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

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

Khalid Elhassan - November 11, 2017

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.