The Golden Age of Piracy’s Most Terrifying Pirates

18. From Privateer to Pirate

The real life inspiration behind the fictional protagonist of The Successful Pyrate was born in Plymouth, England, and went to sea at an early age. By 1694, John Aery was First Mate in the Charles II, a privateer that served the king of Spain, when he led its disgruntled crew in a mutiny that seized the ship. Avery was elected by his fellow mutineers to captain the seized the ship, which was renamed the Fancy. He then made the jump from privateer – semi-official pirates authorized by governments to prey on enemy ships – to outright pirate. He issued a proclamation to assure English vessels that they had nothing to fear from him, and that he would only attack foreign ships. The proclamation was not the worth the paper it was written on: Avery’s first act of piracy was to plunder provisions and supplies from three English merchantmen.

17. John Avery in the Indian Ocean

After his first act of piracy, Avery sailed into the Indian Ocean and arrived in Madagascar in 1695. There, he had the Fancy refitted and modified for speed. Soon thereafter he seized a French ship, and convinced 40 of its sailors to join him. Eventually, with a crew of about 150 men, he sailed north towards the Red Sea, to intercept the Indian Mughal fleet as it returned from the annual pilgrimage to Mecca. The Mughal fleet was the Indian Ocean’s greatest prize, and its capture promised to yield fabulous riches. Avery joined forces with five other pirate ships, and on September 7^th, 1695, they spotted their target, a 25-ship Mughal convoy.

16. The Capture of the Mughal Flagship

The richest prize of the Mughal convoy was the fleet’s flagship, the Ganj-i-Sawai, which carried 62 guns and 500 men armed with muskets. After an hours-long ferocious fight in which its Mughal captain panicked and fled to hide below decks among concubines, the pirates seized the Ganj-i-Sawai. After they secured the vessel, Avery and his crew went on a days-long orgy of assaults and torture. The loot from the ship came to about £600,000 in gold, silver, precious metals and goods. It was the largest single haul ever scored by pirates. There is no honesty among thieves, however, and Avery and his men did not want to divide the loot with the other pirate ships. So they resorted to trickery to cheat the others out of their share.

15. No Honor Among Thieves

Avery’s men loaded their hold with the loot and made arrangements with the other ships’ pirates to meet and divide the bounty, but took off instead. The Fancy, recently modified for speed, soon out-sailed the other pirate ships that followed in her wake in impotent rage, until she disappeared below the horizon. Avery’s ship made it to the Caribbean, and after the loot was divided, the crew split up and its captain disappeared from history. It was commonly assumed that Avery had made a clean escape, established a new identity somewhere, and spent the rest of his life in the lap of luxury. However, some sources claim that he returned to England, only to get swindled out of his riches and end his days an impoverished pauper.

14. The Terrifying Exterminator of the Spanish

French buccaneer Daniel Montbars (1645 – disappeared 1707), better known as Montbars the Exterminator, earned his nickname and then some. One of the seventeenth century’s most feared pirates, Montbars became known as the Exterminator because of the excessive glee and bloody mindedness he displayed in killing Spaniards. Born into a wealthy family, Montbars was raised and educated in France as a gentleman. In childhood, he read of the cruelties visited by the Conquistadors upon the New World natives, and came to hate Spain and all things Spanish. Montbars joined his uncle in the French Royal Navy in 1667, and accompanied him to the Caribbean. There, his anti-Spanish sentiment grew in leaps and bounds when his ship was sunk in a battle against Spaniards, during which his uncle was killed.

13. From Naval Officer to Pirate

After his uncle’s death, Montbars left the French Navy and headed to the buccaneer haven of Tortuga, an island off Haiti’s coast. Between his professional expertise as a naval officer, and his immense hatred of Spain, the buccaneers’ main foe, Montbars was welcomed with the open arms. Before long, he was captain of his own buccaneer ship. He made a name for himself in an 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“.

