When you think of piracy, names like Blackbeard and Calico Jack immediately spring to mind. Yet there exists a shadowy roster of seafarers who never earned the Hollywood spotlight but still managed to carve out impressive legacies. In this roundup we present ten obscure yet successful pirates, each a fascinating blend of grit, cunning, and sheer audacity.

10 Obscure Yet Pirates You Should Know

10 Pier Gerlofs Donia “Big Pier”

Pier Gerlofs Donia, a burly 15th‑century farmer from the Frisian town that now lies within the Netherlands, turned to piracy after his home was sacked and his wife assaulted. Towering and muscular, he earned the nickname “Big Pier.” He organized a militia called the Arumer Black Heap and waged a relentless guerrilla war against the Holy Roman Empire. Whenever he captured a suspect, he forced them to recite the tongue‑twisting phrase Bûter, brea en griene tsiis: wa’t dat net sizze kin, is gjin oprjochte Fries – roughly “Butter, bread, and green cheese: if you can’t say that, you’re not a true Frisian.” The phrase proved difficult for Dutch or German tongues to manage.

On land Donia was a terror wielding a massive Zweihander greatsword that reportedly stretched over two metres (seven feet). At sea he proved equally shrewd, seizing roughly a hundred vessels for the “Cross of the Dutchman.” Many of those merchant ships were refitted as troop transports, swelling his army’s mobility. Although his original aim was Frisian independence, internal squabbles eventually drove him away from the cause. By 1519, after barely four years of conflict, Donia retired to a quiet life, slipping away in his sleep the following year.

9 Cornelis Jol “Pegleg”

Cornelis Jol, affectionately called “Houtebeen” (Dutch for Pegleg), lost his leg to a cannonball as a boy. A 17th‑century Dutch corsair, he concentrated his raids on Spanish vessels in the West Indies after serving in the Dutch navy and joining the West India Company in 1638.

More a privateer than a full‑blown pirate, Jol became a folk hero in the Netherlands for his role in turning the tide against Spanish and Portuguese forces in the New World. The Spanish even sang a mocking song about him that began, “Peg‑leg is a bad pirate, who eats raw octopus and drinks sea water.” His wooden leg made him one of the earliest captains known for such a prosthetic, cementing his place in nautical lore.

8 Jean Lafitte

Jean Lafitte, a French‑born buccaneer, launched his career just after the turn of the 19th century, prowling the Gulf of Mexico under the unrecognised flag of Cartagena, a Colombian city that had declared independence. He also operated as a smuggler, moving contraband and slaves into the United States. Though he blamed American policies for his turn to crime, Lafitte fought alongside the U.S. against the British during the War of 1812.

The British first tried to recruit him, but Lafitte feigned cooperation while feeding them false intelligence. He later approached the American government, offering his services in exchange for pardons for himself and his crew. The U.S. accepted, and many of his men settled into respectable lives after the war. Yet Lafitte could not stay ashore; he resumed piracy near Texas until around 1820, and the circumstances of his death remain a mystery.

7 Laurens de Graaf

Laurens de Graaf, another 17th‑century Dutch marauder, earned the reputation of a gentleman outlaw. He was known to travel with violins or trumpets, which he would play for his crew during long voyages. After a respectable stint as a sailor, a loss of employment and a subsequent capture by pirates pushed him over the edge.

Accounts of his early life differ—some claim he was a Spanish prisoner or slave sent to the Americas as punishment. Regardless, de Graaf ended up in the West Indies, where he seized the famed Tigre, a captured 24‑gun Spanish man‑of‑war. For decades he raided Spanish and English outposts across the Gulf of Mexico and beyond. Despite numerous pirate hunters on his trail, he evaded capture and eventually retired to the southern United States, where he is believed to have died.

6 Roberto Cofresi “El Pirata Cofresi”

Roberto Cofresi, a celebrated figure in Puerto Rico, operated as a pirate during the 19th century. Initially a merchant sailor, he turned to piracy in his twenties due to severe economic hardship on his island. Early on he targeted American vessels, especially those transporting gold.

Because the island remained under Spanish rule, colonial authorities largely ignored his activities, even when the United States pressed for his capture. As Spanish oppression of native Puerto Ricans intensified, Cofresi broadened his list of victims to include Spanish ships, earning the ire of the crown. He built a complex network of contacts that helped him evade capture for years, and his Robin‑Hood‑like reputation endeared him to the public. In 1825 his luck ran out; Cofresi and eleven of his men were executed.

5 François l’Olonnais “The Bane Of The Spanish”

Born Jean‑David Nau, the French privateer later known as François l’Olonnais harbored an all‑consuming hatred for Spain after serving as an indentured servant to Caribbean Spaniards. Once freed, his fury manifested in a ferocious campaign against Spanish interests throughout the 17th century.

L’Olonnais was notorious for extreme cruelty—legend tells of him dissecting a prisoner, biting the heart, and hurling it at a companion. His most celebrated feat was the swift capture of the supposedly impregnable Venezuelan town of Maracaibo, whose 16‑gun fort had long been deemed unassailable. Using brilliant tactics, he overran the fort in a matter of hours. He then terrorised the town’s inhabitants until they revealed hidden treasure. After a later shipwreck on the coast of Cartagena, he met his demise on the island of Darien, where indigenous inhabitants tore him apart limb by limb.

4 Rahmah ibn Jabir “The Scourge Of The Pirate Coast”

Rahmah ibn Jabir, a Bahraini corsair who thrived at the turn of the 19th century, earned the moniker “The Scourge Of The Pirate Coast.” His clan, Al Jalahma, had been locked in a two‑decade feud with the rival Al Khalifah clan, a rivalry that fueled much of his piratical activity.

By deliberately sparing British ships, ibn Jabir avoided provoking the Crown, focusing his aggression on Al Khalifah and other regional powers. At his zenith, nearly two thousand men—many of them freed African slaves—served under his banner. He endured severe injuries, losing an eye and most use of his right arm. His ruthless reputation eventually united Arab forces against him, and in 1820 he was finally defeated. Refusing to be captured by his enemies, he detonated barrels of gunpowder aboard his vessel alongside his eight‑year‑old son, ending his life and that of his crew in a fiery finale.

3 Olivier Levasseur “The Buzzard”

Olivier Levasseur, better known as “La Buse” (the French for “The Buzzard”), prowled the Caribbean in the early 18th century before shifting his operations to the Indian Ocean. His nickname reflected the speed and ferocity with which he struck his foes.

After being cast out by fellow buccaneers, Levasseur captured the crippled Portuguese vessel Nossa Senhora del Cabo near Réunion Island in 1721. The ship was laden with untold riches and valuable religious relics. The French authorities, alarmed by his growing power, finally apprehended him. He was tried, sentenced, and hanged. In his final moments, he tossed a mysterious necklace and cryptic papers into the crowd, challenging anyone to locate his hidden treasure—a bounty that remains unfound to this day.

2 Samuel Bellamy “Black Sam”

Samuel Bellamy’s pirate career was astonishingly brief—barely a year or two—but it was spectacularly lucrative. Dubbed “Black Sam,” he amassed an estimated $120 million in modern dollars, making him the wealthiest pirate on record.

Initially a treasure hunter who came up empty‑handed, Bellamy turned to piracy, eventually securing a ship and a loyal crew. He governed his vessel with a quasi‑democratic system that earned him the devotion of his men. Known for his mercy toward captured sailors, he led his “Robin’s Hood Men” to seize over fifty ships across the Caribbean and Atlantic. His crowning achievement was the capture of the English slave ship Whydah, brimming with over 20,000 pounds sterling. The crew set sail for Massachusetts, only to be wrecked by a ferocious storm that sank the Whydah, sparing just two survivors.

