The Real Pirates of the Caribbean

The Real Pirates of the Caribbean

Khalid Elhassan - January 7, 2020

Pirates, especially those who plied their trade during the Golden Age of Piracy in the seventeenth and eighteenth centuries, are often seen as romantic anti-heroes. Real piracy was seldom glamorous or romantic. Pirates’ careers were typically violent, brutish, and short, their lives ended by battle, the hangman’s noose, or more often, by any of a slew of diseases and illnesses.

Relatively few pirates ever seized enough treasure upon which to retire. Of those few, the fewer yet who lived long enough to leave piracy had already blown their loot on drink, women, or were swindled out of it, by the time they called it quits, and ended their days in poverty. Still, the lives of many pirates were fascinating, so following are forty things about history’s real pirates of the Caribbean.

The Real Pirates of the Caribbean
Montbars the Exterminator. Pintrest

40. Montbars the Exterminator

Seventeenth-century French buccaneer Daniel Montbars (1645 – disappeared 1707), better known as Montbars the Exterminator, earned his nickname and then some. One of the most feared pirates of his era, Montbars became known as the Exterminator because of the sheer bloody-mindedness and glee he displayed in killing Spaniards.

Born into a wealthy family, Montbars was raised and educated in France as a gentleman. In childhood, he developed a hatred of Spain and all things Spanish, based on what he read of the cruelties of the Conquistadors towards the New World natives. In 1667, he joined his uncle in the French Royal Navy, and accompanied him to the Caribbean. There, Montbars’ anti-Spanish sentiment grew in leaps and bounds when his ship was sunk in a battle against Spaniards, during which his uncle was killed.

The Real Pirates of the Caribbean
Montbars the Exterminator. Metropolitan Museum of Art

39. The Exterminator’s Turn to Piracy

After his uncle’s death, Montbars left the French Navy and headed to the pirate haven of Tortuga, an Island off the Haitian coast. Between his professional expertise as a naval officer, and his seething hatred of Spain, the buccaneers’ main foe, he was welcomed with the open arms. Before long, he was captaining his own buccaneer ship.

He made a name for himself in early action against a Spanish vessel: “Montbars led the way to the decks of the enemy, where he carried injury and death; and when submission terminated the contest, his only pleasure seemed to be to contemplate, not the treasures of the vessel, but the number of dead and dying Spaniards, against whom he had vowed a deep and eternal hatred, which he maintained the whole of his life“.

The Real Pirates of the Caribbean
Buccaneers extorting tribute from a captured city. Military Wiki

38. Rampaging Throughout the Caribbean

Montbars went on a piratical rampage against the Spanish Main – Spain’s possessions in the Caribbean, the Gulf of Mexico, and the coastal mainland from Florida to Venezuela. He raided Spanish settlements in Cuba, Puerto Rico, and Mexico. On the Venezuelan coast, he sacked and burned the towns of Maricaibo, San Pedro, Porto Caballo, and Gibraltar, among numerous other settlements and forts.

It was during this rampage that Montbars became known as the Exterminator. He gave no quarter, and tortured captured Spanish soldiers. Among his more infamous tortures was opening a victim’s abdomen, pulling out a gut and nailing it to post, then forcing the victim to “dance to his death by beating his backside with a burning log“. He and his crew amassed a fortune, which they reportedly buried near Grand Saline, Texas. However, the Exterminator never came back to retrieve it: he vanished in 1707, most likely lost at sea.

The Real Pirates of the Caribbean
Jean-Francois Roberval. Pintrest

37. From Courtier to Pirate

Jean-Francois Roberval (1500 – 1560) was a French nobleman, adventurer, and pirate, who began his career in the French army in Italy. There, he met and befriended France’s crown prince, the future King Francis I, who became Roberval’s lifelong pal, and frequent guest and hunting companion on the Roberval estates.

Moving into high society, hosting royalty, and living as a courtier was pretty expensive though, and it eventually drove Roberval deep into debt. In 1541, Francis I commissioned Roberval to establish a settlement of about 500 French colonists in Canada. However, the king did not furnish his friend with sufficient funds, so to make ends meet, Roberval turned to piracy to help finance the settlement.

The Real Pirates of the Caribbean
Sixteenth-century French naval action. Wikimedia

36. Piracy in a Good Cause?

To help sustain the recently established French settlement in Canada, Jean-Francois Roberval became a pirate, preying upon English merchant ships. His friend and patron King Francis I enjoyed tweaking the English, but to avert open hostilities with England, he rebuked Roberval. It amounted to a wink-wink-nudge-nudge slap on the wrist, and Roberval continued plundering English ships.

