Golden Age Pirates — A Lifestyle
Throughout history, embroidered with tales of valor and villainy, the narrative of the Sea Rovers — the Pirates — has been crafted by individuals as diverse as the seas they roamed. The chronicles of Piracy reveal a motley parade of characters, each drawn into the Piratical fold by a confluence of fate, fortune, and ferocity.
Consider, if you will, the epoch of the 1500s, where in some secluded corners of the world, the cradle of Piracy rocked gently, nurturing infants in the art of maritime larceny. Among such notorious progeny was Grace O’Malley, the Pirate Queen of Ireland. Grace, inheriting her father’s stirring fleet, was a scion of the sea, her childhood laced with the salt of the ocean and the lore of the looters. In her veins coursed the legacy of familial Piracy, a tradition saturated in the plunder of neighboring shores and foreign lands.
Yet, as the tides of time surged, the familial fabric of Piracy began to fray. The advent of burgeoning corporations and their leviathan-like ships ushered in a new era, where the audacious assaults on these monolithic entities supplanted the wanton raiding of clans and kingdoms. Such brazen acts, once lauded, now beckoned the hammer of legal retribution.
And in the golden age of Piracy’s dawn, there lay a cadre of naval men, erstwhile servants of their sovereign seas, now cast adrift by the ebbing fortunes of war. Men like Ben Hornigold, a captain whose allegiance to the crown was as steadfast as his command of his ship. Yet, when the drumbeats of war faded, Hornigold’s deeds, once draped in the banner of patriotism, were now cloaked in criminality. A pedagogue of Piracy, Hornigold’s legacy included the tutelage of the fearsome Blackbeard, his acumen in nautical knavery seeding a lineage of well over 1,500 Pirates. Among these Corsairs were those fueled by vengeance, like Jeanne de Clisson, the Lioness of Brittany. Betrayed by a monarch’s whim, she transformed her grief into a grim crusade, her black-hulled ships becoming harbingers of doom for the nobility of France. Unlike her male counterparts, Jeanne, cloaked in her noble birthright, eventually retired from her marauding ways, a luxury seldom afforded to those of lesser birth.
The underbelly of maritime life often writhed with discontent. Sailors, beleaguered by the harshness of their captains and the brutality of their existence, sometimes found their salvation in mutiny, their pent-up fury and despair propelling them toward the Piratical path. Others were lured by the siren call of Piracy, enticed by promises of riches, freedom, and retribution against their oppressors.
Nevertheless, the path to Piracy was not solely paved with coercion or desperation. There were those like Stede Bonnet, born to privilege, who sought the buccaneer’s life as an escape from domestic drudgery. Or Mary Reed, donning the guise of a man, who found in Piracy a liberation from societal shackles. And then there were the enslaved, who, upon their emancipation by Pirate hands, joined the ranks of their liberators, though their names rarely graced the records of fame. Moreover, the narrative of Piracy is replete with such characters as John King, a mere boy who, driven by unknown motives, chose the risky path of Piracy over the comfort of home. It speaks of an era where the call of the sea was a clarion to the restless, the wronged, the adventurous, and the audacious.
Thus, in the multifaceted saga of Piracy, one discerns that the reasons and means to join this shadowy fraternity were as diverse as the turbulent waters they sailed. The Pirate’s life, a maelstrom of danger, freedom, and infamy, was a choice made by many, each for their own reasons, each leaving a fixed mark on the vast, unfathomable ocean of history.
Culturewise, the mantra “A short life, yet a merry one,” is reiterated in the hearts of those valiant souls. These marauders, weary of the toil and drudgery under tyrannical captains for meager wages, swore a new creed of defiance. “Enough!” they proclaimed, their spirits aflame with indignant fury. “No longer shall we endure this oppression!” And with that fiery resolve, they set upon a path of exhilarating liberation.