1 Aruj “Redbeard”

Aruj, born in the 1470s to a Turkish father and Greek mother on the island of Lesbos, endured brutal oppression at the hands of the Knights of Saint John. After three years of enslavement, he escaped with a burning desire for vengeance. Together with his brother Hizir, he became a feared Mediterranean raider, initially serving as a privateer for Egyptian interests.

During a siege of a Spanish‑captured port, Aruj suffered a severe arm injury that required amputation. Both brothers earned the nickname “Barbarossa,” meaning “Redbeard,” due to their striking hair color. Their piracy made them among the richest men of the era. After numerous clashes with Spanish and even Muslim fleets, Aruj fell in battle, leaving his fortune to his brother. One of his most audacious acts was the capture of the Pope’s own trading galley off the coast of Elba.

When you think of piracy, the Caribbean’s golden age of privateers and the infamous names of Blackbeard, Anne Bonny, and Captain Morgan probably spring to mind. Yet the Pacific Ocean hid its own legion of daring, cut‑throat marauders who ruled the seas with iron fists and glittering treasure. In this roundup we spotlight the 10 brave bloodthirsty pirates who prowled the Far East, each a larger‑than‑life character whose deeds echo through history.

10 Brave Bloodthirsty Pirates Unleashed

10 Lai Choi San

Back in 1956, adventurer‑author Aleko Lilius released I Sailed with Chinese Pirates, a memoir that remains the most vivid source on the legendary female commander Lai Choi San. Lilius claims he earned the trust of this notorious pirate queen and became one of the few Westerners ever allowed aboard her fleet, giving us a rare glimpse into her world.

According to Lilius, Lai Choi San first appeared to him as a Robin‑hood‑type figure of the South China Sea, raiding wealthy merchant vessels and then distributing the spoils among the impoverished coastal communities. He admits, however, that he could not separate fact from the many tall tales that swirled around her name; at first he even doubted her existence until he finally met her in person.

Dubbed the “Queen of the Macau pirates,” Lai Choi San inherited a thriving criminal enterprise from her father, who had secured a semi‑official protectorate from the colonial government in exchange for safeguarding local fishermen from rival gangs. The title of “inspector” bestowed upon her granted official immunity, allowing her to run protection rackets and kidnapping schemes without fear of government retaliation.

Lilius notes that she amassed “barrels of money” from these operations, ruling her crew with an iron fist while demanding ransoms for kidnapped men, women, and children. Though historians debate how much of Lilius’s account is embellished, most agree that Lai Choi San was a formidable force in the South China Sea, wielding both political cover and ruthless ambition.

9 Limahong

Limahong’s fleet cut a swath through the coastal waters of China during the 1570s. Born in Tui‑Chiu, he joined the crew of the pirate Tia‑La Ong as a teenager, quickly rising through the ranks. When Tia‑La Ong fell in battle, Limahong assumed command, inheriting not only the ships but also a delicate relationship with the Ming emperor, who tolerated his raids in exchange for a thin veneer of cooperation.

When the emperor grew impatient with Limahong’s relentless attacks on Chinese villages, a hefty bounty was placed on his head. Seeking fresh opportunities, Limahong seized a Manila‑bound vessel, lured by rumors of untapped riches in the Spanish Philippines, and plotted to establish a new base of operations there.

In November 1574, Limahong led an armada of roughly 74 ships and 2,000 warriors (some accounts inflate those numbers to 200 ships and 10,000 men) into Manila Bay. The first foray was a night‑time test of the city’s defenses, but it quickly devolved into chaos when the camp master’s wife mistook the invading force for angry natives and shouted, “Go away, dogs, or you will all die today!” The miscommunication set the tone for a brutal showdown.

The pirates regrouped, launched a second assault, and set fire to the Spanish camp. In a grisly display, the pirate chief presented the severed ears and nose of the camp master, Martin de Goiti, to his own men. Reinforcements arrived, forcing the pirates to retreat, but Limahong quickly shifted his focus to raiding nearby Spanish settlements, continuing his campaign of terror.

Limahong’s general, who had overseen the first attack, later lied to him, claiming their landing site was too distant for a full assault. The delay allowed Spanish forces to bolster their defenses, and after three days the pirates launched a full‑scale invasion that was finally repelled. Undeterred, Limahong turned his attention to other coastal villages, pillaging wherever he could.

By August 1575, a joint Spanish‑Chinese effort nearly trapped Limahong, but he slipped away, disappearing from the historical record after a final sighting near Guangdong. His legacy endures as a daring, if ultimately elusive, figure who challenged both Chinese and European powers in the Pacific.

8 Shirahama Kenki

Shirahama Kenki began his career as a bona‑fide pirate, but his voyages soon turned exploratory. In 1585, his fleet of five ships made an unexpected appearance off the coast of what the Japanese of the era called Cochinchina—modern‑day Vietnam—where locals initially mistook him for a European trader.

Kenki’s raiding parties quickly targeted villages along the coastline, prompting a response from Nguyen Hoang’s sixth son. The young lord’s forces managed to destroy two of Kenki’s vessels, forcing the pirate to retreat. Yet Kenki was not deterred; sixteen years later he returned, this time under a more diplomatic guise.

When his ship wrecked in a Vietnamese port, the local magistrate, unaware of Kenki’s true identity, treated him as a lawful merchant. The magistrate’s death—whether by accident or design—allowed Kenki to avoid execution. Nguyen Hoang, recognizing the potential benefits of a sanctioned trade route, wrote to the Tokugawa shogun, praising Kenki’s handling of the incident and paving the way for the issuance of “red‑seal” permits that legitimized Japanese‑run commerce in the region.

7 Eli Boggs

Eli Boggs, an American who turned pirate in the bustling harbor of Hong Kong, earned a reputation as a strikingly handsome criminal with “lily‑white” hands and a delicate, almost feminine demeanor. Despite his appearance, he proved as ruthless as he was good‑looking, eventually being captured and tried for piracy and murder.

During his trial, Boggs claimed he was a pawn in a larger conspiracy orchestrated by the notorious gangster Wong Ma‑Chow, who allegedly acted under the direction of Daniel Richard Francis Caldwell—the British Secretary for Chinese Affairs in the 1850s. Caldwell, a former merchant turned colonial official, allegedly leveraged his extensive network of informants to both suppress piracy and control the region’s vice‑laden brothels.

Boggs delivered a two‑hour, eloquent testimony that accused Caldwell of using his official position to shield his own criminal enterprises, including the licensing and ownership of brothels. The accusations sparked what became known as the “Caldwell Affair,” a scandal that exposed deep corruption within the colonial administration and cemented Hong Kong’s reputation as a hotbed of vice.

Although the court convicted Boggs of piracy, the lack of concrete evidence linking him to murder meant he escaped a death sentence. Instead, he was deported from Hong Kong, his fate a cautionary tale of how a seemingly genteel pirate could become entangled in a web of colonial intrigue.

6 William Henry Hayes

Born in Cleveland, Ohio, around 1829, William “Bully” Hayes earned his moniker through a life of relentless ambition and scandal. After mastering sailing on the Great Lakes, he ventured into the Pacific, first appearing in Australian records in 1857, where his reputation as a cunning swindler quickly spread.

