12 of History’s Most Notorious Pirates Will Make You Want to Stay off the Seven Seas

12 of History’s Most Notorious Pirates Will Make You Want to Stay off the Seven Seas

Khalid Elhassan - November 11, 2017

Piracy – the act of violent robbery by seaborne attackers against ships or coastal areas in order to seize valuables – has been around for millennia, with the earliest documented instances in the historical record dating back to the 14th century, BC, when Mediterranean and Aegean civilizations barely survived a massive onslaught from seaborne raiders known as the Sea Peoples.

The predatorily opportunistic practice endured and flared up across the centuries, plaguing the Romans in the 1st century BC before it was suppressed by Pompey the Great, afflicting Europe and the Mediterranean with the rise of the Vikings in the Middle Ages, Ottoman corsairs during the Renaissance, massive pirate fleets that preyed upon Chinese shipping at whenever central authority weakened, and into the 21st century, where it recently flared up in the Indian Ocean with the proliferation of Somali pirates, and across the shipping lanes of the East Indies.

One of the most dramatic and fascinating periods of widespread piracy was that from the 16th to the 19th century, which includes the so-called “Golden Age of Piracy” from the 1650s to the 1730s, that saw the rise – and often grisly fall – of some of history’s best-known pirates, such as the dreaded Blackbeard, Captain Kidd, or Henry Morgan, whose colorful careers gave rise to an enduring genre of pirate fiction and movies. Following are twelve of history’s most notorious pirates from that period, spanning the Elizabethan Age to the 19th century.

12 of History’s Most Notorious Pirates Will Make You Want to Stay off the Seven Seas
Francis Drake. Biography

Sir Francis Drake

The most celebrated and renowned seaman of the Elizabethan Era, Sir Francis Drake (circa 1540 – 1596) was an English privateer and admiral who led an adventurous seafaring career during which he became the period’s greatest pirate, preying upon Spanish shipping and coastal settlements, became the second man to circumnavigate the globe after Magellan’s expedition, during which endeavor he combined exploration with opportunistic plunder, and played a leading role in defeating the Spanish Armada in 1588.

Drake went to sea at an early age, and in his teens was enlisted by his relatives, the Hawkinses, a clan of privateers who preyed upon French coastal shipping. By the 1560s, he 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 a heavy loss of life among his crew – an experience which left him with a lifelong hatred of Spain.

In 1572, he received a letter of marque from Queen Elizabeth, authorizing him to plunder any property of the Spanish crown, and armed with that authorization, he 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.

In 1577, he 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 lbs of gold, 13 chests of coins, and 26 tons of silver. His holds full of loot, he then crossed the Pacific, Indian Ocean, rounded the tip of Africa, and returned to England on September 26th, 1580, having circumnavigated the globe.

In 1585, 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, he led daring preemptive raids against Spanish fleets assembling in Cadiz and Coruna for an invasion of England and inflicted significant damage which prevented their sailing that year. The following year, the combined Spanish fleet, the famous Armada, set sail, only for Drake to play 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.

Drake’s eventful life finally came to an end in 1596, when he succumbed to a fever during an expedition against Spanish possessions in the West Indies. His career, with its turns from soldier and sailor to outright pirate, illustrates the era’s murky lines between legalized piracy, also known as privateering, whereby governments of the day issued their seafaring subjects letters of marque during times of war, authorizing them to prey upon enemy shipping, and outright piracy when those same seafarers preyed upon shipping without such a fig leaf of legality.

12 of History’s Most Notorious Pirates Will Make You Want to Stay off the Seven Seas
Francois L’Olonnais. Wikimedia

Francois L’Olonnais

Jean-David Nau, better known as Francois L’Olonnais (1630 – 1669), was one of history’s most ruthless and feared pirates, whose reputation for brutality stood out even 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”.

Born in dire poverty in France, L’Olonnais’ family sold him into indentured servitude as a child, and as such he arrived in the Caribbean at age 15, to spend the next ten years of his life toiling on Spanish plantations. He performed back-breaking menial work in harsh conditions and endured such mistreatment and sundry humiliations that, by the end of his term of indentured servitude in 1660, he had a developed a burning hatred of Spain and all things Spanish.

