10 Of The Most Famous Pirates, Male And Female, Who Ruled The Seas!

There was a Golden Age of Piracy, and that’s not just figurative. It was literally true! Men and women made untold fortunes in gold, silver, jewels, and goods while riding the high seas and bringing their foes low… often down to the depths of Davey Jones’ locker. And many of them became famous pirates who are still well remembered today. Be they buccaneers, privateers, corsairs, freedom fighters, or just murderous thieves, one thing’s for sure – they burned brightly for a short time, and their remarkable (and sometimes savage) lives are now the stuff of legends. Here are 10 of the most famous pirates, women and men, who terrorized the seas all over the world.

Captain Morgan: Drinking In Success

Captain Morgan, a famous pirate in a category of his own. (Public domain)

Captain Morgan (Welsh, 1635-1688 AD) is now a well-known brand of rum, but the man behind the booze is perhaps the most famous pirate of the buccaneering era. Henry Morgan's early life is unknown, but most historians agree that he was born into a farming family in south Wales. Mystery also surrounds the career path which led him to become a legendary privateer, but nevertheless he ended up terrorizing Spain’s Caribbean colonies in the late 1600s AD. Henry Morgan once purportedly ordered his men to lock the villagers of Puerto Príncipe, Cuba, inside a church so they could plunder the town unhindered. His greatest achievement was capturing wealthy Panama City with 30 ships and 1200 men. Morgan subsequently earned the name El Diablo, for he set the Caribbean alight in his quest for gold, silver, and jewels. He was briefly arrested in 1672 AD, was knighted in England, and served as Governor of Jamaica, living respectfully until his death at age 53.

Sayyida al-Hurra: Bowed To No One

Sayyida al-Hurra: This famous pirate was a woman to be reckoned with. (Oxygene Tetouan / CC BY-SA 4.0)

Sayyida al-Hurra (Iberian, 1485-1561 AD) was a notorious female pirate who lived between the 15th and 16th centuries AD. Her father was a tribal chief, and her mother was a Christian who converted to Islam. As the child of a nobleman, Sayyida al-Hurra was provided with an excellent education, being tutored in such subjects as mathematics, theology, and languages. The title Sayyida al Hurra means "noble lady who is free and independent; the woman sovereign who bows to no superior authority." At some point, she became a pirate. Some have speculated that she never forgot the fall of Granada and vowed to avenge this loss, as well as to retake Andalusia from the Christians. Although she was not able to take the Spanish and Portuguese head on, she instead wreaked havoc on their sea trade via piracy. In time, she formed an alliance with the infamous pirate Oruç Reis (one of Redbeard’s brothers). Although she was hated by her European enemies, her fall from power wasn’t from outsiders but was an inside job. She was overthrown by her son-in-law and stripped of property and power.

l’Olonnais The Cruel: Flail Of The Spanish

François l'Olonnais: The famous pirate of France who was bloodthirsty and was eaten by cannibals in the end. (Public domain)

François l'Olonnais (French, c. 1630 – c. 1669 AD) is considered one of the cruelest and bloodthirsty pirates of all eras. His real name remains a mystery, but it’s believed he began as a poor man, working on a plantation in America as an indentured servant. He escaped and became a buccaneer. During this period, he succeeded in establishing a fearsome reputation for himself, which is echoed even to this day. He is still often considered to be one of the most ruthless and barbaric pirates to have lived. The Spanish were often the victims of his cruelty, so he earned the nickname “Flail of the Spanish.” He would mercilessly kill everyone on board the ships he captured, tear out the tongues of prisoners, and is said to have eaten a Spanish soldier’s heart during one of his many attacks. His own death was, therefore, poetic justice. l'Olonnais and crew were shipwrecked on a sandbar off Panama. As they ventured onto land in search of food and water, a local tribe captured them and devoured them.