The Canadian settlement eventually failed, and the survivors were repatriated back to France. Roberval remained in the New World, however, and continued his career, now focusing on Spanish ships and possessions in the Caribbean. Throughout much of the 1540s, he terrorized the Spaniards, attacking Cartagena, Rancheras, and Santa Marta in Colombia, plus Baracoa and Havana in Cuba. Roberval finally retired from piracy in 1547 and returned to France, where he converted to Protestantism. He got tangled up in France’s Wars of Religion, and was assassinated in Paris in 1560.

The Real Pirates of the Caribbean
Michel de Grammont. Wikimedia

35. A Duel Leads to a Career in Piracy

When Michel de Grammont was born into a French noble family in 1650, few would have expected that the aristocratic baby would end his days as an infamous pirate. Yet that was to be the destiny of de Grammont, who terrorized the Caribbean and the Gulf of Mexico for a decade and a half.

That radical transformation began when a fourteen-year-old de Grammont was angered by a French army officer who was courting his sister, and challenged him to a duel. Despite his youth, he won the duel and killed the officer. That got de Grammont into trouble, and he was forced to flee France. He ended up in Hispaniola, and became a privateer – a pirate operating with a “Letter of Marque” from a government, authorizing him to prey upon enemy shipping in time of war.

The Real Pirates of the Caribbean
Michel de Grammont. Wikiwand

34. A Spectacular Start

De Grammont’s career as a privateering captain got off to a spectacular start, when he captured a Dutch fleet that included a ship known as The Purse of Amsterdam for the precious cargo it carried. It netted him 400,000 livres, the equivalent of about U$4 million today. News of that success spread, and before long, de Grammont was commanding his own pirate fleet. He kept his men busy, attacking Dutch and Spanish shipping and possessions.

One of his most daring exploits was a successful raid on Cumana in Venezuela in 1680, despite great odds: he had only 50 men, while the defenders had 2000 soldiers and 17 ships with 328 cannons. In 1683, he sacked Veracruz, Mexico, and took 4000 prisoners for ransom. De Grammont’s depredations finally ended in 1686, when his ship was caught in a storm, and went down with all hands.

The Real Pirates of the Caribbean
Queen Elizabeth I knighting Sir Francis Drake aboard his ship, The Golden Hind. Dissolve

33. Queen Elizabeth’s Favorite Pirate

Sir Francis Drake (circa 1540 – 1596) was Queen Elizabeth I’s favorite pirate, and for good reason. The Virgin Queen invested in English pirates like modern venture capitalists invest in Silicon Valley startups, and she made out like a bandit from the returns on Drake’s high seas high jinks and predations.

The most celebrated seaman of the Elizabethan Era, Drake led one of history’s most adventurous seafaring careers. He became the greatest pirate of his day, preying upon Spanish shipping and coastal settlements. He also became the second man to circumnavigate the globe after Magellan’s expedition, during which endeavor he combined exploration with opportunistic plunder. He further cemented his place in history by playing a prominent role in defeating the 1588 Spanish Armada.

The Real Pirates of the Caribbean
Sir Francis Drake. Biography

32. An early Start in Piracy

Francis Drake first went to sea at an early age. As a teenager, he was enlisted by his relatives, the Hawkinses, a clan of privateers who preyed upon French coastal shipping. By the 1560s, Drake had risen to command his own ship and entered the slave trade, smuggling shackled captives illegally into Spain’s New World possession.

During one such trip, Drake was cornered by Spanish authorities, and escaped only with heavy loss of life among his crew. The experience left him with a lifelong hatred of Spain. In 1572, he received a Letter of Marque from Queen Elizabeth, authorizing him to plunder Spanish property. Armed with that authorization, Drake raided Panama, but was wounded and forced to retreat. After recovering, he raided Spanish settlements around the Caribbean, and returned to England in 1573 with a rich haul of gold and silver.

The Real Pirates of the Caribbean
A replica of Francis Drake’s ship, The Golden Hind. Wikimedia

31. The First Pirate to Circumnavigate the Globe

In 1577, Francis Drake led an expedition of 5 ships to raid the Pacific coast of Spanish South America, which was wholly undefended in those days. Braving storms, he passed through the Straits of Magellan in his flagship, the Golden Hind, then sailed up the coasts of Chile and Peru. Near Lima, he captured a Spanish ship which yielded 25,000 gold coins, and soon thereafter captured a fabulously rich prize, the Cacafuego, a Manilla galleon which yielded a treasure of 80 pounds of gold, 13 chests of coins, and 26 tons of silver.