These brigands, often depicted in chronicles as leading lives mired in misery and savagery, indeed faced harsh realities. The life of a sailor in that age was a fleeting candle, snuffed out by maladies, the harshness of the sea, or the wrath of combat. Their sustenance was meager, often tainted with the bitterness of disease, and their bodies bore the scars of arduous labors and the excesses of spirits. Yet, amidst the turmoil and skirmishes on the high seas and in the lawless taverns ashore, one might wonder, could joy be found in such existence?
The answer lies in the comparative liberty they enjoyed. While their lifespans mirrored those of their seafaring brethren, Pirates sailed across the treacherous waters of fate with a semblance of autonomy. Unlike their counterparts on merchant or naval vessels, plagued by diseases in squalid ports or aboard decaying ships, Pirates wielded the power to abandon such wretched vessels and chart their own course.
Furthermore, in the microcosm of their floating realms, these outlaws dined as equals, from the loftiest captain to the humblest deckhand. A democratic brotherhood formed, united in their status as outcasts, elevating their collective standing above that of the lawful yet downtrodden sailor. And though their fare was simple — salted meats, hardtack, and dried legumes, repugnant to the modern palate — it was, by the standards of the day, a feast fit for kings, for it was chosen by those who partook in it.
And amidst the intense waves of the Age of Sail, Pirates stood as defiant emblems of leisure in a world that scarcely knew the concept. To comprehend this blunt contrast, one must delve into the ethos of the Protestant work ethic, a paradigm profoundly sculpted by Max Weber’s insights in 1905. This ethic, deeply rooted in Protestant, particularly Calvinist, values, championed diligence, discipline, and austerity as cardinal virtues. It was this ethos that fueled the ascent of capitalism, transforming even the most mundane of labors into a Divine vocation, a calling from the heavens to be pursued with unwavering zeal.
Tracing its origins to Martin Luther, this ethic reframed earthly toil as a duty that enriched both the individual and the community. While Catholicism extolled good works as a tangible expression of faith, Calvinist doctrine, enfolding “sola gratia,” posited that salvation, preordained by the Divine, lay beyond the grasp of mere labor. This perspective redefined the Protestant view of work as a stewardship, a conduit to bless others rather than a path to salvation. Hence, industriousness and thrift were not merely lauded but deemed indispensable manifestations of one’s Divine stewardship.
In this backdrop, Pirates emerged as mavericks, indulging in extravagant respites, an absolute antithesis to the prevailing ethos. These buccaneers, after brief bouts of plundering, adopted a life of ease and leisure, pursuing the very joys they believed to be the essence of a blissful existence. Historical reports suggest they achieved this with resounding success.
The Piratical lifestyle also addressed a quandary familiar to modernity: the human inclination to gravitate toward a baseline level of contentment, a personal norm of happiness. Pirates countered this natural equilibrium by engaging in acts of intimidation and violence against their societal superiors, those who once scorned them. They reveled in an abundance of spirits, the very embodiment of their desires, and in such variety that it offered a continuous thrill.
These Corsairs also entertained the possibility of adventures to distant lands — from the Pirate havens of Madagascar, New York, and Boston, to the plunder-rich Spanish settlements in Central and South America. Most crucially, they harbored dreams. In an era where social mobility was a distant fantasy for the common folk, a Pirate could envisage a meteoric rise to the pinnacle of society, even to the halls of Parliament. Accordingly, Bartholomew Roberts encapsulated this ethos in his proclamation:
“In an honest service there is thin commons, low wages, and hard labor; in this, plenty and satiety, pleasure and ease, liberty and power; and who would not balance creditor on this side, when all the hazard that is run for it, at worst, is only a sour look or two at choking. No, a merry life and a short one, shall be my motto.”
In these words lies the essence of the Pirate’s creed — a bold renunciation of the stringent Protestant ethic, in pursuit of a life filled with freedom, power, and fleeting joy.