12. The Piratical Rampage that Terrorized the Spanish Main

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 Puerto Rico, Mexico, and Cuba. On Venezuela’s coast, he sacked and burned the towns of San Pedro, Porto Caballo, Maracaibo, and Gibraltar, among numerous other settlements and forts. His cruelties during this rampage earned Montbars the “Exterminator” nickname. He gave no quarter, and tortured captured Spaniards. 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.

11. History’s Most Famous Pirate

Blackbeard, birth name Edward Teach (circa 1680 – 1718), is probably the most famous pirate of all time. His early life is shrouded in mystery, but he started his seafaring career as a privateer – private citizens issued letters of marque by their sovereigns, authorizing them to prey on enemy ships. In 1716, he joined the crew of the pirate Benjamin Hornigold, who mentored Blackbeard and taught him piracy’s ropes. Blackbeard showed himself capable, and rose rapidly to become Hornigold’s first mate. Soon, he rose even further, and became second in command, entrusted with his own sloop to operate in conjunction with Hornigold’s main ship.

10. Blackbeard Put in a Lot of Work to Appear Terrifying

Blackbeard went to great lengths to stand out visually, and appear terrifying to his opponents. His greatest defining feature, and the source of the name by which he became famous or infamous, was a thick and long black beard. Blackbeard often plaited his beard into braids, and decorated each braid with colorful ribbons. His already ferocious appearance was further enhanced by slinging six pistols across his chest, thrusting a variety of knives and daggers into his belt and boots, and carrying a wicked looking cutlass. To top it off, he attached to his beard slow burning matches that sputtered and sent forth clouds of thick smoke, which made him appear even more demonic. It was a psychologically effective display, and many ships surrendered as soon as they caught sight of the ferocious, crazy looking, and smoke-spewing pirate.

9. Queen Anne’s Revenge

After his mentor Hornigold retired from piracy in 1717, Blackbeard continued his piratical career, now on his own hook. Soon thereafter, he seized a French ship, which he remodeled and equipped with 40 cannons, renamed it Queen Anne’s Revenge, and made her his flagship. Blackbeard then formed a pirate alliance, and used it to commit his most notorious act: a successful blockade of Charleston, South Carolina. He held the city hostage and wreaked havoc on the seaborne trade and commerce upon which its economy depended, until he was paid a ransom.

8. A Terrifying Pirate’s Dramatic End

In 1718, Blackbeard accepted a royal pardon offered to those who agreed to quit piracy. However, earning an honest living did not agree with him, so he changed his mind soon thereafter, reneged, and resumed his piratical ways. Virginia’s governor then ordered an expedition to hunt him down, led by a Lieutenant Robert Maynard of the Royal Navy. Maynard tracked Blackbeard with two sloops, and found him on November 22^nd, 1718, at anchor on the inner side of Oracoke Island, off North Carolina. Most of Blackbeard’s men were ashore, so he found himself severely outnumbered when Maynard’s expedition hove into view. Nonetheless, the notorious pirate refused to surrender and put up a ferocious fight during which he was shot five times and received more than twenty sword cuts, before he finally went down on the deck of his ship.

7. The Caribbean’s Most Successful Pirate?

Bartholomew “Black Bart” Roberts (1682 – 1722) was one of the most successful pirates of the Caribbean. He captured and looted more ships during his career than his famous contemporaries Blackbeard, Jack Rackham, Francis Sprigg, and Edward Low put together. His spectacular success 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 crewmates so much that when their captain was killed, the pirates elected Bart to replace him. He soon got over any doubts he might have had about his new career, and took to piracy with a will. As seen below, few pirates ever began their career with as big a bang as did Black Bart.

6. A Stellar Start to a Piratical Career

Black Bart kicked off his pirate captain career 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, he 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 him famous. He sailed north into the Caribbean, and other pirates flocked to his side. Black Bart put them to good use, and at the height of his career, he commanded a fleet of four pirate ships and over 500 pirates.