The Real Pirates of the Caribbean
Drake’s circumnavigation of the globe. World Topography

With his holds full of loot, Drake crossed the Pacific, sailed the Indian Ocean, rounded the tip of Africa, and returned to England on September 26th, 1580, having circumnavigated the globe. It was a first for a pirate, and only the second time anybody had accomplished that feat since Ferdinand Magellan’s expedition, over half a century earlier.

The Real Pirates of the Caribbean
Drake during the attack on Cadiz that Singed the King of Spain’s Beard. Historic UK

30. Singeing the King of Spain’s Beard

In 1585, Francis Drake was put in charge of a fleet which harried Spanish shipping, captured Santiago in the Cape Verde Islands, and plundered Spanish settlements in Florida and Hispaniola. In 1587, with King Philip II of Spain threatening to invade England, Drake led daring preemptive raids against Spanish fleets assembling in Cadiz and Coruna for an invasion of England. He inflicted significant damage, which prevented the Spaniards from sailing that year. As contemporaries described it, Drake had “Singed the King of Spain’s Beard“.

The following year, the combined Spanish fleet, the famous Armada, set sail. Drake played a leading role in its dispersal and eventual destruction. Particularly on the night of July 29th, 1588, when he organized fire ships against the Armada assembled in Calais, forcing its ships out of that port and into the open sea. There, they were scattered by a combination of English warships and adverse weather.

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Drake’s burial at sea off Portobelo. Wikimedia

29. Pirate or Privateer?

Sir Francis Drake’s eventful life finally came to an end in 1596. After a series of failed raids and attacks against Spanish America, he caught dysentery while anchored off Portobelo, in Panama, and died.

His career, with its turns from soldier and sailor to outright pirate, illustrates the era’s murky lines between outright piracy and legalized piracy, also known as privateering. In the years to come, the difference between a pirate liable for the hangman’s noose, and a privateer likely to receive official acclaim and adulation, was no more than a piece of paper. Those plundering the seas while wielding Letters of Marque were lionized, while those doing the same without such a fig of legality were condemned as pirates.

The Real Pirates of the Caribbean
The Captain Morgan brand. Licorea

28. The Real Captain Morgan

Sir Henry Morgan (1635 – 1688), familiar to many as the swashbuckling figure gracing bottles of Captain Morgan’s Rum, was one of history’s most successful pirates. A Welsh privateer who operated out of Port Royal, Jamaica, Morgan plundered and terrorized the Spanish Main and Spain’s Caribbean possessions in the 17th century. He grew rich off the plunder, went on to become Lieutenant Governor of Jamaica, and retired to the life of a wealthy plantation owner.

Morgan first arrived in the Caribbean with a British expedition that seized Jamaica in 1655. By 1666, he was second in command of a fleet of buccaneers operating against Dutch colonies during the Second Anglo-Dutch War. A year later, Morgan was the buccaneers’ top commander, and he led them in capturing Puerto Principe in Cuba, and in storming and sacking the wealthy and well-fortified city of Portobelo in Panama.

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Morgan’s attack on Portobelo. Wikimedia

27. From Pirate to Lieutenant Governor

In 1669, Henry Morgan pillaged the wealthy Spanish settlements around Lake Maracaibo in Venezuela. In 1671, he mounted his most daring and ambitious expedition, when he led a fleet of 36 ships and 2000 pirates against Panama City. Landing on Panama’s Caribbean coast, Morgan led his men across the isthmus and through thick jungles to attack and seize the city on the Pacific coast.

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Henry Morgan. Pintrest

However, England had signed a peace treaty with Spain by then. To appease the livid Spanish, Morgan was arrested and sent to London for appearances’ sake, but upon arrival, he was lionized and treated as a hero. In 1674, he was knighted by King Charles II and sent to Jamaica as its Lieutenant Governor. There Morgan remained, a wealthy plantation owner and powerful political figure, occasionally subbing in as governor during that officeholder’s absence, until his death in 1688.

The Real Pirates of the Caribbean
Francois L’Olonnais. Facsimilium

26. The Flail of Spain

Francois L’Olonnais (1630 – 1669), birth name Jean-David Nau, was one of history’s most feared pirates, with a reputation for brutality that stood out in age and within a profession where brutality was the norm. He had a particular bone to pick with the Spanish, and his relentless pursuit of that vendetta earned him the nickname “The Flail of Spain“.