Thus, within the hullabaloo of their lawless lives, the Pirates found a semblance of egalitarianism, a taste of freedom not afforded to those who walked the straight and narrow. In their world, where every man’s voice held weight and each shared equally in the spoils and spoils, there was a certain nobility, a fierce joy that perhaps made their brutal, fleeting existence, under the unforgiving sun and amidst the relentless sea, a life worth the living.
Appearance
In the halcyon days of the Golden Age of Piracy, there existed a prevailing belief, festooned in the accounts of maritime lore, that Pirates garbed themselves in garish and flamboyant attire. This notion, while partially steeped in the fantastical imaginings of Robert Louis Stevenson’s 1883 literary masterpiece, Treasure Island, held but a grain of truth. Pirates, in their core essence, were seasoned mariners, and their sartorial choices reflected the practical necessities of a life surrendered to the unpredictable whims of the sea. Yet, it is an incontrovertible truth that certain buccaneers, particularly those of the captain’s rank — as we divulged earlier, did indeed indulge in a wardrobe designed to inspire astonishment and assert their hard-won status.
Fashion Background
Before we dive into the notable Pirate attire, it is worth exploring a background on how we came to acknowledge what New World Pirates actually wore. The true visage of Pirates remains covered in mystery, for the lack of pictorial evidence leaves much to the imagination. In an era bereft of photographic technology, those gifted with the artistry to render lifelike depictions seldom found themselves in the company of Pirates. And even if such rare talents did cross paths with these outlaws of the sea (as many sailors were known to possess artistic prowess), their works have tragically vanished into the mists of time.
Art of the period was largely the purview of the affluent and influential, who commissioned resplendent portraits of themselves and their associates, or idyllic landscapes. The
world of Pirates, along with the impoverished, the oppressed, and the vagabonds who often swelled their ranks, was not a subject deemed worthy of artistic immortalization.
Yet, there was one man, William Hogarth, whose engravings offer a glimpse into the potential early life of a Pirate. Hogarth, emerging from humble beginnings in the lower echelons of the middle class, found his calling as an apprentice to an engraver in his adolescence. This flourishing art form, engraving, found favor among London’s less opulent citizens, serving as a precursor to modern methods of art reproduction.
Engraving involved punctiliously etching an image onto a metal plate. Ink, when applied to the plate, clung to the etched lines but was repelled by the smooth metal, allowing for the creation of multiple detailed and subtle prints. This technique marked a significant advancement from the more rudimentary woodcarving methods of the past (e.g., Plate 5 below — The Idle ‘Prentice turn’d away, and sent to Sea.)
In his early career, Hogarth specialized in producing the progenitors of modern business cards. Commissioned by shopkeepers, these cards featured illustrations emblematic of their trade — a sheep for a wool merchant, cupids for a perfumier, and so on. These cards rapidly gained popularity, evolving into what would later be known as Trading Cards, and in doing so, they fostered a new artistic genre.
Hogarth’s mastery of his craft was such that by the age of 23, he was a self-employed engraver, and at 27, he ventured into painting. Despite initial skepticism from a client who doubted his painting skills, Hogarth triumphed, vindicating his artistic versatility through legal means to secure the remuneration stipulated in his contract. Following his initial success, William Hogarth expanded his repertoire, venturing into the creation of large engravings designed for framing, his works imbued with a satirical edge — a melding of humor and poignant social commentary. One of his earliest endeavors in this vein was a comedic take on the infamous South Sea Bubble, a notorious scheme reminiscent of a pyramid ploy, which led to the financial ruin of many Londoners while others blindly pursued its deceptive promise.
Hogarth’s artistic journey continued to flourish as he produced an array of works. While some of his creations catered to the portraiture of the affluent, he increasingly found inspiration in the raw and unvarnished life of London — its inebriates, courtesans, lunatics, and destitute youth. One notable piece, The Enraged Musician, encapsulates urban life. The scene depicts a violinist of means, engulfed in the discordancy of the streets — the cries of a milkmaid, the blare of a coachman’s horn, the whirr of a knife sharpener’s grindstone, and the melancholic song of an impoverished mother. These very sounds might have echoed in the ears of a young Sam Bellamy.