5. Black Bart’s Cruelty

Black Bart owed much of his success to organizational and leadership abilities, combined with charisma and daring that inspired and encouraged his men. In only four years, he captured and looted over 470 ships. He was cruel and sadistic, and relied on terror and a frightening reputation to ensure 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 shackled slaves aboard. A bloodthirsty man, Black Bart’s end was appropriately bloody: in 1722, he decided to fight it out with a Royal Navy ship, 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 they surrendered.

4. The Golden Age of Piracy’s Most Terrifying Pirate?

Few pirates were as ruthless as Jean-David Nau, better known as Francois L’Olonnais (1630 – 1669). One of history’s most scariest pirates, his reputation for brutality and macabre acts stood out even in an age and within a profession where brutality and the macabre were 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 the Spaniards”. Born in dire poverty in France, L’Olonnais was sold by his family into indentured servitude as a child. It was in that capacity that he arrived in the Caribbean as a fifteen-year-old, to toil away the next ten years of his life on Spanish plantations. The menial work he performed was back-breaking, and the conditions were atrocious.

3. A Vendetta Against Spain and the Spanish

L’Olonnais endured so much mistreatment and so many humiliations that, by the end of his term of indentured servitude, he had come to hate Spain and all things Spanish. The recently indentured Jean-David Nau changed his name to Francois L’Olonnais and moved to Tortuga, the French buccaneer haven island north of modern Haiti, where Montbars the Exterminator, above, also got his start. L’Olonnais joined the buccaneers, and showed great zeal in his new profession. That attracted the attention of the island’s French governor, who gave him a ship, a letter of marque that authorized him to prey on Spanish ships as a privateer, and turned him loose. L’Olonnais set himself apart with excessive viciousness and cruelty in the treatment – or more accurately, mistreatment – of prisoners, especially Spanish ones.

2. L’Olonnais Was Truly Terrifying

An expert torturer, Francois L’Olonnais got up to some pretty macabre stuff. Among other things, he liked to slice off strips of his victims’ flesh, burn them, or tighten ropes around their skulls until their eyeballs popped out of their sockets. Early in his career, he was shipwrecked off Yucatan. A majority of the crew survived and made it to shore, only for most of them to perish soon thereafter when Spanish soldiers found and fell upon them. To survive, L’Olonnais covered himself in blood and viscera, and hid among the corpses. Later, he snuck into a nearby town that was celebrating the deaths of the pirates, and arranged for an escape back to Tortuga. L’Olonnais resumed his depredations against Spain and the Spaniards, and in 1666 he assembled a fleet of eight ships and 440 pirates to attack Maracaibo in modern Venezuela.

1. A Terrifying Pirate’s Terrifying End

En route to Maracaibo, L’Olonnais captured a Spanish treasure ship, which yielded 260,000 Spanish dollars, plus gemstones and cocoa beans. Maracaibo’s citizens had fled by the time L’Olonnais arrived. So he tracked them down in the nearby jungles, and tortured them until they revealed where they had hidden their valuables. He and his men then indulged in a two-month-orgy of assault, pillage, and murder. They finally torched the town and tore down its fortifications before they left. A year later, 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. L’Olonnais disembarked and led his men inland in search of food, only to get captured, killed, and eaten by an indigenous tribe.

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

Appleton’s Cyclopedia of American Biography – Montbars

Baer, Joel H. – Pirates of the British Isles (2005)

Cordingly, David – Under the Black Flag: The Romance and Reality of Life Among the Pirates (1997)

Encyclopedia Britannica – John Avery

Eskify – 10 Greatest French Pirates of All Time

History Collection – These Vicious Crimes Will Make You See the Medieval Era in a New Light

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

Marley, David – Pirates of the Americas (2010)

Pendered, Norman C. – Blackbeard, the Fiercest Pirate of All (1975)

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

Queen Anne’s Revenge Project – Blackbeard: History of the Dreaded Pirate

Rogozinski, Jan – Honor Among Thieves: Captain Kidd, Henry Every, and the Pirate Democracy in the Indian Ocean (2000)

Sanders, Richard – If a Pirate I Must Be…: The True Story of “Black Bart”, King of the Caribbean Pirates (2009)