L’Olonnais was born in dire poverty in France – so dire that his family sold him into indentured servitude as a child. It was in that capacity that he arrived in the Caribbean at age fifteen, and spent the next ten years of his life toiling on Spanish plantations, performing back-breaking menial work in harsh conditions. He endured mistreatment and sundry humiliations, and by the end of his term of indentured servitude in 1660, L’Olonnais had developed a burning hatred of Spain and all things Spanish.

The Real Pirates of the Caribbean
A Tortuga buccaneer. Wikimedia

25. The Tortuga Privateer

At the end of his term of indentured servitude, Francois L’Olonnais moved to Tortuga, a French island north of modern Haiti that was a nest of piracy and lawlessness at the time, and joined its buccaneers. He quickly impressed, and within a short time, Tortuga’s French governor gave L’Olonnais his own ship, a Letter of Marque authorizing him to prey on Spanish vessels as a privateer, and turned him loose.

In going about his legalized piracy, L’Olonnais set himself apart with a reputation for viciousness and ferocious cruelty in the treatment of prisoners, particularly Spanish ones. An expert torturer, L’Olonnais reveled in slicing off strips of his victims’ flesh, burning them, or tightening ropes around their skulls until their eyeballs popped out of their sockets.

The Real Pirates of the Caribbean
Francois L’Olonnais and his men indulged in an orgy of atrocities when they captured Maracaibo. Awesome Stories

24. Hiding in Blood and Guts

Early in his career, Francois L’Olonnais was shipwrecked off Yucatan. Most of the crew survived to reach shore, only for all of them to get killed soon thereafter when Spanish soldiers found and fell upon them. L’Olonnais survived by covering himself in blood and viscera, and hiding among the dead. Later, he snuck into a nearby town which was celebrating the killing of the pirates, and arranged for an escape back to Tortuga.

He resumed his depredations against Spain, and in 1666 assembled a fleet of 8 ships and 440 pirates to attack Maracaibo in modern Venezuela. En route, he came across and looted a Spanish treasure ship, which yielded 260,000 Spanish dollars, in addition to gemstones and cocoa beans. It was a prelude to the most monstrous act of his career.

The Real Pirates of the Caribbean
The death of Francois L’Olonnais. Metropolitan Museum of Art

23. The Monster of Maracaibo Gets Eaten by Cannibals

Upon his arrival at Maracaibo with a pirate fleet, Francois L’Olonnais discovered that the citizens had fled. So he plunged into the surrounding jungle after them, tracked them down, and tortured them into revealing where they had hidden their valuables. He and his men then spent two months in an orgy of widespread rape, pillage, and murder. They finally put the town to the torch and tore down its fortifications before leaving.

The following year, L’Olonnais led an even bigger pirate expedition against Central America, only for his men to get ambushed and massacred in Honduras. He was one of the few survivors who managed to escape back to a ship, but it ran aground off the coast of Panama. Disembarking, L’Olonnais led his men inland in search of food, only to get captured, killed, and eaten by an indigenous tribe.

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Artistic impression of Henry Avery. Villains Wiki

22. The Pirate Who Got Away

Real-life piracy was often a short career that ended in death at a young age from disease or violence. Relatively few major pirates got to retire with their loot, but still – some did. One such was Henry “Long Ben” Avery (circa 1655 – ­disappeared 1699).

Avery not only pulled off one of history’s most lucrative piratical heists, but also avoided getting killed in battle or an arrest and execution, and reportedly lived to retire with his plunder. His life inspired a popular play, The Successful Pyrate, about a pirate who retires after one year of piracy, and lives the rest of his life under an assumed name as a rich man.

The Real Pirates of the Caribbean
Henry Avery loading treasure from the captured Ganj-i-Sawai into his hold. Royal Museums Greenwich

21. The Young Mutineer

Henry Avery was born in Plymouth, England, and went to sea at an early age. By 1694, he had risen in rank to become First Mate in the Charles II, a privateer serving the king of Spain. It was in that capacity that he led the disgruntled crew in a mutiny that seized the ship. Renaming the vessel the Fancy, the now-captain Avery issued a proclamation that English ships had nothing to fear from him. He then fell upon foreign vessels as he sailed into the Indian Ocean.

Avery arrived in Madagascar in 1695, where he had the Fancy refitted and modified for speed. Then, after seizing a French ship and convincing 40 of its crew to join him, he sailed north to intercept the Indian Mughal fleet as it returned from the annual pilgrimage to Mecca. In cooperation with 5 other pirate ships, Avery intercepted the Mughal fleet and captured a ship whose holds yielded about £60,000 – a sizeable haul in those days. He was just getting started.

