Although pirates have a long history dating back to antiquity, they continue to fascinate many of us. The golden age of piracy took place between the 17th and 18th centuries, yet these buccaneers of the seas are not forgotten! ☠️
From legends to real-life characters ruthlessly plundering ships the world over, we’ve taken a closer look at the most emblematic figures of this very special world. Some of them are true heroes in our eyes. It’s time for you to find your own, if you haven’t already, and become a true modern-day pirate. Let’s board!
15) The Barbarossa Brothers
Hailing from the Barbary Coast of North Africa, brothers Aruj and Hizir Barbarossa (which means “red beard” in Italian) amassed wealth by capturing European ships in the Mediterranean. They began targeting the Spanish when Aruj lost an arm in battle. In 1516, the Ottoman sultan gave Aruj responsibility for the entire Barbary coast, a position Hizir took over two years later after his brother’s death. 💀
Hizir, known as Khair-ed-Din, spent the rest of his life fighting various Christian enemies, including a “Holy League” fleet specially formed by the Pope to destroy him. The mere mention of their names immediately conjures up images of fierce sailors wielding swords in the Mediterranean. In the 16th century, the brothers attacked numerous coastal towns with their band of pirates and became among the most influential men in the region.
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14) Francis Drake
Francis Drake, nicknamed “my pirate” by Queen Elizabeth I, was one of the privateers known as the “Sea Dog” authorized by the English government to attack Spanish shipping. Drake made his most famous voyage from 1577 to 1580, becoming the first English captain to circumnavigate the globe. On this voyage, he lost four of his five ships, executed a crew member, raided various Spanish ports and captured a Spanish ship laden with treasure. Queen Elizabeth, delighted, immediately knighted him on his return. Eight years later, Drake helped defeat the Spanish Armada. 🇪🇸
Noble to some, outlaw to others, Drake devoted his time to piracy and the slave trade in the Caribbean. The raids he led, particularly on the Spanish colonies in Central America, yielded some of the biggest catches in the history of piracy.
13) L’Olonnais
L’Olonnais was one of the many buccaneers – a combination of state privateers and outlaws – who roamed the Caribbean in the mid-to-late 17th century. Also known as Jean-David Nau, “L’Olonnais” is said to have begun attacking Spanish ships and coastal settlements. From the moment he arrived as an indentured servant, he earned a reputation for great cruelty. 😵
Seventeenth-century pirate historian Alexander Exquemelin wrote that L’Olonnais cut his victims into pieces or tightened a rope around their necks until their eyes popped out. Suspecting betrayal, he even cut out a man’s heart and ate a piece. But karma caught up with him in 1668, when, according to Exquemelin, he was captured and eaten by cannibals…
Despite all the atrocities he may have committed, he also scored many successes, capturing many ships and pillaging many towns. This pirate was probably one of the most effective captains for land attacks. He attacked the cities of Maracaibo and Gibraltar in the Gulf of Venezuela, and later, with his powerful fleet and over 700 buccaneers, quickly captured the port of Puerto Cabello.
12) Henry Morgan
Perhaps the most famous pirate of the buccaneering era, Henry Morgan is said to have once ordered his men to lock the inhabitants of Puerto Príncipe, Cuba, in a church in order to plunder the town with impunity. He then seized Porto Bello, Panama, partly using a human shield of priests, women and the mayor. Over the next few years, he carried out further brutal raids against two towns in Venezuela and Panama City.
Although he was briefly arrested in 1672, Morgan eventually became governor of Jamaica in 1678 and again from 1680 to 1682. Ironically, during his administration, the Jamaican Parliament passed an anti-piracy law and Morgan even participated in the prosecution of pirates. 🗺
Despite being one of the most famous pirates in history, Captain Morgan’s status as a pirate is still uncertain. Different accounts refer to him as a pirate, privateer or buccaneer in different places. He is best known for his attacks on Spanish ships and for pillaging towns such as Puerto Principe, which had to be completely rebuilt after Morgan and his men had passed through.
11) Captain Kidd
Once a respected privateer, Captain William Kidd set sail in 1696 on a mission to hunt down pirates in the Indian Ocean. However, he soon became a pirate himself, capturing ships such as the Quedagh Merchant and killing one of her crew with a wooden bucket. After a major defeat, he found himself with a skeleton crew for the return voyage, which included a stop on New York’s Gardiners Island to bury treasure. 🧱
After clashing with the powerful British East India Company, Kidd was arrested before he could return to England. He was then tried, sentenced to death and executed. His decomposing body was displayed on the banks of the Thames, serving as a warning to other pirates.
He is known as a ruthless pirate and was captain of one of the most famous pirate ships ever built. His most daring act was the plundering of a treasure ship, almost twice the size of his own ship, along the Indian Malabar coast.
10) Calico Jack
John Rackham, better known as Calico Jack, was pardoned for his piratical misdeeds in 1719. However, the following year, he set sail again after seizing a 12-gun ship in the Bahamian port of Nassau. Among his dozen followers were two of the only female pirates ever to sail Caribbean waters. One of them, Anne Bonny, had left her husband to join Rackham, while the other, Mary Read, posed as a man. 🧑✈️
Pioneer of the Jolly Roger flag, Calico Jack Rackham was a Caribbean buccaneer who didn’t rack up many epic plunders, but he is known for his relationship with Anne Bonny. Captured in Jamaica in 1720, Rackham was hanged, his body smeared with tar and displayed as a warning to other pirates, in a place now known as Rackham’s Cay.