Hayes built a criminal empire by convincing ship owners and captains to sign over their vessels in exchange for a promised share of cargo—promises he never intended to keep. His personal life was equally tumultuous; he married Amelia Littleton and later Rosa Buckingham, the latter meeting a tragic end alongside her child, brother, and servant. In 1860, he faced charges of indecent assault and spent time “blackbirding,” luring unsuspecting individuals into forced labor under false pretenses.

By 1874, Hayes reportedly accumulated five additional wives, a testament to his unbridled hedonism. Growing public outrage over his violent exploits forced him to abandon his trading post in the Caroline Islands. He escaped on a whaling ship to San Francisco, where he once again commandeered a vessel—this time with another man’s wife aboard—for what would become his final voyage.

Hayes’ ultimate fate remains shrouded in mystery; most accounts agree he met his end in a violent altercation with a fellow sailor, his body tossed overboard without ever facing formal conviction. The blend of fact and fiction surrounding his life makes him one of the Pacific’s most enigmatic and brutal characters.

5 Shap‑Ng‑Tsai

Shap‑Ng‑Tsai began his criminal career as a smuggler in the chaotic aftermath of the First Opium War. With Hong Kong officially a British colony after 1842, the new trade treaties made smuggling more lucrative than legitimate commerce, prompting many illicit traders to adopt pirate tactics.

From his base in what is now Dianbai, Shap‑Ng‑Tsai launched a protection racket, offering to escort and safeguard smugglers for a fee. By 1849 his fleet had swelled to an astonishing 70 vessels, stretching from China’s coast down to Vietnam. While this operation initially escaped serious scrutiny, the fleet’s attacks on British and American merchant ships—protected under newly signed treaties—prompted a swift response from the Royal Navy.

Shap‑Ng‑Tsai proved a master of deception. When the Royal Navy moved to seize his seized ships, he cleverly allowed his captured vessels—roughly 100 in number—to be auctioned back to him, then tacked the purchase price onto his ransom demands. In October 1849, a decisive naval battle destroyed 58 of his ships, including his flagship, and claimed about 1,700 of his crew’s lives. Yet the crafty pirate escaped, later being bought out by the Chinese government and re‑appointed as a respectable naval officer.

4 Wang Zhi

Wang Zhi started his career as a salt merchant during the Ming dynasty, a period when the government imposed heavy taxes on the lucrative salt trade. Frustrated by the fiscal burden and the constant harassment from coastal pirates, Wang sought protection by hiring Japanese pirates, eventually forming his own seafaring syndicate that blended commerce with outright piracy.

His operation grew to encompass the transport of European firearms—handguns and cannons—into Asian markets, while simultaneously exporting gunpowder and its essential ingredients. This trade made him a vital conduit between Portuguese merchants and the East, and he even encouraged the spread of Christianity, believing that missionary activity could bring technological advantages.

Wang’s ambitions, however, clashed with the Tokugawa shogunate’s growing suspicion of foreign influence. In 1559, the shogunate cracked down on his activities, leading to his execution. His downfall illustrates how the line between legitimate trade and piracy could blur, especially when political and religious currents intersected.

3 Cai Qian

Cai Qian’s piratical career was brief yet ferocious. Originating as a humble peasant‑turned‑fisherman, he joined a pirate crew in 1795 and quickly rose through the ranks, employing ruthless tactics—including using his own wife as bait—to eliminate rivals and secure his own command.

By 1800, provincial authorities took notice after a heavily armed ship under his control was captured. Interestingly, Cai’s crew operated without a formal hierarchy; there were no official captains or titles, a structure that initially confused officials and bought him precious time before a concerted crackdown began.

When a massive typhoon in 1800 destroyed many vessels from rival fleets, the remaining pirate bands coalesced under Cai’s banner, and he boldly declared himself the “King to Pacify the Oceans” in 1806. His growing power alarmed the Qing government, which launched a campaign of smaller, targeted vessels to cut off his supply lines. The strategy succeeded, and in 1809 government forces finally cornered and killed Cai at sea.

2 Charlotte Badger

Charlotte Badger was born in Worcestershire, England, and baptized on July 31, 1778. In 1801 she was transported to Sydney after being convicted of breaking into a house, receiving a seven‑year sentence. Two years shy of completing her term, she and a fellow convict were assigned as servants to a settler family bound for Tasmania.

During the voyage, a mutiny erupted among the convicts. Badger emerged as a pivotal figure—some accounts credit her with rallying the rebels, whipping the ship’s captain, and leading a daring raid on another vessel to seize weapons and supplies. Together with her ally Catherine Hagerty, she escaped with a fellow convict and the ship’s first mate, commandeering a vessel loaded with provisions sufficient to establish a new settlement.

The mutineers set up a makeshift colony at Rangihoua Bay in New Zealand, but the group soon fragmented. Some, including the first mate, returned to Europe, while Hagerty died. Badger remained among the Maori, integrating into their community. Later rumors suggest she either perished there, was kidnapped, or managed to reach the United States, but the exact details of her final years remain shrouded in mystery.

1 Cheng Ch’i And Ching Shih

When Cheng Ch’i’s pirates seized a brothel, he chose one of the courtesans to become his wife, forging a partnership that would blossom into one of the most formidable pirate empires in history. The union produced a powerful fleet under the command of the former prostitute, Ching Shih, who would later be known as Cheng I Sao.

For six years Cheng Ch’i and Ching Shih ruled the South China Sea together, until a devastating typhoon claimed Cheng’s life. Ching Shih immediately assumed command, promoting the 21‑year‑old Chang Pao—her late husband’s protégé and former lover—to the rank of lieutenant. Under her iron‑fisted leadership, the fleet grew to an astonishing 1,600 ships and over 70,000 pirates, spies, and agents.

Ching Shih imposed a strict code of conduct: her crew could not plunder villages that had provided them with food or aid, and any act of rape was punishable by death. Pirates wishing to keep a captive woman had to marry her and treat her respectfully, with infidelity leading to execution. In return for unwavering loyalty, she ensured her sailors were well‑armed, well‑supplied, and even provided a rudimentary pension system.

Eventually Ching Shih negotiated an amnesty with the Chinese authorities. While the precise terms remain debated, one popular story claims she avoided direct humiliation by marrying Chang Pao, who then performed the official ceremony, satisfying the governor’s requirement without compromising her dignity. After retiring, she either ran a smuggling operation, a brothel, or both, and lived to the ripe age of 69, a remarkable longevity for a pirate of her era.

They set sail across the Caribbean in pursuit of treasure, each driven by a different motive—some were idle soldiers, others privileged thrill‑seekers, and one was a penniless sailor hoping to win his beloved’s hand. Yet, of the world’s most infamous pirates featured below, every single one met a grim fate—hanging, drowning, or a blade’s cruel kiss—except for a lone survivor.

10 The Pirate King And The Flying Gang

Benjamin Hornigold, an English privateer, kept fighting the Spanish even after the 1713 war ended. Until then, the Crown had granted him permission to seize enemy vessels and off‑load their loot in Port Royal, Jamaica.

In 1715, he launched a daring raid on Spanish divers trying to salvage a treasure galleon. Though the raid succeeded, the Jamaican governor rebuffed his attempt to sell the plunder. After the war, Britain’s new access to Spanish sugar, rum, and the slave trade made privateering less welcome; the Crown demanded that all privateers either cease their raids or be branded pirates.

Left without a commission, a market, or a fleet to sustain, Hornigold turned to the black market, establishing a base in Nassau, a modest Bahamian port.

Once Hornigold’s crew arrived, the local governor could do nothing as they bullied residents and seized control, calling themselves the “Flying Gang.” Word of their riches spread, drawing sailors and cutthroats from far and wide. Hornigold earned the title of “king” of this fledgling pirate republic.