Changing his name to Francois L’Olonnais, he moved to Tortuga, a French island north of modern Haiti that was a nest of piracy and lawlessness at the time. There, he joined its buccaneers and showed such zeal that within a short time Tortuga’s French governor gave L’Olonnais his own ship, a letter of marque authorizing him to prey on Spanish shipping as a privateer, and turned him loose. He set himself apart with a reputation for viciousness and ferocious cruelty in the treatment of prisoners, particularly Spanish ones – an expert torturer, he 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.

Early in his career, he was shipwrecked off Yucatan, and while most of the crew survived to reach the shore, most were 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. Arriving at Maracaibo, he discovered that the citizens had fled, so he tracked them down into the surrounding jungles, and tortured them into revealing where they had hidden their valuables. He and his men then spent two months engaged in widespread rape, pillage, and murder, and 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.

12 of History’s Most Notorious Pirates Will Make You Want to Stay off the Seven Seas
Henry Morgan. Biography

Henry Morgan

One of history’s most successful pirates and namesake of a popular brand of rum, Sir Henry Morgan (1635 – 1688) was a Welsh privateer who, operating out of Port Royal, Jamaica, plundered and terrorized the Spanish Main and Spain’s Caribbean colonies in the 17th century. He grew rich off the plunder and loot, went on to become Lieutenant Governor of Jamaica, and retired to the life of a wealthy plantation owner.

He probably first arrived in the Caribbean as a member of the British expedition that seized Jamaica in 1655, and by 1666, he was second in command of a fleet of buccaneers operating against Dutch colonies during the Second Anglo-Dutch War. The following year, he rose to top command of the buccaneers and led them in the capture of Puerto Principe in Cuba, and in storming and sacking the wealthy and well-fortified city of Portobello in Panama.

In 1669, he pillaged the wealthy Spanish settlements around Lake Maracaibo in Venezuela, and in 1671, 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.

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 there 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 he remained, a wealthy plantation owner and powerful political figure, subbing as governor on occasion during that officeholder’s absence, until his death in 1688.

12 of History’s Most Notorious Pirates Will Make You Want to Stay off the Seven Seas
Henry Every. ThoughtCo

Henry Every

In addition to successfully pulling off one of the most lucrative heists in the history of piracy, Henry “Long Ben” Every (circa 1655 – disappeared 1699) was one of the few major pirates who reportedly lived to retire with his loot, without being killed in battle or arrested and executed. 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.

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

Arriving in Madagascar in 1695, Every 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 its annual pilgrimage to Mecca. In cooperation with 5 other pirate ships, Every intercepted the Mughal fleet and captured a ship whose holds yielded about £60,000 pounds – a sizeable haul in those days.

Every and his crew wanted more, however. Not long after, they caught up with the Mughal fleet’s flagship, the Ganj-i-Sawai, with 62 guns and 500 musket men, and seized it after an hours-long ferocious fight, during which the Mughal captain panicked and fled to hide below decks among concubines. After securing the vessel, Every and his crew then 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, which was the largest single haul ever scored by a pirate. Not wanting to share with the other pirate ships, Every and his men tricked them, loading their holds with the loot and arranging to meet and divide the bounty, but took off instead. The Fancy, recently modified for speed, soon out-sailed the other pirate ships, whom 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 Every disappeared from history. It was commonly assumed that he established a new identity somewhere and lived his remaining days in great wealth, but some sources claim that he returned to England, only to be swindled out of his riches, and ended his days an impoverished pauper.

12 of History’s Most Notorious Pirates Will Make You Want to Stay off the Seven Seas
Captain Kidd in New York Harbor, by Jean Leone Gerome Ferris. Wikimedia

Captain Kidd

There was little in the background or life of the Scotsman William Kidd, better known to history as Captain Kidd (circa 1645 – 1701), to indicate that he would end up swinging from the gallows, executed as one of the era’s most notorious pirates. He had been one of New York City’s leading citizens, a friend of at least three of the colony’s governors, and among other civic activities, he had played a prominent role in building the city’s now historic Trinity Church.