In his engravings, Hogarth unflinchingly portrayed the grim reality faced by the impoverished in 18th-century England. The Distressed Poet illustrates the plight of a writer hemmed in by penury and debt in a sparse attic. And in the moving six-part narrative of The Harlot’s Progress, Hogarth traces the harrowing descent of a young woman into prostitution, her spiral into indigence, and her eventual demise, with one scene notably featuring an outlaw’s portrait in her humble abode. Then there was The Industry and Idleness, a series that juxtaposes the destinies of two young men: one who embraces conformity and climbs the social ladder, and Tom Idle, who rejects the monotony of apprenticeship for a path fraught with misadventure. Tom’s choice to become a sailor mirrors the era’s disdain for seamen, and his escapades in brothels and raucous taverns subtly suggest a pivot toward Piracy, underscored by the presence of purloined watches.
In contrast, the industrious apprentice’s trajectory, particularly following his marriage into his employer’s family, captures the societal chasm. In one scene, the newly affluent apprentice dispenses alms to the destitute, while a servant offers leftovers to a thankful woman in poverty.
Moreover, Hogarth’s dual works Beer Street and Gin Lane offer an absolute dichotomy of English lower-class life. Gin Lane portrays the dire consequences of rampant gin consumption — the desperation of pawning belongings for liquor, the specter of starvation, and the decay of society. In contrast, Beer Street paints a rosier picture of the working class, indulging in beer but maintaining a semblance of health and well-being, with notable depictions of public affection and the shabby appearance of an artist advertising gin.
Thus, collectively, these works of Hogarth present a profound and incisive commentary on the societal issues, poverty, and the perils of vice that permeated 18th-century England. And through these works, we catch a fleeting glimpse into the streets and lives that may have once been the breeding ground for those who would take to the seas under the black flag of Piracy. His work stands as a rare window into a world that, in other respects, remains veiled in the shadows of the past.
The Fashion
The fabric of a Pirate’s daily life was woven from practicality. Linens and wools, sturdy and durable, were the sinews of their seafaring attire. From the looms of the age emerged textiles such as broadcloth, celebrated for its rich hues and finish; kersey, a safeguard against the biting cold; shag, akin to a rustic velvet; and the Welsh plains, a cousin to flannel. The term “cotton” in this epoch referred not to the cotton of modern parlance, but to a woolen fabric, its surface resembling the softness of the plant’s bloom. True cotton remained a luxury, a rare import from distant shores. Meanwhile, fustian, a blend of cotton and linen, provided a more accessible option for the less affluent.
The palette of the Pirate wardrobe was predominantly subdued — shades of blue, tan, dark green, white, and grey — reflecting the somber realities of maritime life. Yet, the monotony was occasionally punctuated by the vibrancy of scarlet or the cheerfulness of yellow, introduced through silk scarves and sashes, a subtle nod to a Pirate’s penchant for theatrics.
Amidst these sea-hardened men, the Pirate captain stood as a figure of sartorial distinction. His coat, often a trophy appropriated from a wealthy captive or acquired ashore, spoke of his elevated status and the greater share of plunder he commanded. Fashion in those times dictated that coats be adorned with a plethora of buttons and expansive cuffs, a style not lost on the Pirate elite. As mentioned before, Bartholomew Roberts, with a fame that spanned the seas, was particularly renowned for his scarlet silk coat and damask waistcoat, earning him the moniker “le jolie rouge” by the French, his most hated adversaries. His success was also reflected in the opulent display of a gold necklace, its cross gleaming with diamonds.
Roberts’ concern for appearance extended beyond his own; he ensured his crew were never seen in rags. His ship’s articles, a contract binding each man to his command, guaranteed a fresh “shift of cloaths” from each captured vessel. This gesture was as much an act of vanity as it was a reflection of the pride and unity of his fearsome crew, a band of brothers bound by the sea and their shared fortune.