9 The Gentleman Pirate

Stede Bonnet, a wealthy Barbadian landowner, grew weary of his complacent life and, irritated by his nagging spouse, dreamed of piracy. He spared no expense in commissioning a vessel he christened The Revenge, a popular ship name of the era, recruited a crew, abandoned his wife, and set course for Nassau to join the Flying Gang.

Bonnet’s lack of nautical skill quickly cost him the crew’s respect; he knew nothing of navigation. After a severe wound in a disastrous clash with a Spanish warship, he feared mutiny and loss of control.

In Nassau, Bonnet met pirate king Hornigold and his fiery apprentice Edward Teach. Teach agreed to mentor Bonnet on the condition that Bonnet surrender command of his splendid new ship to Teach. Bonnet obliged, taking over Teach’s former vessel.

Teach, later infamous as Blackbeard, used terror tactics—lighting fuses in his hat to appear demonic—to seize ships with minimal bloodshed. Though Bonnet never achieved the same reverence, after a botched merchant capture, his crew deserted him for Blackbeard, who, out of pity, let Bonnet remain aboard The Revenge as a guest.

8 The Prince Of Pirates

In 1715, Sam Bellamy, a destitute sailor, fell for Mary Hallett, the daughter of a prosperous farmer, during a night of revelry in a Massachusetts tavern. Their whirlwind romance ended when Mary’s parents rejected his proposal, deeming him too poor.

Determined to win Mary’s hand, Bellamy quit his job, crossed the Atlantic, and attempted treasure hunting without success. He eventually joined the Flying Gang, where his natural aptitude for piracy caught the eye of Hornigold, who was scouting a successor after Blackbeard’s departure.

Under Hornigold’s tutelage, Bellamy honed his pirate craft, yet still lacked the funds to marry Mary and grew impatient. Hornigold’s reluctance to attack British and Dutch ships left treasure unclaimed, prompting the crew’s frustration.

In July 1716, the crew voted to depose Hornigold and install Bellamy as captain. Hornigold received a smaller vessel to return to Nassau, retaining his status as pirate king among the locals.

7 Robin Hood Of The Seas

Sam Bellamy quickly rose to become one of history’s most successful pirates, dubbing himself the “Robin Hood of the Seas” for plundering affluent merchants and redistributing wealth to impoverished sailors.

He sported a satin bow to tie back his dark hair—an unusual fashion choice at a time of powdered wigs—wore a velvet coat, a cutlass at his waist, and four pistols tucked into his sash. His charismatic presence earned him the moniker “Black Sam Bellamy,” and his fleet swelled to nearly two hundred men.

In 1717, Bellamy seized the massive, opulent Whydah Galley, the Caribbean’s most valuable ship, making him the wealthiest pirate ever. He set sail for Massachusetts to reunite with Mary, but a fierce hurricane wrecked the Whydah, drowning Bellamy and all but ten of his crew.

6 The Royal Pardon

While Hornigold lingered in Nassau, news arrived that the Crown dispatched a new governor, Woodes Rogers—a former privateer—to eradicate piracy. Backed by the British Navy, Rogers blockaded Nassau’s harbor, preventing any departure.

Representing the pirates, Hornigold negotiated with Rogers, who extended a universal offer: surrender by September 5 1718 and receive a full pardon for all piratical crimes; refuse, and face the gallows. Hornigold seized the chance to re‑enter Crown service as a pirate hunter.

Hornigold not only accepted the pardon but persuaded many comrades to do the same. Meanwhile, Blackbeard grounded his ship and secured a pardon in the Carolinas, leaving Stede Bonnet abandoned because he refused to renounce piracy.

Opposition to the pardon grew among pirates like Charles Vane and his quartermaster Calico Jack, who fled Nassau by igniting a flaming, exploding vessel to breach the blockade. Governor Rogers tasked Hornigold with tracking down Vane.

5 Pirate Hunters

Hornigold pursued Vane for months, but Vane’s formidable fleet proved too strong for a direct assault, despite Hornigold’s capture of several pirates trading with Vane. Ultimately, Hornigold returned ten pirates to Governor Rogers for execution.

Rogers praised Hornigold’s efforts but sent him out again to capture Vane. During this final mission, a violent storm sank Hornigold’s ship, and he vanished at sea, never to be seen again.

Later, Hornigold sailed to North Carolina to rendezvous with Blackbeard. Vane proposed a joint attack to retake Nassau, but Blackbeard preferred to continue his operations in the Carolinas, where authorities turned a blind eye. Their revelry attracted the attention of the Virginia governor, who grew uneasy about nearby piracy.

One night, while Blackbeard’s crew was heavily intoxicated, the governor dispatched the Royal Navy to annihilate them. After a fierce clash, Blackbeard boarded the British vessel, only to find troops concealed below deck. They killed him, severed his head, and displayed it on the mast.

4 Mutiny

Charles Vane proved nearly untouchable by the British Navy, eluding capture while other pirate hunters secured Stede Bonnet, who ultimately faced execution.

Vane’s reputation for cruelty toward prisoners and crew members sowed discontent. After refusing to attack an intimidating French vessel, his quartermaster Calico Jack Rackham demanded Vane’s removal for cowardice. The crew agreed, sending Vane away on a modest sloop.

Months later, while rebuilding his fleet, Vane’s ship ran aground during a hurricane off Honduras. Stranded on an island, he survived months before a passing vessel rescued him. However, a former prisoner recognized him, leading to Vane’s arrest in Port Royal, trial, and hanging in November 1720.

3 A Bonny Lass

Anne Bonny, a spirited Irishwoman, grew up under a wealthy father’s roof in the Carolinas. Legend claims she once stabbed a servant in a fit of rage. She married sailor‑turned‑pirate James Bonny, and together they sailed to the Bahamas seeking fame and fortune.

Upon arrival, James abandoned the pirate life, accepted the king’s pardon, and entered Governor Rogers’ service. Bored and resentful, Anne frequented taverns, where she encountered the flamboyant, inebriated pirate Calico Jack Rackham.

Jack, having secured his own pardon to avoid capture, found himself stuck in Nassau, restless. Anne captivated him, sparking a passionate affair. When Jack offered James a sum to release Anne from marriage, James reported the betrayal to Governor Woodes Rogers.

Rogers ordered Anne’s return to her husband, to be stripped and publicly flogged. Defying the decree, Anne and Jack seized a vessel, fled Nassau, and resumed their piratical pursuits.

2 Lover’s Key

Anne Bonny, a fierce pirate, and Jack Rackham captured numerous ships during their honeymoon, selling the spoils. When a Spanish sloop crippled their mainmast, the wind drove them toward an island later known as Lover’s Key.

The crew ventured inland to harvest timber for repairs, while Jack and Anne stayed ashore, sheltering in a makeshift hut of sticks and palm leaves. By the time the ship was fixed, Anne was pregnant. Unwilling to abandon piracy for motherhood, she left her newborn son with a retired pirate couple in Cuba.

Subsequently, the duo seized a Dutch vessel, compelling many Dutch sailors to join their ranks. Among the new recruits was Mary Read, a tomboy who wielded a cutlass as deftly as Anne, forging a strong camaraderie that sparked a tinge of jealousy in Jack.

1 Calico Coward

While hiding in Nassau, Calico Jack, Anne Bonny, and Mary Read absconded with the fastest Bahamian sloop. Governor Rogers, exasperated by their mischief, dispatched renowned pirate hunter Captain Barnet to chase them.