Kidd’s first seafaring command was as a privateer, commissioned in 1689 by the governor of Nevis to fight off French ships, and granted letters of marque authorizing him to prey on French vessels for the duration of hostilities between Britain and France. Later, he was issued additional letters of marque by the governors of New York and the Massachusetts Bay Colony.

In 1695, Kidd’s mission was expanded and presented with a letter of marque signed by King William III, he was given a roving commission to attack pirates in the Indian Ocean. The voyage started inauspiciously: sailing out of London in a newly equipped ship, the 34 gun and 150 man crew Adventure Galley, Kidd offended a Royal Navy captain by failing to salute his warship in the Thames, so he retaliated by stopping the Adventure Galley and seizing half of its crew to press them into the Royal Navy.

Crossing the Atlantic short-handed, Kidd made it to New York, where he replenished his crew with what out-of-work seafarers he could find. Most them turned out to be hardened criminals and former pirates. Sailing into the Indian Ocean, a third of Kidd’s crew died of cholera by the time they reached the Comoros islands, and he was unable to find the pirates he had been sent to hunt down.

The enterprise seemed a failure, and the crew, getting antsy, urged him to attack some passing vessels in order to make the voyage worth their time. When Kidd declined, his men threatened mutiny. Under pressure – and also to recoup his investment – he gave in and reluctantly started attacking ships not covered by his privateering letters. By 1698, he had abandoned reluctance and any pretense of privateering and turned full pirate. That year, he sealed his fate when he attacked a British East India Company ship. The powerful company exerted its influence in London, and Kidd was declared a pirate.

Unbenknownst to him, by the time he returned to the American Colonies, Kidd’s public image had been transformed into that of an infamous pirate, and attitudes towards piracy had changed from the wink, wink, nudge, nudge, which prevailed when he began his voyage. Now, crackdown was in the air, and the authorities were eager to make an example of somebody.

Kidd was arrested soon as he arrived in Boston, and sent in chains across the Atlantic for prosecution in London. There, word of his previous connections with government elites caused a scandal, and the powerful supporters whom he had expected to defend him abandoned him in droves. He was swiftly tried and convicted, and on May 23, 1701, was hanged, after which his body was left to rot in a cage on the Thames for all to see.

12 of History’s Most Notorious Pirates Will Make You Want to Stay off the Seven Seas
Benjamin Hornigold. Golden Age of Piracy

Benjamin Hornigold

Benjamin Hornigold (1680 – 1719) started off as a privateer during the War of the Spanish Succession, licensed with letters of marque to legally prey upon French merchant shipping, and after the war, turned from privateering to outright piracy. Eventually, he became one of the Caribbean’s most notorious pirates, before accepting a royal pardon in 1718, after which he turned against his former friends and colleagues and became a successful pirate hunter.

Hornigold’s 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. By 1717, he commanded the most powerful ship in the region, a 30 gun sloop, the Ranger, which allowed him to prey on shipping with impunity. His first mate was Edward Teach, later known as Blackbeard, and his proteges and acquaintances included other future notorious pirates such as Black Sam Bellamy and Stede Bonnet.

Hornigold’s operated in the main around the Bahamas, and his base of operations was Nassau, which had become 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 piratical depredations and havoc issuing from there finally forced the British authorities in London to send a governor, with a Royal Navy squadron, to restore order in the Bahamas and end the scourge of piracy.

Arriving in 1718, the new governor brought a royal pardon for all who turned themselves in and refrained from further acts of piracy, and Hornigold was one of those who accepted. The new governor commissioned him to hunt down those who had failed to turn themselves in and accept the royal pardon, and accepting the commission, Hornigold turned upon his former friends and colleagues and fell upon them with a will.