The attire of the common seaman showcased both functionality and resilience. Their garments were tailored to the demands of a life in constant motion, amidst the ropes and sails of their floating dominion. The shorter jackets of the ordinary seamen, known colloquially as “fearnoughts,” were a staple of nautical garb. Forged from heavy blue or grey cloth, these jackets were designed for warmth and utility, their lack of tails a practical concession to the agile dance required amidst the ship’s rigging. The name “fearnought” itself was a nod to the bravery of those who climbed the towering masts in tempestuous weather, a prelude to the later “reefer jacket” moniker. These jackets, wrought from either wool or durable fustian, were the silent allies of those who braved the heights and depths of the sea.
In contrast, the Pirate “officers” — the quartermaster, boatswain, and their ilk — donned slightly longer jackets, which grazed the mid-thigh, a subtle marker of their elevated status within the ship’s hierarchy. The buttons that enhanced these garments, whether on coats or other forms of clothing, were crafted from an array of materials: brass, tin, bone, horn, or fabric-covered disks, each telling its own story of origin and craftsmanship.
When the wrath of the sea unleashed its fury, a longer, more waterproof canvas coat became the mariner’s bulwark against the elements. The neck scarf, versatile in its use, served as both a shield against the biting wind and a tool to absorb the sweat of labor under the harsh Caribbean sun. Beneath their coats, the sailors donned linen shirts, collarless and utilitarian, pulled over the head in the simplicity of design born of necessity. Waistcoats, both sleeved and sleeveless, added an extra layer of warmth and style, their patterns varying from solid colors to stripes and chequers.
The seafaring trousers, known for their baggy, bell-bottomed design, were a hallmark of the mariner’s attire. Crafted from materials like serge, these trousers were practical for a multitude of tasks — from swabbing the deck to scaling the rigging, or wading ashore. Infamous female Pirates, Anne Bonny and Mary Read, donned these very trousers and shirts, blurring the lines of gender in their fierce battles. For added functionality, leather pockets were often affixed to these trousers, and in colder climes, woolen stockings of varying lengths provided much-needed warmth.
Contrary to popular portrayal, the tricorne hat was not a staple of the Pirate captain’s wardrobe. The large brim, while fashionable on land, proved a hindrance on the deck of a ship in constant battle with the wind and waves. Notable exceptions like Captain Kidd and Stede Bonnet may have sported such headgear, but for most, it was impractical. Bartholomew Roberts’ feathered hat and Blackbeard’s infamous lit fuses under his hat during battle stood out as unique sartorial choices, each reflecting the individuality and bravado of these legendary figures of the sea.
But historically speaking, from the early 1600s, the masculine silhouette was crowned by a hat crafted from sturdy felt, its wide brim a halo framing the visage of the wearer. These hats, though consistent in their basic anatomy, varied in the shape of their crowns — some round as the full moon, others flat as the tranquil sea.
A sartorial schism emerged in England during the turbulent years of the Puritans and the English Civil War, a time when fashion spread out as the banner of one’s allegiance. The contradiction was stark: the Puritans, adherents of austerities, donned hats as unembellished as their creed, earning them the moniker “roundheads” for their simple crowns. On the other hand, the Royalists, loyal to the crown and its riches, festooned their hats with extravagant plumes and turned-up brims — a silent defiance against the asceticism of their rivals.
As the century waned, a new style emerged amongst the fashionable: the tricorn, a hat with brims turned up in three places, forging a trinity of points. This style, synonymous with the swashbuckling image of Pirates, was in truth the vogue of the era, a sartorial choice not monopolized by seafarers but rather a ubiquitous trend.
The tricorn’s genesis lay in the military conflicts between France and Spain in the 1650s, soon becoming the height of fashion in France. Across Europe, variations flourished: the English favored simplicity with a mere hint of color along the brim, while Italians garnished theirs with metallic trims, and the French added a flourish of feathers.