Celebrating a recent capture, Jack and his male crew became heavily intoxicated, while Anne and Mary, wary of Barnet’s pursuit, fought the hunters on deck. When Barnet boarded, the drunken men concealed themselves in the cargo hold, leaving Anne and Mary to confront the attackers.

Enraged by Jack’s cowardice, Anne fired a shot into the cargo hold, shouting, “If there’s a man among ye, ye’ll come out and fight like the men you are thought to be!” Yet the men remained hidden, and the women were overwhelmed.

Ultimately, Jack and the rest of the crew surrendered after the pirate hunters discovered them concealed in the hold.

+ The Gallows

Calico Jack and his crew were tried and sentenced to hang on 16 November 1720. While imprisoned, Anne saw Jack one last time and lamented, “I am sorry to see you here, Jack, but if you had fought like a man, you needn’t hang like a dog.” Jack’s corpse was displayed in a gibbet near Port Royal on Dead Man’s Cay.

Anne and Mary faced separate trials; both were convicted but claimed pregnancy, which forced the courts to stay their executions, as the law prohibited executing a pregnant woman.

In April 1721, Mary succumbed to fever in her cell. Anne’s fate remains a mystery—no records of her execution, death, or release exist. Some speculate her affluent father bribed officials to secure her freedom, allowing her to return to Charles Town, South Carolina, remarry, and raise a family.

For more of Matt’s narrative history lists, explore “10 Steps In The Rise Of The Aztec Empire” and “10 Fateful Moments In The Fall Of The Han Dynasty.” Visit his blog for all his compilations.

While legendary buccaneers such as Blackbeard and Calico Jack often dominate popular imagination, a shadowy roster of lesser‑known marauders also carved a permanent scar into the annals of seafaring horror. In this roundup of 10 history s, we shine a lantern on those fearsome captains whose ruthless deeds still echo across the waves.

10 History S: The Most Brutal Buccaneers

10 Sadie The Goat

Sadie Farrell, a notorious gang chief hailing from New York’s underbelly, earned a reputation for driving her victims to the brink by head‑butting them straight into the gut before stripping them blind. Though her early criminal career involved petty theft, a dramatic encounter with the Charlton Street Gang’s botched sloop robbery ignited her ambition to become a pirate. Within days, she leapt into the fray, leading a daring seizure of a far larger vessel.

Her crew quickly became infamous for their coarse language and reckless daring, cruising the Hudson and Harlem Rivers to plunder other ships, raid coastal settlements, and snatch people for ransom. Tales of prisoners being forced to “walk the plank” circulated alongside the grisly legend of Sadie sporting a human ear around her neck – a gruesome trophy bitten off a rival gangster during a violent clash.

The Goat’s marauding reign persisted for several months until a coalition of local farmers amassed enough force to push them back. Defeated, Sadie retreated to land, yet her legacy endured, forever branding her as the “Queen of the Waterfront” in New York folklore.

9 Francois L’Olonnais

Born Jean‑David Nau to a destitute French family in the 1600s, Francois l’Olonnais was thrust into indentured servitude before eventually escaping to the bustling colony of Saint‑Domingue (present‑day Haiti). There, he immersed himself in the chaotic world of buccaneers, targeting Spanish‑laden vessels plying the West Indies trade routes.

After a disastrous shipwreck that left his crew brutally assaulted by Spanish troops, l’Olonnais swore vengeance. He rallied the surviving men on Tortuga, where they unleashed a savage raid that razed the town and annihilated an entire rescue party dispatched by the governor of Havana. Only a single sailor was spared, forced to bear witness to the carnage.

His notoriety stemmed largely from his love of torture. Among his favorite methods were cleaving chunks of flesh from captives with his sword and a gruesome technique called “woolding,” wherein a rope was tightened around a victim’s skull until the eyes burst forth.

Fleeing a renewed Spanish assault, l’Olonnais inadvertently grounded his crippled ship along Panama’s coast. While his men scrounged for provisions, they fell into the hands of the native Kuna tribe—cannibals who devoured both the pirate and his remaining crew, ending his reign of terror.

8 Nicholas Brown

Nicholas Brown, dubbed “The Grand Pirate” by his contemporaries, prowled the waters off Jamaica in the early 1700s. Though details of his youth remain murky, he quickly earned infamy by raiding English, Portuguese, and Spanish vessels throughout the Caribbean, amassing a fearsome reputation.

In a bid to curtail his depredations, colonial authorities extended a royal pardon, hoping to lure him back into lawful society. Brown initially accepted, but the allure of piracy proved too strong; he soon abandoned the straight‑and‑narrow life, prompting the Jamaican government to post a £500 bounty on his head.

His old schoolmate and naval adversary, John Drudge, seized upon the bounty with literal fervor. After tracking down Brown, Drudge slayed him, then decapitated his friend, preserved the head in a rum‑filled keg, and marched back to Jamaica to claim his reward, cementing a grisly episode in pirate lore.

7 The Victual Brothers

The Victual Brothers originated as a cadre of German mercenaries hired by King Albert of Sweden to wage war against Denmark during the 14th‑century conflicts. Rather than simply seizing enemy ships for the crown, the group swiftly morphed into a Robin Hood‑style fleet, plundering opulent merchant vessels to feed the starving and support the downtrodden.

During the siege of Stockholm by Queen Margaret of Denmark, the Victual Brothers executed a bold breakout, slicing through the blockade to deliver vital provisions, ammunition, and military aid to the beleaguered city’s populace.

Emboldened by their success, they established a permanent base on Gotland Island, turning the icy Baltic waters into a hunting ground. Their relentless attacks on any ship they encountered caused such panic among merchants and state vessels that Baltic trade ground to a near‑standstill.

In response, King Albert and Queen Margaret temporarily set aside their rivalry to jointly expel the marauders. By 1400, royal forces captured Klaus Stortebeker, a principal leader, and brought him to trial in Hamburg, where he met a swift beheading.

With Stortebeker’s execution, the remaining Victual Brothers were systematically hunted down and eradicated by Danish and Swedish authorities, ending their reign of terror in the Baltic Sea.

6 Edward Jordan

Edward Jordan’s brief yet ferocious piratical career began amid the Irish rebellion against the British Crown in 1798. Captured and sentenced to hang, he escaped, was recaptured, and ultimately bought his freedom by trading valuable insurgent intelligence for a royal pardon.

When Irish compatriots discovered his betrayal, Jordan fled across the Atlantic, settling in Gaspé where he secured a loan to purchase a schooner named Three Sisters. His inability to repay the debt led creditors to dispatch Captain Stairs in 1809 to seize the vessel.

Initially, Jordan appeared compliant, even requesting passage for his family aboard the schooner to secure honest employment. However, once the ship set sail, he brandished a pistol, attempted to shoot Captain Stairs, missed, and instead killed the first mate. Stairs escaped by leaping overboard.

Jordan commandeered the Three Sisters, steering toward Newfoundland with plans to recruit a new crew and flee back to Ireland. Yet a passing ship rescued Stairs, prompting a swift search for Jordan’s vessel. A bounty of £100 was offered for the capture of “Pirate Jordan.”

The schooner was intercepted off Newfoundland’s coast, and Jordan was tried, condemned to death, and his body tarred and displayed in chains at the harbor as a stark warning to other seafarers.

5 Edward Low

Edward Low entered the world in London as the son of a destitute family, turning to petty theft from a young age. After an early marriage, he and his wife ventured to the New World, only for her to die in childbirth, prompting Low to return to a life of crime.