The Real Pirates of the Caribbean
Henry Avery entering the quarters of the Mughal Emperor’s daughters, who was captured along with the Ganj-i-Sawai. Wikimedia

20. Piracy’s Greatest Heist

Capturing £60,000 from Mughal ship only whetted the appetite of Henry Avery and his crew. Soon as they secured that bit of loot, they resumed their chase of the Mughal fleet, and caught up with its flagship, the Ganj-i-Sawai – a formidable vessel, sporting 62 guns and carrying 500 musket men.

After an hours-long ferocious fight, during which the Mughal captain panicked and fled to hide below decks among concubines, the Pirates prevailed. After securing the vessel, Avery and his crew went on a days-long orgy of rape and torture. The loot from the Ganj-i-Sawai came to about £600,000 pounds in gold, silver, precious metals and goods. It was the largest single haul ever scored by a pirate.

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Henry Avery selling his jewels. Pintrest

19. The Great Double Cross

Seizing the Ganj-i-Sawai was a great coup, but Henry Avery did not want to share its loot with the other pirate ships that had participated in its capture. So Avery and his men tricked them. They loaded Fancy’s hold with the £600,000 worth of loot seized from the Mughal ship, and made arrangements with the other pirate ships to meet and divide the bounty. Then they took off. The Fancy, recently modified for speed, soon out-sailed the other pirate ships, who followed in her wake in impotent rage, until she disappeared below the horizon.

The Fancy made it to the Caribbean, and after the loot was divided, the crew split up and Avery disappeared from history. It is commonly assumed that he established a new identity somewhere and lived his remaining days in great wealth. However, some sources claim that he returned to England, only to get swindled out of his riches, and end his days an impoverished pauper.

The Real Pirates of the Caribbean
Black Bart. ThoughtCo

18. Black Bart, the Reluctant Pirate

Bartholomew “Black Bart” Roberts (1682 – 1722) is considered to be one of the most successful pirates of the Caribbean. He captured and looted more ships during his career than his contemporaries Black Beard, Jack Rackham, Francis Sprigg, and Edward Low put together. His spectacular success as a pirate was ironic, because he had never wanted to be a pirate to begin with.

In 1719, Black Bart had been an officer aboard a slaver that was captured by pirates, who forced him to join them. Within six weeks, he had impressed his new crew mates so much that when their captain was killed, the pirates elected Bart their new captain. He soon got over any doubts he might have had about his new career, and took to piracy with a will.

The Real Pirates of the Caribbean
Black Bart. Royal Museums Greenwich

17. A Spectacular Start

Few pirates ever got started with as big a bang as that of Black Bart. He kicked off his career as a pirate captain by sailing to South America, where he came upon a Portuguese treasure fleet assembling in a bay in northern Brazil. Pretending to be one of the convoy, Black Bart slipped into the fleet, a wolf in sheep’s clothing. That night, he quietly seized one ship, forced its captain to point out the fleet’s richest vessel, then captured it and fled before the escorting Portuguese warships realized what was happening under their noses.

The loot came to over 40,000 gold pieces, plus jewelry commissioned for the king of Portugal. That daring deed to start off his piratical career struck a chord and made Black Bart famous. Sailing north into the Caribbean, pirates flocked to his side, and he put them to good use.

The Real Pirates of the Caribbean
Black Bart’s flag, showing him and death holding an hourglass. Pintrest

16. Black Bart Runs Up the Score

At the height of his career, Black Bart commanded a fleet of four pirate ships and over 500 pirates. Much of his success is owed to his organizational and leadership abilities, combined with charisma and daring that inspired and encouraged his crews. During his four-year career as a pirate, he captured and looted over 470 ships.

The Real Pirates of the Caribbean
Black Bart trying deserters. Metropolitan Museum of Art

He was cruel and sadistic, and relied on terror and a frightening reputation to win compliance. In 1722, he captured a slave ship at anchor while her captain was ashore, and sent him a message demanding ransom for the return of his ship. When the captain refused, Roberts burned the ship, with 80 slaves shackled aboard. A bloodthirsty man, his end was appropriately bloody: in 1722, Black Bart decided to fight it out with a Royal Navy vessel, only to get his throat torn out by grapeshot in the first broadside. His men honored his standing order that he be buried at sea, and immediately weighed him down and threw him overboard before surrendering.

The Real Pirates of the Caribbean
Calico Jack. Wikimedia

15. Fame and Success Did Not Always Go Hand in Hand in the Golden Age of Piracy

Calico Jack, real name John Rackham (1682 – 1720), is one of the best-known pirates of the Golden Age of Piracy, but not because he was particularly successful or much good at being a pirate. Compared to other famous pirates, Calico Jack’s career was middling, and his accomplishments mediocre.