9) Madame Cheng
In 1805, Madame Cheng’s husband, Cheng Yih, formed what quickly became the largest pirate confederation in history. Upon her husband’s death two years later, Madame Cheng took the reins and expanded the enterprise even further, commanding some 1,800 ships and 70,000 men at its peak. 💪
With the help of Cheung Po Tsai, her husband’s adopted son and also her lover, she demanded money in exchange for protecting coastal communities, attacked ships in the South China Sea and even kidnapped seven British sailors. Madame Cheng was pardoned in 1810 when the Chinese authorities began to crack down on piracy. A former prostitute, she rose to prominence running a vast opium trafficking operation.
8) Anne Bonny
The most famous female pirate in history was as formidable as her male counterparts, as well as being beautiful and intelligent. The daughter of plantation owners, Anne left her settled life in the early 1700s to take to the sea. She joined Calico Jack Rackham’s ship disguised as a man, but was spared the death penalty when the crew was captured, as she was pregnant with Rackham’s child, according to legend. ✍️
When Anne Bonny moved from Ireland to Nassau, she thought it would offer her a wonderful opportunity for a new life. However, she soon found herself in an unsatisfactory marriage that left her disappointed. To protect herself, she had to constantly disguise herself as a man and adopt masculine behavior, including heavy drinking and fighting…
If you’re interested in the legend of Anne Bonny, why not learn how to draw a pirate flag with us!
7) Captain Samuel Bellamy
Although he died at the age of 28, “Black Sam” Bellamy left his mark on the world of New World piracy with his daring captures of ships, including the famous Whydah Gally, a slave ship filled with a fortune in gold, silver and other goods. In 1717, Bellamy made her his flagship, but the ship sank in a storm that same year.
He is remembered for his exceptional courage. According to the testimonies of his men, he was more mad than brave. He never hesitated to attack ships much larger and better equipped than his own, often taking his rivals by surprise. Legend has it that his daring was often rewarded!
6) Bartholomew Roberts
The “Black” Bart Roberts was one of the most famous pirates of the golden age of piracy. He plied the waters off Africa and the Caribbean islands, capturing over 400 ships in just four years. This remarkably cold-blooded sailor left few survivors on board, which earned him intense tracking by the British government and ultimately led to his death at sea.
A notorious but equally intelligent pirate, he stumbled into piracy almost by accident. When his partner, Howell Davis, died, Roberts found himself young and in charge of a pirate ship. He was brave and daring. Legend has it that he pillaged several ships before setting them on fire with slaves still aboard…
5) Henry Every
This whimsical pirate, captain of a ship called “Fancy”, is famous for making the most of his pirate career in a short space of time. He is known for plundering two large ships one after the other, amassing a huge treasure. This testifies to his excellent strategic skills. But he’s most famous for never having been captured. After his enormous plundering, he withdrew and disappeared, reappearing only in stories and legends.
With his fleet of five ships and a crew of highly experienced pirates, he captured many ships, including the Great Mughal’s famous “Gang-i-Sawai”. His fame as a pirate captain and his ability to stay alive and retire peacefully make him an exceptional figure among pirates.
Henry Every’s story: He began his career as a sailor in the British Royal Navy, but became a pirate following a mutiny. He sailed the Indian Ocean and the Red Sea, earning a reputation as an efficient and formidable pirate. Although he only attacked a few ships, they contained some of the most impressive treasures, such as gold and jewels, making him the richest pirate of his time. Since he was so sought-after, he wisely retired and disappeared into obscurity with his riches.
4) Anne Bonny and Mary Read
Presenting an extraordinary story of female strength in a man’s world, these two female pirates were exceptional figures in the world of piracy. They were stubborn, rational and clearly knew what they didn’t want in life.
Fate led them to piracy, but it was their skill as efficient navigators that earned them their place in the history books of the world’s famous pirates. Both joined the pirate crew of Calico Jack, but left when the ship and its captain were finally captured. Legend has it that Anne and Captain Jack even had a romantic relationship. It is also said that the friendship between Anne and Mary turned into a love affair between the two women.
3) Peter Easton
Interestingly, Peter Easton isn’t as well known as the other pirates on this list, despite all his successes. Captain Easton was formerly a servant of the English Crown, but turned to piracy. He is best known for never being defeated by those charged with hunting him down.
His vast and powerful fleet numbered 40 ships and over 1,500 men at its peak. His most notable victory came in 1610 in Newfoundland against Sir Richard Whitbourne’s fleet, where he triumphed over 30 ships. He also captured many imposing ships, including the famous Spanish San Sebastian.
2) Cheng I Sao
Now imagine bringing together all the pirates and ships we’ve mentioned earlier in this article to form one big team. That would be phenomenal power, wouldn’t it? Well, according to the legends surrounding Cheng I Sao, it’s easy to say that the combination of all these pirates wouldn’t be enough to rival the striking power of this woman…
At her peak, the former prostitute controlled over 1,500 ships and had a crew of 80,000 sailors, making her one of the largest naval armies in history. This female pirate captain used her huge army to plunder cities and attack ships along the coast of the South China Sea.
1) Blackbeard
Born as Edward Teach, Blackbeard intimidated his enemies by curling smoldering locks into his long braided hair and carrying multiple pistols and daggers across his chest. In November 1717, he captured a French slave ship, later renamed Queen Anne’s Revenge, and fitted it with 40 cannons. With this extra firepower, he then blockaded the port of Charleston, South Carolina, until the townspeople met his demands for a large chest of medicine.
After keeping a low profile for a few months in North Carolina, Blackbeard was killed in a battle with the British navy. Legend has it that he received 20 stab wounds and five bullet wounds before succumbing. The golden age of piracy, of which Blackbeard was a major part, lasted just a few more years. However, numerous books, plays and films, such as Treasure Island and Pirates of the Caribbean, have popularized a romanticized version of this era.
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