He earned his pirate mantle after leading a mutiny aboard a sloop bound for Honduras, where he had been employed as a rigger. Unlike many of his contemporaries, Low kept his fleet modest—typically three or four ships—yet his cruelty knew no bounds.

Following a successful capture, Low would torture his captives before setting the seized vessel ablaze. Crew member Philip Aston recalled Low’s barbarity, noting that no English crew matched his savage reputation. Low’s preferred method involved binding a victim’s hands, threading rope between the fingers, then igniting the rope, scorching the flesh to the bone.

He also delighted in brutal cutlass assaults, famously cutting off the lips of the captain of the Portuguese ship Nostra Signiora de Victoria and subsequently broiling and force‑feeding them to the horrified captain. Low’s ferocity and reckless tactics made him the most feared pirate of the early 1700s, though his ultimate fate remains a mystery—rumors suggest a storm‑driven wreck, mutiny, or French capture and execution.

4 Black Caesar

Black Caesar, a towering figure reputed to have once been an African chieftain, was captured and shipped to the Americas as a slave. After a shipwreck off Florida’s coast, he and a companion commandeered a longboat, escaping the sinking vessel.

Disguised as shipwreck survivors, they lured passing vessels, then seized them at gunpoint, demanding provisions and valuables. Caesar amassed a modest fortune, which he allegedly buried on Elliot Key.

He later expanded his operations by capturing a larger ship and recruiting a crew, allowing him to venture into deeper waters while still haunting the Florida Keys. Ingeniously, he devised a method of submerging his boat beneath the surface using a rope and a stone‑set metal ring, rendering it invisible to coastal patrols.

In the early 18th century, Caesar joined the infamous Blackbeard’s crew as a lieutenant aboard the Queen Anne’s Revenge. After Blackbeard’s demise, Virginia authorities apprehended Caesar, sentencing him to death by hanging. To this day, treasure hunters scour Elliot Key, hoping to uncover the lost loot.

3 Henry Every

Henry Every, also known as “Long Ben” or “The King of Pirates,” orchestrated the most lucrative pirate raid ever recorded—equivalent to roughly $78 million today—before vanishing without a trace.

He began his maritime career in Britain’s Royal Navy, serving during the Nine Years’ War. After the conflict, he joined the merchant vessel Charles II, sailing to the West Indies to intercept French ships. A sluggish season left the crew restless, culminating in a mutiny that elevated Every to captain and rechristened the ship the Fancy.

Renowned for masterful ambush tactics and deft navigation, Every pillaged several English and Danish vessels before learning of a massive Indian convoy. He steered the Fancy toward the island of Perim, where he allied with pirate Thomas Tew and other local buccaneers to intercept the fleet of 25 Indian ships.

During the clash, Tew perished, and many pirate ships lagged behind. Undeterred, Every pursued the two largest ships, overtook them, and seized a treasure trove, allowing his crew to indulge in rampant rape, pillage, and torture. He then fled across the Atlantic, briefly anchoring near Nassau before setting sail for good.

After departing the Bahamas, Every, his crew, and the astounding loot disappeared, eluding the East India Company’s manhunt and cementing his legend as a phantom pirate.

2 Bartholomew Roberts

Bartholomew Roberts, famed as “Black Bart,” claimed over 400 vessels during his illustrious career, making him one of history’s most successful pirates. In 1719, while serving aboard the slave ship Princess, the vessel fell to a pirate attack off West Africa, and Roberts was swiftly drafted into the crew due to his exceptional navigational skills.

His ascent was rapid; after the captain perished in battle, Roberts was elected leader. Commanding the flagship Royal Fortune, he pursued and seized larger, better‑armed British, Portuguese, and Spanish warships with ruthless efficiency.

Roberts’ treatment of captives was chillingly pragmatic. After overtaking a slave ship carrying 80 chained Africans, he burned the vessel without freeing the prisoners. In a separate vendetta against the governor of Martinique, Roberts boarded a ship, murdered the governor, and displayed the corpse on the Royal Fortune’s yardarm for months.

His reign ended in the winter of 1722 when the English warship HMS Swallow caught up to him. In a daring confrontation, Roberts was mortally wounded by grapeshot to the throat. True to his wishes, his crew cast his body overboard, and despite exhaustive searches, his remains were never recovered.

Roberts’ legacy endures as a symbol of audacious piracy, his daring tactics and sheer audacity inspiring countless tales of high‑seas adventure.

1 Stenka Razin

Stenka Razin, a Cossack rebel and pirate of the mid‑1600s, remains a beloved folk hero throughout Russia. Historically, Cossacks enjoyed a degree of autonomy, but early 17th‑century policies tightened tsarist control, imposing harsh taxes and punishments.

Razin, a longtime community leader, was driven to vengeance after the execution of his brother by Russian troops. He rallied a force of 1,000 Don Cossacks, seized a fleet of tsarist ships, and began a campaign of plundering merchant vessels and liberating political prisoners along the Volga River.

His daring exploits elevated him to a peasant champion, inspiring uprisings across the Russian lands. As his army swelled beyond 2,000, Razin expanded his raids to the Caspian Sea and the Persian coast, cementing his reputation as a formidable maritime insurgent.

In 1671, Razin plotted a bold capture of Simbirsk but was betrayed by his own men. Captured and taken to Moscow, he endured four days of brutal torture before being executed. Despite his death, his legend persisted, with Cossack rebels continuing to resist Russian oppression, their stories and songs preserving Razin’s memory.

Alyssa Howard is a freelance writer and history fanatic. You can see her work at www.kitfoxsociety.wordpress.com.

During the Golden Age of Piracy (roughly 1650–1730), men under black flags were raiding and plundering ships across the Caribbean. We tend to picture them as ruthless marauders who terrorized European merchants, but the reality was far more nuanced. In fact, 10 ways pirates quietly reshaped the daily existence of African slaves, offering chances at liberty, equality, and even a voice on the high seas.

How 10 Ways Pirates Changed the Game for Enslaved Africans

1 Slavery Boomed When The Golden Age Of Piracy Ended

Pirates actually made a difference. The slave‑trade economy was crippled by pirate raids. Bringing slave ships to the New World became incredibly dangerous and costly, and pirate raids made life Hell for the slavers. According to Marcus Rediker, slavery in the New World didn’t have a chance until the pirates were gone.

The Golden Age of Piracy ended, according to some, when the pirate Black Bart died. Within ten years, slavery was booming, and England had more slaves than any other country in the Western world. Pirate raids on slavers and their ships were the one thing that held the slave trade back. Once they were out of the way, slavery came into full swing.

Pirates didn’t set out to make the world a better place—but in a strange way, they actually did.

2 Captured Pirates Were Sold Back Into Slavery

When an escaped African slave made it into a pirate crew, he had every reason to stay. Pirates gave them freedom and equality, and if they were separated from their brothers at sea, they’d find themselves back in chains.

One pirate on Samuel Bellamy’s crew was a black Miskito native named John Julian. On Bellamy’s ship, he was the pilot and one of the most important and respected people in the crew. When the ship crashed, though, all that changed. As soon as Julian was captured, he was sold into slavery, soon finding his way into the servitude of John Quincy, the grandfather of President John Quincy Adams.

Julian managed to escape and even killed a bounty hunter who was trying to catch him. In the end, though, he didn’t get away. The pilot was caught and executed because he refused to become a slave.

3 Sea Shanties Started Out As Slave Songs

All the sea shanties that we link to pirates should actually be linked with something else: black slaves. According to one theory, sea shanties never would have existed without the influence of African music.