He turned out to be an even better pirate hunter than he had been a pirate, and by December of 1718, Hornigold had captured 10 recalcitrant pirate captains who had failed to accept the pardon, of whom 9 were executed. His actions effectively brought the Pirates’ Republic in Nassau to an end and re-established British control, and law and order, in the Bahamas. He was sailing about, hunting more pirates when he drowned after his ship was caught in a storm and wrecked on an uncharted reef in late 1719.

12 of History’s Most Notorious Pirates Will Make You Want to Stay off the Seven Seas
Stede Bonnet. Missed in History

Stede Bonnet

Nicknamed “The Gentleman Pirate” because he had been a wealthy plantation owner in Barbados and an army major before turning to piracy, Stede Bonnet (circa 1680 – 1718) earned his fame or infamy not because of his success as a pirate, but because of the remarkable incompetence, he displayed after taking up a career in piracy that he had no business pursuing, and probably should have left to roughnecks better suited to its travails and vicissitudes.

Born into a wealthy family of landed gentry, Bonnet had led a peaceful life for years, living 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.

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

He came across Blackbeard in Florida, who befriended Bonnet and persuaded him into giving 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 a guest. His own ship, Revenge, was taken over by one of Blackbeard’s lieutenants, whom the crew accepted as their new captain.

Soon thereafter, Bonnet accepted a royal pardon and a royal commission to go privateering against Spanish shipping. However, he decided to return to piracy in July 1718, and, hapless as ever, 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.

12 of History’s Most Notorious Pirates Will Make You Want to Stay off the Seven Seas
Stede Bonnet Hanging. Way of the Pirates

The following month, 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.

12 of History’s Most Notorious Pirates Will Make You Want to Stay off the Seven Seas
Samuel Bellamy. Crime Museum

Black Sam Bellamy

Samuel Bellamy, better known as Captain Black Sam Bellamy (1689 – 1717), earned the nickname “Black Sam” not because of any fell acts or dark deeds of piracy, but 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 was a combat veteran who’d already taken part in a number of sea battles with the Royal Navy by the time he reached manhood.

In 1715, he 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, they turned to piracy to recoup their investment. 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 pirate 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. His biggest haul was the Whydah Gally, which Bellamy overtook on its maiden voyage after a 3-day chase, and captured it with a rich haul of gold, ivory, indigo, and other high-value goods. Upgrading it with extra cannon and turning it into his flagship, Bellamy then fell upon the shipping lanes to the Carolinas and New England and feasted.

Likening himself to Robin Hood, Bellamy’s pirate career was brief, lasting little more than a year, but it was one of the most prolific and spectacular years in the history of piracy, during which he captured over 50 ships – which made him the richest pirate in recorded history. He stood out for his shows of mercy, which 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, quickly sinking and drowning Bellamy and all but two of her 145-man crew.

12 of History’s Most Notorious Pirates Will Make You Want to Stay off the Seven Seas
Blackbeard. Florida Memory


Edward Teach, better known as Blackbeard (circa 1680 – 1718), is probably the most famous pirate of all time. He started his career as a privateer, and in 1716 joined the crew of Benjamin Hornigold, who mentored Blackbeard and taught him the ropes of piracy, and soon made him his first mate and second in commanded, entrusted with his own sloop to operate in conjunction with Hornigold’s main ship.

His appearance was notable and terrifying, with his most defining feature 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. He 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, and many ships surrendered at first sight of the ferocious and crazy-looking bearded and smoke-spewing pirate.

After Hornigold retired from piracy in 1717, Blackbeard continued independently on his own. Soon thereafter, he seized a French ship which he remodeled and equipped with 40 cannons, and renaming her the Queen Anne’s Revenge, 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.

In 1718, he accepted a royal pardon, but soon reneged and returned to piracy. Virginia’s governor then ordered an expedition to hunt him down, led by Lieutenant Robert Maynard of the Royal Navy. Maynard tracked Blackbeard with two sloops, and found him on November 22nd, 1718, at anchor on the inner side of Ocracoke Island, off North Carolina. Blackbeard was outnumbered, as most of his men were ashore at the time, but he refused to surrender and 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.