And in the theatrics of Piracy, where each captain was both a marauder of the seas and a maestro of his own legend, the wearing of wigs was a symbol of affluence and respectability. Mirroring the fashion of the 17th and 18th-century gentry, these wigs were not purely ornamental but a barometer of one’s perceived wealth. The length and volume of the wig, a cascading mane of artificial hair, became synonymous with status, hence the enduring phrase “big wig”. A Pirate captain, with a penchant for the grandiose, might embellish his wig — be it entirely white or raven black — with ribbons of vibrant colors, a visual spectacle of his flamboyant persona.
Blackbeard, however, eschewed the wig. Instead, he chose to weave black ribbons into his formidable black beard, a choice that only amplified his fearsome reputation.
Now, the image of a Pirate with a colorful bandana is a fixture in the collective imagination, fueled by countless illustrations and cinematic portrayals. However, historical veracity casts doubt on this sartorial choice. The term “bandana,” rooted in the Hindi word bandhnu, refers to a dyeing technique rather than a specific item of clothing. It was more common for ordinary seamen to don a simple headscarf, tied at the front, leaving the crown exposed. This served as a practical measure, a sweatband for the toils under the unrelenting sun.
Headwear among seamen was dictated more by necessity than fashion. In the chill of the open sea, snug caps of wool or leather were favored, designed to withstand the force of the winds without being whisked away into the watery abyss. During storms, a tarred canvas hat, impervious to the rain, was the headgear of choice. Accompanying this, a cape of similar material offered some respite from the relentless onslaught of the elements. These items, collectively known as “sloppes,” were often communal, shared among those braving the deck during their watch.
In the balmier climes, the preferred hat was one of a lighter make, its brim narrow and circular, a modest shield against the blazing sun. This hat, unassuming yet functional, contrasted utterly with the lavish and often exaggerated attire of the Pirate captains, illustrating the dichotomy between the flamboyance of leadership and the pragmatism of the crew.
Furthermore, these buccaneers, infamous for their daring and debauchery, were often depicted in tales and images decorated with gold earrings and eyepatches, symbols of their roguish charm. Yet, contrary to popular lore, such accessories were scarce amongst the sea-faring folk of that age. The earring, a bauble of golden glimmer, was scarcely seen amongst these briny brigands. There exists a notion, albeit a fanciful one, that sailors wore these ornaments as a form of makeshift insurance — a fragment of gold set aside for the grim eventuality of a land-locked demise, ensuring a proper burial far from the ocean’s clasp. However, in truth, such effeminate adornments were the purview of Elizabethan courtiers, who bore them with a bravado often met with scorn and mockery.
Eyepatches, too, were not as prevalent as legend would have us believe. While the treacherous life aboard a galleon wrought many a peril, leading occasionally to the loss of sight, it was more common for these hardened seafarers to bear their scars with pride. The world of Piracy was one of brutal honesty, where the display of wounds exemplified a mariner’s seasoned tenure upon the high waves.
Yet, one accessory did find favor among these maritime outlaws. A sash, often of silk, draped across the chest functioned as a practical holster for their armaments. Into this sash, they would tuck pistols, secured with cords for swift release in the heat of battle, alongside other essentials like folding knives attached by lanyards. In the chill of the ocean breeze, they also donned knitted gloves or mittens, and their feet were shod in round-toed leather shoes, fastened with buckles or laces.
When these Pirates ventured ashore, particularly within Pirate havens, their attire transformed spectacularly. The drabness of their sea garb gave way to ostentatious displays of finery, plundered from the wealthy passengers of captured vessels. In these moments, the ordinary Pirate donned the guise of a dandy — velvet coats and jackets, taffeta breeches, silk shirts in vibrant tones, stockings prettified with ribbons, shoes with ornate buckles, and the exemplary tricorne hat. Armed with pistols and a cutlass, they presented a look of flamboyant richness, unlike their usual sea-worn appearance. Indeed, in their final, macabre parade to the gallows, these Pirates were arrayed in their most extravagant apparel, a defiant display of their indomitable spirit even in the face of death, ready to paint the town red for one last, short-lived moment.