He nonetheless became famous because of his associations with other, more successful pirates. Also, because of his venality and backstabbing, that stood out even in a profession built on venality and backstabbing. His first mate also designed the Jolly Roger flag, so there was that. Most important of all, Calico Jack became famous because his crew included two female pirates, Anne Bonny and Mary Read.

The Real Pirates of the Caribbean
Anne Bonny, Calico Jack, and Mary Read. Magnolia Box

14. Becoming Calico Jack

John Rackham was nicknamed Calico Jack because of the colorful calico clothes he favored. In 1718, he was quartermaster aboard the pirate sloop Ranger, when she encountered a French warship twice her size. The pirate captain, choosing discretion over valor, fled. The pirate crew decried what they viewed as cowardice, voted the captain out of the command, and replaced him with Calico Jack.

As captain, Calico Jack specialized in plundering small vessels engaged in coastal trade, but fell upon larger ships when the opportunity presented itself. In 1719, he accepted a royal pardon, renounced piracy, and accepted a commission from the governor of the Bahamas to hunt pirates. However, a love triangle involving Anne Bonny, the future pirate, grew complicated, and ended with the lovers stealing a sloop to slip out of the Bahamas. That voided Calico Jack’s recent pardon.

The Real Pirates of the Caribbean
Bronze statue in the Bahamas of Anne Bonny and Mary Read. Pintrest

13. “If You Had Fought Like a Man, You Would Not Hang Now Like a Dog!”

In October of 1720, Calico Jack and most of his crew were at anchor and drunk out of their gourds, when a pirate hunter chanced upon their ship. The men were too inebriated to defend themselves, so the only fight was put up by the crew’s two women, Anne Bonny and Mary Read, who offered fierce resistance before they were finally subdued. Captured, Calico Jack was tried and convicted of piracy, and sentenced to death by hanging.

His lover, spared the noose after “pleading her belly” – she was pregnant, and the law did not permit hanging pregnant women – had little sympathy for him. When he grew maudlin while bidding her goodbye before his execution, Anne Bonny reportedly sneered: “if you had fought like a man, you would not hang now like a dog!” John Rackham, AKA Calico Jack, was hanged on November 18th, 1720, and his corpse was displayed from a gibbet at the entrance to Port Royal, Jamaica, in an inlet known thereafter as Rackham’s Cay.

The Real Pirates of the Caribbean
Black Sam Bellamy. Crime Museum

12. Black Sam’s Turn From Treasure Hunter to Pirate

Captain Black Sam Bellamy, real name Samuel Bellamy (1689 – 1717), did not earn the nickname “Black Sam” because of any fell acts or dark deeds. He simply got called that because he eschewed the white powdered wigs of his era, and grew out his own mane of long black hair instead. He went to sea at an early age, and by the time he reached adulthood, he was a seasoned Royal Navy combat veteran, with a number of sea battles under his belt.

In 1715, Black Sam went to Cape Cod in search of relatives, and there, news arrived of the wreck of a Spanish treasure fleet in a storm off the Florida coast. Bellamy joined a treasure hunting expedition that hoped to recover the sunken riches, but when they failed to do so, they turned to piracy to recoup their investment.

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Black Sam Bellamy’s flag. Wikimedia

11. Joining Piracy’s Big Names

Early in his piratical career, Black Sam Bellamy fell in with captain Benjamin Hornigold and his first mate Blackbeard of the Marianne. In 1716, Hornigold’s refusal to attack English ships led his crew to vote him out as captain, and kick him and Blackbeard off the ship. Bellamy, who had none of Hornigold’s compunctions about preying on English vessels, was elected captain in his stead.

Black Sam’s biggest haul was the Whydah Gally, which he overtook on its maiden voyage after a three day chase, and captured it with a rich haul of gold, ivory, indigo, and other high value goods. Upgrading the Whydah Gally with extra cannon and turning it into his flagship, Bellamy then fell upon the shipping lanes to the Carolinas and New England, and feasted.

The Real Pirates of the Caribbean
Treasure trove recovered from the wreck of the Whydah Gally. Wikimedia

10. Burning Bright and Burning Out Fast

Likening himself to Robin Hood, Black Sam Bellamy’s pirate career was brief, lasting little more than a year. Despite its brevity, Black Sam’s career was one of the most prolific and spectacular years in the history of piracy, during which he captured over 50 ships, quite a few of them bearing rich cargoes. Collectively, those prizes made him the richest pirate in recorded history.