Some scholars claim that parts of sea shanties seem to be borrowed from African songs. It’s more than just similar sounds; some of the earlier sea shanties actually use the pidgin language of early African slaves, suggesting that they might have been written by Africans or adapted from their music.

The multiracial crews on board of these ships, they believe, would have come up with sea shanties through collaboration. The Africans on board sang while they worked, and the white crew members heard them and started to adapt their songs into songs of their own.

4 Black Pirates Could Curse Out White People

The inherent racism that pervaded European culture in the 17th century doesn’t seem to have existed on pirate ships. Black crew members didn’t have to be polite or well‑mannered around their white crewmen. They could be as rude as they wanted.

One white sailor reported that after his ship was taken by the pirate Stede Bonnet, his crew was coerced into joining them. When he refused, a black pirate started cursing him out. He told the white sailor that he should be forced into slavery. The black man ended his tirade yelling, “You should be used as a negro!”

Stede Bonnet took the black pirate’s side. He heard the commotion, came over, and joined the black pirate in cursing the white man out. Then he did exactly what was suggested: He made the white man the black man’s slave.

5 Blackbeard’s Lieutenant Was An African Chieftain

Some black pirates rose up to high ranks and led crews of white men. One of them is legendary today: Black Caesar, the infamous pirate who ended up in Blackbeard’s crew.

Black Caesar was a chieftain in Africa until he was tricked and lured onto a slave ship. By chance, the slave ship was struck by a hurricane, and Black Caesar and a white crewman were the only ones to escape alive. Stranded at sea, the two men decided to lure in passing ships, rob them, and take them over. Soon, Black Caesar was leading his own pirate crew.

In time, he joined Blackbeard, but he kept a high rank. He was a lieutenant, one of the most important people on the ship. He was put in command of several white pirates, and Blackbeard trusted him with his life.

6 Pirates Gave Voting Right To Africans Centuries Before Civil Rights

Pirate captains weren’t dictators. The only time they had absolute command over their crew was during a raid. The rest of the time, the ship was run democratically, with every person on the ship free to have a voice in how it was run.

Captains were elected, and every member of the crew was given a vote. They would also draw up articles with strict rules on how to live together and how to punish offenders. This means that in the 17th century, there were free and equal African‑Americans voting for their leaders—but only on pirate ships.

7 Almost Every Pirate Ship Had Black Crewmen

The records we have of pirate crews show that almost every ship had at least a few black pirates in the crew. In most cases, black pirates made up more than just a couple of scattered crew members. They were a big presence on pirate ships. In fact, an estimated 25 to 30 percent of pirates were black.

In some ships, the rate was much higher. Many ships had a majority black crew, including some of the most famous and notorious pirates of all. Blackbeard, for example, had 60 black crew members on a ship of 100 men. Some crews were almost entirely black. One record describes a pirate ship with 50 men, only one of whom had white skin.

8 Pirates Freed Slaves

When a pirate crew captured a slave ship, they got a whole new crew. Often, they’d go into the lower decks, set the slaves free, and encourage them to join. This didn’t always happen. Some would just make the Africans slaves of their own, and some would do even worse. Black Bart, for example, once burned 80 slaves alive inside of a ship.

His cruelty, though, was an exception to the norm. Most pirates tried to avoid killing anyone if they could and didn’t bother trying to sell human cargo. Pirates were criminals, and it was difficult and dangerous for a criminal to sell to a slave trader, so they often just let the African slaves join their crew.

Escaped slaves would become pirates, too. In the early days of slavery, many slaves escaped. Some joined the maroons, which were communities of escaped slaves who survived by hiding in the mountains. Others, though, would meet up with pirate crews instead and join life on the sea.

9 Pirates Targeted Slave Ships

Pirates didn’t just attack any ship they saw. When they raided a ship, it was to make a profit, so they picked ones that were worth their while. No type of ship, though, was a bigger target for pirates than slave ships.

The pirates weren’t particularly concerned about African rights; they just wanted the ships. Slave ships were extremely useful for a pirate crew. They were usually fast as well as large, which gave them a lot of space to keep and feed their crew.

The most famous pirate ships in history were captured slave ships. Blackbeard’s Queen Anne’s Revenge and Samuel Bellamy’s Whydah were both stolen from slavers and turned into feared pirate vessels.

10 The First Buccaneers Were Escaped Slaves

When we think of pirates in the Caribbean, white faces usually come to mind. We picture people like Blackbeard or Samuel Bellamy—Europeans buccaneers who raided other white men. The first buccaneers in recorded history, though, had dark skin. The record in question is the journal of a French sailor who, on the coast of Hispaniola, met two men he describes as “a mulatto and a negro.”

The men told him that they sustained themselves by poaching livestock. This wasn’t a confession of shameful sins; the men were making a sales pitch. Sailors’ lives were hard, and they were trying to recruit him and his sailors to join them in their pirating lives.

It worked. By the time the Frenchman returned to his ship, six of his crew had disappeared. His white crew had abandoned him, leaving the ship to serve under two black pirates.

From the swashbuckling chaos of Disney’s Pirates of the Caribbean to the classic adventures of Treasure Island, the silver screen has fed us a steady diet of pirate mythos. Yet the movies love to sprinkle in a generous helping of creative license, turning history into high‑seas fantasy. Below are the top 10 ways Hollywood tricks you about pirates, exposing the myths that have set sail far from the real‑world reality.

The Top 10 Ways Films Distort Pirate Lore

10 Pirates Were Criminals

When most people picture a pirate, they imagine a seafaring thief who robs ships for treasure. That broad definition does cover a wide range of sea‑based plundering, from Viking coastal raids to modern Somali hijackings. However, the popular image zeroes in on the Caribbean marauders who roamed between 1650 and 1720 – the era historians call the Golden Age of Piracy. Disney’s Pirates of the Caribbean saga is set right at the tail end of that period.

What many overlook is that a form of “legal” piracy also existed. Anyone who could muster a vessel – or secure a loan to do so – could petition their government for a Letter of Marque. This document acted as a piracy licence, authorising private ship owners to seize enemy vessels on behalf of the crown. At the time, Spain ferried massive loads of gold and silver across the Caribbean, and both France and Britain were eager to tap that wealth. They happily issued letters of marque, demanding only a cut of the loot for the state.

Historians generally agree that the Golden Age fizzled out when Spain curtailed its treasure convoys, prompting France and Britain to stop issuing privateering commissions. Without the legal cover, governments turned their guns on the outlawed pirates who had become a nuisance to colonial interests, rounding them up and ending the era.

9 Pirates Are Noble Anti‑Heroes

Hollywood loves to paint pirates as reluctant, almost romantic anti‑heroes, and Jack Sparrow’s hesitant swagger isn’t entirely fictional. In reality, pirates were mindful of preserving their vessels and crews – ships were expensive, and crews were valuable assets. Their preferred strategy was to scare a target into surrendering without a single shot, minimizing damage to both ship and crew.

When intimidation was required, pirates could be brutally ruthless. Contemporary accounts describe horrific tactics: victims were sometimes bound by the arms and hung, beaten with cutlasses, had fingers severed one by one, or even had burning matches forced into their eyes. Such terror ensured that most merchant captains chose to hand over their riches rather than face the gruesome alternative.

While modern movies often depict pirates as flamboyant villains, the reality was that they were far more terrifying. Their reputation for savage vengeance was a calculated tool that forced many ships to capitulate before a single cannon roared, making piracy a business of psychological warfare as much as firepower.