Flags
In maritime lore, the Jolly Roger has marked its place with a grim and spectral visage. Its black canvas, stark against the unending blue of the seas, bore the macabre emblem of a skull and crossbones, as white as the bleached bones of the condemned. Far from the whimsical tales spun in taverns, this ensign was once a harbinger of doom, its mere unfurling enough to chill the marrow of seafarers and herald a fate most dire.
In that era of cutthroats and Corsairs, the Jolly Roger was not the sole flag of its kind, but a member of a ghastly pantheon of standards, each more sinister than the last. These banners, raised in the final, heart-stopping moments before an encounter, served a singular, bloodcurdling purpose. To behold such a flag was to be presented with a merciless ultimatum: surrender without delay, or brace for a savage onslaught, where mercy was as scarce as a calm sea in a tempest.
So feared were these Pirates that they would sometimes hoist an additional ensign, one steeped in crimson, as if the skies themselves bled at the sight. This red flag, unyielding in its message, foretold a fate devoid of quarter or compassion.
Amongst the pantheon of these terrifying sigils were flags adorned with skeletal figures, grim swords, and hearts oozing crimson lifeblood. The Pirates, cunning as they were ruthless, also flew the colors of various nations, a deceitful ploy to lull their prey into a false sense of security before the inevitable plunder and slaughter.
The moniker “Jolly Roger” was not always the exclusive appellation of the skull and crossbones flag. In its early days, it referred to any flag brandished by Pirates or their state-sanctioned brethren, the privateers. The origins of this sinister epithet are uncertain. Some contend it sprang from the term “Roger,” an olden name for the Devil, known colloquially as “Old Roger”. Indeed, a grim banner, depicting a skeleton clutching an hourglass and a bleeding heart, flown by Pirates hanged in Newport, Rhode Island, circa 1723, bore this ominous title.
Others argue that the term traces back to the vagabonds of the sea, often dubbed “Sea Beggars,” particularly in the Dutch tongue. Still, others muse that the name derived from the French “le jolie rouge,” alluding to a crimson flag long flown by privateers. This theory gains credence when one considers the Welsh Pirate Black Bart Roberts, known as much for his sartorial predilection for bright red silks as his fearsome reputation. His flag, too, was the Jolly Roger, and thus, by association, the name became lastingly linked to that black and white symbol of death and defiance upon the high seas.
Before the infamous Jolly Roger cast its spectral shadow across the briny deep, mariners and Pirates had long employed sinister symbols of skulls and bones upon their flags. Yet, it was not until the dawn of the 18th century that this macabre emblem truly began to carve its niche in the records of nautical notoriety. The earliest chronicled instance of such a flag adorning a vessel’s mast was in 1700, when Emmanuel Wynne, a Breton Corsair of some repute, unfurled a black standard off Santiago. His flag was no mere skull and crossbones; it bore an hourglass too, as if to remind all who gazed upon it of the inexorable passage of time and the imminence of death.
Despite Wynne’s pioneering display, it was primarily the British and American buccaneers who embraced the Jolly Roger with fervor in the early 18th century. This adoption came after a century wherein the unadorned black flag had already instilled terror in the hearts of seafarers. Pirates like Christopher Condent, who terrorized the Caribbean and Pacific from 1668 to 1672, brandished an embryonic form of the Jolly Roger, decorated with a trio of skulls and accompanying crossbones.
Richard Worley, another notorious British Pirate who met his end in Charleston in 1718, flew a variant of the flag, with the skull mounted atop the crossbones. Edward England, whose name thundered through the Caribbean between 1717 and 1720, was known to hoist the Jolly Roger in a form familiar to modern eyes. He did so with a dramatic flair, flying it alongside the Union Jack and a blood-red flag. Henry Jennings, an Englishman who carved his name into the lore of Piracy between 1715 and 1717, also flew the now-iconic Jolly Roger.