In contrast to other pirates who became notorious for their gratuitous cruelty, Black Sam stood out for his shows of mercy. It earned him another nickname: the “Prince of Pirates”. He met his end off Cape Cod, where the Whydah Gally was driven ashore and wrecked by a nor’easter on April 26th, 1717. The ship sank quickly, drowning Black Sam and all but two of her 145 man crew.

The Real Pirates of the Caribbean
Blackbeard. Wikimedia

9. History’s Most Famous Pirate Was Nowhere Near to Being Its Most Successful

Blackbeard, real name Edward Teach (circa 1680 – 1718), is probably the most famous pirate of all time. His actual career accomplishments as a pirate, however, were few, far in between, and relatively miniscule.

Blackbeard started his career as a privateer. He became an out and out pirate in 1716, when he joined the crew of Benjamin Hornigold, who mentored him and taught him the ropes of piracy. Blackbeard soon became first mate and second in command, and was entrusted with his own sloop to operate in conjunction with Hornigold’s main ship.

The Real Pirates of the Caribbean
Blackbeard. ThoughtCo

8. Appearances Make the Man

Blackbeard’s fame and notoriety are due in large part to his looks. His appearance was notable and terrifying, with his most defining feature being the thick and long black beard from which he derived his nickname. He was in the habit of tying it in braids, each decorated with ribbons.

Blackbeard further enhanced his ferocious image by slinging six pistols across his chest, thrusting a variety of knives and daggers in his belt and, wielding a wicked looking cutlass. To top it off, he attached slow burning matches to his beard, which sputtered and emitted thick smoke, and made him appear even more demonic. It was a psychologically effective display: many ships surrendered at first sight of the ferocious, crazy looking, bearded, and smoke spewing pirate.

The Real Pirates of the Caribbean
Blackbeard’s final battle, by Jean Leon Gerome Ferris. Neatorama

7. Queen Anne’s Revenge

Hornigold retired from piracy in 1717, but Blackbeard continued independently on his own. Soon thereafter, he seized a French ship, remodeled and equipped it with 40 cannons, renamed her Queen Anne’s Revenge, and made her his flagship. He then formed a pirate alliance, and used it to commit his most notorious act: a successful blockade of Charleston, South Carolina, holding the city hostage until he was paid a ransom.

Blackbeard accepted a royal pardon in 1718, but soon reneged and returned to piracy. So Virginia’s governor ordered an expedition to hunt him down. Led by Royal Navy Lieutenant Robert Maynard, the expedition tracked Blackbeard, and found him on November 22nd, 1718, anchored at Oracoke Island, off North Carolina. Blackbeard was outnumbered, as most of his men were ashore at the time, but he refused to surrender. He put up a fierce fight before he finally went down on the deck of his ship, after taking five bullets and over twenty sword cuts.

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Benjamin Hornigold. Golden Age of Piracy

6. The Pirate Who Ended His Days as a Pirate Hunter

Early in his seafaring career, Benjamin Hornigold (1680 – 1719) was a privateer during the War of the Spanish Succession, licensed with Letters of Marque to legally prey upon French ships. After the war, he switched from privateering to outright piracy. His first recorded act of piracy dates to 1713, when he used sailing canoes and a small sloop to capture and loot merchant ships around the Bahamas.

Eventually, Hornigold became one of the Caribbean’s most notorious pirates, before accepting a royal pardon in 1718. He then turned against his former friends and colleagues, and became a successful pirate hunter.

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Benjamin Hornigold’s ship, the Ranger. Pintrest

5. Commanding the Caribbean’s Most Powerful Pirate Ship

In 1717, Benjamin Hornigold was riding high, commanding the Carribbean’s most powerful ship, a 30 gun sloop named the Ranger. It allowed him to prey on shipping with impunity. His first mate was Blackbeard, and his protégées and acquaintances included other future notorious pirates such as Black Sam Bellamy and Stede Bonnet.

Hornigold operated mainly around the Bahamas, and his base of operations was Nassau, a notorious pirates’ nest. Hornigold and a bitter rival, Henry Jennings, transformed Nassau into a de facto Pirates’ Republic, governed by its own code of conduct and regulations. The depredations and havoc issuing from there finally forced the British authorities to send a governor, with a Royal Navy squadron, to restore order in the Bahamas and end the scourge of piracy.