12 of History’s Most Notorious Pirates Will Make You Want to Stay off the Seven Seas
Calico Jack Rackham. Wikimedia

Calico Jack

John Rackham, better known as Calico Jack (1682 – 1720), is one of the best-known pirates of the Golden Age of Piracy, not because he was particularly successful or much good at being a pirate – compared to other famous pirates, his career was middling and his accomplishments mediocre – but because of his associations with other, more successful pirates, his venality and backstabbing which stood out even in a profession built on venality and backstabbing, because his first mate designed the Jolly Roger flag, and because his crew included two famous female pirates, Anne Bonney and Mary Read.

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

As captain, Rackham 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 Bonney, the future pirate, grew complicated and ended with the Rackham and Bonney stealing a sloop to slip out of the Bahamas, thus voiding Rackham’s recent pardon.

In October of 1720, a pirate hunter chanced upon Rackham’s ship at anchor, while Calico Jack and most of his men were too drunk to offer effective resistance. The only fight was made by the women, Anne Bonney 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 – had little sympathy for him, and when he grew maudlin while bidding her goodbye before his execution, she reportedly sneered: “if you had fought like a man, you would not hang now like a dog!” He 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.

12 of History’s Most Notorious Pirates Will Make You Want to Stay off the Seven Seas
Black Bart. Owlcation

Bartholomew “Black Bart” Roberts

Considered the most successful pirate of the Caribbean, Bartholomew “Black Bart” Roberts (1682 – 1722) 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, Roberts had been an officer aboard a slaver that was captured by pirates, who forced him to join them. Within 6 weeks, he had impressed his new crewmates so much that when their captain was killed, the pirates elected Roberts their new captain. His career as a pirate captain got off to a spectacular start when, sailing to South America, Roberts came upon a Portuguese treasure fleet assembling in a bay in northern Brazil. Pretending to be one of the convoys, Roberts slipped into the fleet, a wolf in sheep’s clothing. That night, he quietly seized one ship and forced its captain to point out the fleet’s richest vessel, then captured it and fled before the Portuguese escort warships caught on to 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 pirate career struck a chord and made Roberts. Sailing north into the Caribbean, pirates flocked to his side, and he put them to good use. At the height of his career, he commanded a fleet of four pirate ships and over 500 pirates, and 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, Black Bart captured and looted over 470 ships.

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, he 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.

12 of History’s Most Notorious Pirates Will Make You Want to Stay off the Seven Seas
Cheung Po Tsai. History of Piracy

Cheung Po Tsai

Cheung Po Tsai (1783 – 1822), whose name translates as “Cheung Po, the Kid”, was a poor fisherman’s son who went on to become a notorious Chinese pirate operating in the vicinity of modern Hong Kong. He became legendary because of a treasure he supposedly buried in a cave that bears his name on Cheung Chau island southwest of Hong Kong.

Cheung was kidnapped at age 15 by a pirate who pressed him into his crew. The teenager quickly took to piracy, exhibited a precocious talent for the new career suddenly thrust upon him, and rose swiftly through the ranks. Before long, Cheung had become his kidnapper’s favorite protege and subordinate and ended up getting adopted by him and his wife. After his adoptive father’s untimely death by drowning, his widow and Cheung’s adoptive mother took over his pirate fleet, and Cheung became her right-hand man. The pair soon developed an incestuous affair and married, after which Cheung took charge of the piracy business from his wife/ adoptive mother.

Cheung’s scale of piratical operations far exceeded anything seen in the Caribbean during the Golden Age of Piracy, and at the height of his career, he commanded more than 600 ships and over 50,000 men. With that massive armada, Cheung and his pirates effectively controlled and held for ransom the shipping lanes around southern China.

His massive depredations and the resultant outcry finally compelled the Chinese authorities to launch a commensurately massive campaign to eradicate piracy and restore order. In 1810, seeing the writing on the wall and deciding that discretion was the better part of valor, Cheung accepted a pardon, joined the Chinese navy, and spent the rest of his life as a pirate hunter.