The symbolism of these flags was not lost on their contemporaries. Captain Snelgrave, in 1719, remarked that the Jolly Roger was a portent, a harbinger of doom intended to coerce honest merchants into abject surrender, under threat of merciless slaughter. It was widely understood that the black flag served as an initial warning. Should this ominous signal go unheeded, the hoisting of a red flag spelled the certainty of no quarter. Such was the grim protocol recounted by Captain Richard Hawkins in 1724.
Despite its relatively short-lived heyday in the history of Piracy, the Jolly Roger’s legend burgeoned, immortalized in the pages of literature. R. M. Ballantyne’s The Coral Island, penned in 1858, and Robert Louis Stevenson’s Treasure Island, first serialized in 1881, embedded the Jolly Roger in the public consciousness. These tales depicted it as the unmistakable standard of Piracy, its meaning recognized universally. As the curtain rose on the era of Hollywood, from the silent films to the cinematic extravaganzas of the 21st century, the Jolly Roger further cemented its place in the pantheon of iconic symbols, transcending its historical origins to become a timeless emblem of Piracy and adventure on the high seas.
Many flags were enhanced with images of skeletons, skulls, bleeding hearts, and hourglasses, each a chilling portent of mortality. These emblems, familiar from the gravestones of the period, spoke a universal language of dread and finality. Weapons, too, were a favored motif amongst these seafaring brigands. Swords, cutlasses with their sinister curves, flaming cannonballs, and spears were often depicted, each demonstrating the Pirates’ martial prowess and merciless nature. John Rackham flew a black flag emblazoned with a white skull above two crossed cutlasses. His standard was as distinctive as his nickname and as fearsome as his reputation.
The notorious Henry Every, scourge of the Red Sea and the Atlantic from 1692 to 1695, chose for his flag a human figure, one hand grasping an hourglass, the other a heart impaled by a spear, bleeding profusely. Edward Teach, perhaps the most infamous Pirate of all, is said to have flown a flag of similar design, but with a
macabre twist: the human figure was replaced with a skeleton, heightening the sense of terror.
Black Bart Roberts, with a penchant for theatrics, opted for a flag that was both ominous and whimsical. It depicted him indulging in a cup of wine, accompanied by a skeleton or devil clutching a burning spear. This self-aggrandizement extended to his personal banner, which portrayed him with a sword, triumphantly standing over two skulls marked ABH and AMH. These initials were a brazen affront to the governors of Barbados and Martinique, who had relentlessly pursued him, symbolizing their decapitated heads.
Some Pirates, perhaps overwhelmed by the plethora of sinister symbols at their disposal, chose to adorn their flags with a cluttered array of emblems. An example, attributed to Christopher Moody, albeit possibly erroneously, showcased a skull, crossbones, a sword, and an hourglass with wings, all set against a blood-red backdrop.
Indeed, in the world of Piracy, the flag was more than mere fabric; it was a symbol, a statement. Some captains, in a bid to drape their nefarious deeds in a cloak of legitimacy, flew the colors of their benefactors — be it a family emblem or a national standard. The British Admiralty in 1694 decreed that privateers under the Crown’s employ should sail under “The Red Jack,” alongside the Union Jack. The privateers of America, not to be outdone, unfurled red ensigns decked out with horizontal alabaster stripes.
Yet, in this world where deception was as common as the salt in the sea, some Pirates wielded flags not as badges of honor, but as tools of treachery. John Deane, an English marauder of the Caribbean in the 1670s, was a master of this ruse. With the cunning of a fox, he would raise Dutch, Spanish, or French colors, luring unsuspecting vessels into a deadly trap. In a twist of irony, the authorities often employed the same tactic.
The content in this article was taken from my new book, The Book of Pirates and Corsairs: Part I: Ageless Seas of Infamy:
Note: The images in this article have been generated, with the exception of William Hogarth’s engravings and the pirate flags (available in the public domain).