8 Pirates Said “Argh” and “Shiver Me Timbers”

Contrary to popular belief, historic pirates didn’t have a signature slang. They were ordinary seafarers, often former merchant sailors, who spoke in the everyday vernacular of the day. Crafting a unique pirate patois would have been a liability, instantly flagging them to naval authorities and bounty hunters.

The iconic exclamations “argh!” and “shiver me timbers” are products of 20th‑century dramatization. The first notable contribution came from Lionel Barrymore, who added a gravelly “arrgh” to his 1934 portrayal of Billy Bones in Treasure Island. Later, English actor Robert Newton, with his West Country accent, popularized the exaggerated pirate drawl while playing Long John Silver in the 1950 film adaptation, cementing the phrases in the public imagination.

These stylized utterances became so entrenched that September 19th was later declared International Talk Like a Pirate Day, chosen because it coincided with the birthday of one of the holiday’s creators’ ex‑wives. The day celebrates the whimsical, invented lexicon rather than any historical reality.

7 Pirates Buried Their Treasure

In truth, real‑world pirates rarely buried loot. Once a ship was seized, the spoils – whether gold, silver, silks, cocoa, or spices – were swiftly divided among the crew according to rank. Pirates lived for the moment; they didn’t build savings accounts or 401(k)s. The perilous nature of their trade meant they spent their share almost immediately.

There are a few notable exceptions. Sir Francis Drake, the famed English privateer, reportedly buried tons of gold and silver along Panama’s coast to keep it from Spanish hands, only to retrieve it later. Captain William Kidd famously hid a cache on Long Island while evading the British Crown, but he was captured before he could recover it; the buried treasure was later used as evidence against him. These rare cases have fueled centuries‑long treasure‑hunting legends.

Equally mythical is the notion of the classic “X marks the spot” treasure map. Such maps would have been a glaring liability, providing a clear guide for anyone to locate the hidden riches. The idea was popularized by novelists and film adaptations of Treasure Island, cementing the image of a parchment with a conspicuous X.

6 Pirates Gave “The Black Spot”

The ominous “Black Spot” is a literary invention by Robert Louis Stevenson for his 1883 novel Treasure Island. In the story, a piece of paper with a darkened circle signals a pirate’s judgment – often a death sentence or a removal from command.

Hollywood has repurposed the motif in various ways. In Pirates of the Caribbean: Dead Man’s Chest, the Black Spot becomes a physical boil that marks those indebted to Davy Jones, prompting the Kraken to hunt them down. A similar concept appears in a pirate‑themed episode of Doctor Who, where the spot serves as a foreboding warning.

Historical records, however, show no evidence that real pirates ever used a symbolic black spot to convey verdicts. When a crew wanted to depose a captain, they simply did so – no parchment, no theatrical suspense. The Black Spot remains a dramatic flourish born of fiction, not a factual practice.

5 Pirates Walked the Plank

The first literary mention of a victim being forced to walk a plank appeared in Daniel Defoe’s 1724 work A General History of Pirates. Defoe described pirates tossing a captive over the side and telling them they could swim to safety if they wished. This dramatic image captured imaginations and quickly entered popular culture.

Subsequent works – from Robert Louis Stevenson’s Treasure Island to J.M. Barrie’s Peter Pan, Monty Python’s sketches, the Pirates of the Caribbean series, and even Star Wars: Return of the Jedi – all featured the plank as a signature punishment. Yet historians have found no concrete evidence that pirates actually forced enemies to walk a plank. They did employ brutal punishments like flogging, marooning (abandoning a person on a deserted island), or outright murder. When drowning was desired, they simply pushed the victim overboard without the theatricality of a wooden plank.

The earliest documented reference to a “plank” scenario actually stems from a surgeon’s mate testifying before the British House of Commons, describing slave‑ship officers debating whether to make enslaved people walk the plank to conserve provisions. This illustrates that the trope originated outside of pirate conduct and was later co‑opted into pirate lore.

4 Pirates Wore Eyepatches

Historical evidence for eyepatches among pirates is scant. The only documented pirate known to wear one was Rahmah ibn Jabir al‑Jalahimah, a notorious Gulf pirate who lost an eye in combat. Beyond that singular case, there’s little to suggest that eyepatches were a common accessory among Caribbean buccaneers.

One popular theory posits that pirates used eyepatches to keep one eye dark‑adapted for sudden moves below deck, where lighting could be dim. Since the human eye takes roughly 25 minutes to adjust from bright sunlight to darkness, having a permanently shaded eye could confer a tactical edge when boarding a darkened vessel. The TV show MythBusters gave this hypothesis a “plausible” rating.

The notion appears to have originated in the 1930s when the U.S. Navy explored the concept for military use. A 1939 Navy handbook noted that “dark adaptation in one eye is independent of the other” and suggested a patch could be advantageous. A 1934 text even referred to it as a “pirate’s patch.” While intriguing, the idea never became a documented pirate practice.

3 Pirates Flew “The Jolly Roger”

The iconic black flag bearing a skull and crossbones – the “Jolly Roger” – is instantly associated with piracy. Historically, this design was flown by notorious captains such as “Black Sam” Bellamy, Edward England, and Edward “Blackbeard” Teach. However, there was no universal standard; each crew could customize its banner with personal symbols.

Some pirates opted for elaborate designs: full‑bodied skeletons, hourglasses to remind victims of dwindling time, or scenes of a sword‑wielding figure stabbing a heart. Walter Kennedy, for instance, combined a skull and crossbones with a naked man brandishing a sword beside an hourglass, creating a uniquely menacing emblem.

Pirates typically hoisted their flags only when they were close enough to a target ship to induce panic. By revealing the dreaded banner at the last moment, they maximized the chance of a swift surrender, securing treasure without a protracted battle. The dramatic, ever‑present flag in films is a cinematic convenience rather than a constant visual reality.

2 Pirate Ships Were Enormous

The stereotypical image of a pirate vessel is a massive, three‑masted galleon bristling with rows of cannons. While such ships were indeed the pride of royal navies, real pirates shunned them. Galleons were deep‑draft, cumbersome, and ill‑suited for quick get‑aways or shallow‑water maneuvers.

Instead, most pirate crews favored nimble, single‑masted sloops that could dart in and out of coves, navigate shallow reefs, and vanish before a naval pursuit could close in. These smaller vessels offered speed, agility, and the element of surprise – essential traits for outlawed seafarers.

The reason audiences rarely see these sleek sloops is practical: larger ships provide a more impressive visual canvas for filmmakers, accommodate extensive camera rigs, and allow actors space to perform dramatic scenes. Consequently, Hollywood opts for the grandiose galleon, reinforcing the myth of oversized pirate warships.

1 Pirates Were White

While modern blockbusters like the recent Pirates of the Caribbean installments have begun to diversify their casts, the long history of pirate cinema has overwhelmingly depicted pirates as white Europeans. Classic adaptations of Treasure Island and Peter Pan largely ignored the multicultural reality of 17th‑ and 18th‑century piracy.

In truth, pirate crews were often racially mixed. They frequently raided slave ships, sometimes offering enslaved individuals freedom in exchange for joining the crew. On several vessels, freed slaves comprised a significant portion of the crew – in some cases, over a quarter of the men on board were former slaves.

Pirate ships also provided rare opportunities for people of color to attain positions of authority. Captain William Kidd employed a black quartermaster, and the infamous Blackbeard commanded a crew that included many Black sailors. As seafarers, pirates were a melting pot of nationalities and backgrounds, forging a unique, inclusive community on the high seas.