The Real Pirates of the Caribbean
Benjamin Hornigold. Art Station

4. Accepting the King’s Pardon

The Bahamas’ new governor arrived in 1718, with a royal pardon for all who turned themselves in and refrained from further acts of piracy. Hornigold accepted, and the governor commissioned him to hunt down those who had not accepted the royal pardon. He turned upon his former friends and colleagues, and fell upon them with a will.

Hornigold turned out to be an even better pirate hunter than he had been a pirate. By December of 1718, he had captured ten recalcitrant pirate captains who had failed to accept the pardon, of whom nine were executed. His actions effectively brought the Pirates’ Republic in Nassau to an end, and reestablished law and order in the Bahamas. In late 1719, Hornigold was sailing about, hunting more pirates, when he drowned after his ship was caught in a storm and wrecked on an uncharted reef.

The Real Pirates of the Caribbean
Stede Bonnet. Missed in History

3. The Sad Sack Pirate

Stede Bonnet (circa 1680 – 1718), nicknamed “The Gentleman Pirate” because he had been a wealthy plantation owner in Barbados and an army major, made a terrible career choice in turning to piracy. He became famous not because of his success as a pirate, but because of the remarkable incompetence, he displayed after taking up a career he probably should have left to roughnecks better suited to its travails and vicissitudes.

Born into a wealthy family of landed gentry, Bonnet led a peaceful life for years with his wife in a profitable Barbadian sugar plantation. Then out of the blue in 1717, in some type of mid life crisis, he decided to escape marital difficulties and boredom at home by purchasing a ship, naming it the Revenge and outfitting it with cannons. Hiring a crew of 70 sailors, he then sailed off into the deep blue to become a pirate.

The Real Pirates of the Caribbean
Stede Bonnet’s flag. Amazon

2. Getting Rolled by Blackbeard

As might be expected from a rich dilettante who took to piracy on a whim, Stede Bonnet was not a very good pirate. He soon revealed himself an incompetent sailor and worse leader, who managed to seize only a few small and trifling prizes off the coasts of the Carolinas and Virginia. It was only because he paid his crew regular and generous wages – the only pirate captain to do so – that the men refrained from deposing Bonnet and electing another captain in his stead.

He came across Blackbeard in Florida, who befriended Bonnet and persuaded him to give up command of the Revenge because of his utter incompetence at piracy. Bonnet transferred to Blackbeard’s Queen Anne’s Revenge, where he remained as either a guest or de facto prisoner – sources differ. His own ship, Revenge, was taken over by one of Blackbeard’s lieutenants, whom the crew accepted as their new captain.

The Real Pirates of the Caribbean
The ending of Stede’s Bonnet’s piratical career and life. Way of the Pirates

1. Ending His Career at the End of a Rope

Not long after falling in with Blackbeard, Stede Bonnet accepted a royal pardon and a royal commission to go privateering against Spanish shipping. However, he decided to return to piracy in July of 1718. Hapless as ever, he thought that adopting the alias “Captain Thomas” and changing the name of his ship to Royal James would suffice to mask his identity. It did not.

A few weeks later, a British naval expedition came across Bonnet at anchor in the Cape Fear River estuary, and after a fight, captured him and his crew. Bonnet managed to escape, but was recaptured after a few weeks on the lam, and taken to Charleston. There, he was tried and convicted on two counts of piracy, sentenced to death by hanging, and executed on December 10th, 1718.


Where Did We Find This Stuff? Some Sources and Further Reading

James Grant Wilson, John Fiske – Appleton’s Cyclopedia of American Biography

Botting, Douglas – The Pirates (1978)

Cordingly, David – Under the Black Flag: The Romance and Reality of Life Among the Pirates (1996)

Eskify – 10 Greatest French Pirates From History

History Hit – Black Bart, the Most Successful Pirate of Them All

Johnson, Captain Charles – A General History of the Robberies and Murders of the Most Notorious Pirates (1724)

Kelsey, Harry – Sir Francis Drake, the Queen’s Pirate (1998)

Lane, Kris E. – Pillaging the Empire: Piracy in the Americas, 1500-1750 (1998)

Pirate Encyclopedia – Michel de Grammont

Pirates and Privateers – The History of Maritime Piracy: Flail of the Spaniards

Republic of Pirates – Stede Bonnet Biography

Smithsonian Magazine, July 31st, 2007 – The Gentleman Pirate

South Carolina Encyclopedia – Bonnet, Stede

Way of the Pirates – Bartholomew Roberts

Way of the Pirates – Benjamin Hornigold

Wikipedia – Calico Jack

Wikipedia – Daniel Montbars

Wikipedia – Henry Every

Woodard, Collin – The Republic of Pirates (2007)