desirable as places to work, and they relied more on coercion to replenish their ranks. One reason for their multiracialism was that they struggled to recruit white men. The motley crews that today look so admirable may have been products less of democracy than of desperation.
From Madagascar, site of the fictional Libertalia, we have an account of profit sharing in a real pirate settlement. Fourteen men in straitened circumstances agreed to combine their meagre fortunes, divide into teams, and fight to the death for the pot. The two survivors shared the winnings. This was a bold social experiment, but not one undertaken by free men who believed another world to be possible. It was, rather, a last-ditch scheme—the hopeless radicalism of the wretched.
The Crown’s crackdown meant that William Kidd faced a jury in London, not one in pirate-coddling New England. “I am the innocentest person of them all,” Kidd protested. He made much of the French pass that the Quedagh Merchant had carried, which in his view made it fair game. This defense might have worked a generation ago. But now? Kidd’s acts had been “the most mischievous and prejudicial to trade that can happen,” the judge told the jury. Kidd was convicted and sent to Execution Dock in Wapping.
Kidd, and everyone else. Rediker estimates that from 1719 to 1725 the number of pirates fell from about two thousand to fewer than two hundred. Hundreds of pirates swung on hundreds of nooses, their feet dancing madly in the air. The corpses of especially notorious pirates were then put on gruesome display. Kidd’s was suspended by chains, for years, over the Thames.
The end of British piracy was, oddly, the start of Britain’s pirate obsession. There was a hit play in 1713, “The Successful Pyrate.” In 1719, Daniel Defoe published “Robinson Crusoe,” seemingly based on the travails of a famed buccaneer who’d been marooned. (Defoe wrote a proper pirate novel in 1720.) In 1724, the much read “General History” set the terms for how we still discuss piracy. Just as pirates were dying out, they were becoming immortal.
One could see this as nostalgia, with pirates standing for a bygone era. But was their way of life truly lost? The twilight of the pirates was the dawn of the slave trade, American plantations, and Britain’s global empire. Plunder wasn’t being forsaken so much as redirected and made routine. Perhaps seeing the world as pirates did, with theft as adventure and stolen goods as booty, helped to soothe British consciences. In life, the pirate had been spurned as an impediment. In death, he served—cutlass aloft, eye patch affixed—as a roguish mascot for a predatory age. ♦