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Black Caesar: African Chief Turned Raider

Black Caesar and his friend, the sailor, turn to a life of piracy. (Noah Scalin / CC BY-SA 2.0)

While black pirates were not unusual, many of their names have been lost to history. One remembered to this day is Black Caesar (West African, ??? – 1718 AD), a legendary 18th-century AD African pirate. Originally from West Africa, Black Caesar was captured and sold into slavery. It is thought he may have been a chief. He is said to have been tall, strong, and intelligent. The ship he was imprisoned in sank off the coast of Florida, but he survived and began his career in piracy. He and his crew would pose as shipwrecked sailors and hail passing vessels for help. Once they were on board a ship, they would drop their disguise, rob the ship, and take the loot back to their hideout. In a disagreement about a woman, his partner and he had a duel, which Black Caesar won, killing his friend. Most sources claim that Black Caesar eventually joined the crew of another infamous pirate, Blackbeard. Eventually, Black Caesar’s reign of terror came to an end in 1718 AD, when he was convicted for piracy and hanged.

Black Bellamy: Robin Hood Of Pirates?

Black Bellamy was a famous pirate and also the richest pirate ever. (Allen & Ginter / CC0)

The notorious pirate “Black Sam” Bellamy (English, 1689 – 1717 AD) sailed the seven seas, plundering and pirating, becoming the richest buccaneer ever known. He was born in Devonshire, England, and in his late teens, he joined the British navy and fought in several battles. In 1716 AD, after a mutiny aboard a ship, he was named the new captain, and during just one year he and his crew robbed more than 50 ships in the Atlantic and the Caribbean, accumulating the equivalent to $120 million in today’s money, making him the richest pirate ever. Bellamy was also famous for his expensive clothes, especially black coats. As a captain, he was almost democratic, and the crew liked to call him “Pirate Robin Hood.” But this was no storybook ending – his pirate career was short-lived. In 1717 AD, he and his crew drowned when their ship was wrecked, and the 102 lost souls have recently been found buried in a secret location in Massachusetts. He was 28.

Grace O’Malley: The Irish Rover

Grace O’Malley was so successful that the Queen of England “let her go.” (Suzanne Mischyshyn / County Mayo - Westport House Grounds - Statue of Grace O'Malley)

Grace O’Malley (Irish, 1533 – 1603 AD) was born in Ireland around 1530 AD, the daughter of a wealthy nobleman and sea trader. Upon her father’s death, she inherited his large shipping and trading business. From her earliest days, she rejected the role of the 16th-century woman, instead embracing a life on the sea with her fleet of trading ships. The income from this business, as well as land inherited from her mother, enabled her to become rich and politically powerful. Grace commanded hundreds of men and some 20 ships in raids on rival clans and merchant ships. She also ran afoul of government officials, who made repeated attempts to curb her activity. At the age of 56, Grace O’Malley was finally captured, but she petitioned the Queen of England and successfully convinced her to release her and her family. She most likely died at Rockfleet Castle around 1603 AD.

Redbeard: The Barbarossa Brothers

Hayreddin Barbarossa: Redbeard, and his brothers, terrorized the Spanish and the Portuguese. (Public domain)

Hayreddin Barbarossa (Greek, c. 1466/1478-1546 AD) was one of the most notorious pirates of his day and one of the most successful naval commanders of the Ottoman Empire in the 16th century AD. Born on the Greek island of Lesbos around 1478 AD, he was originally known as Khizr. He had three brothers and they all became pirates and attained riches and fame by capturing European vessels in the Mediterranean Sea and preying on Spanish and Portuguese ships as independent corsairs. They conquered the North African city of Algiers and submitted it to the Ottomans as a means of protecting themselves from the Spanish. By 1518 AD, Hayreddin Barbarossa was the only one of the brothers left, as the others had all been killed during combat. Hayreddin not only inherited the rulership of Algiers, but also his brother’s nickname amongst the Europeans, “Barbarossa” (due to his red-colored beard). He continued to serve the Ottoman Empire loyally, and eventually retired to a villa on the northern shore of the Bosporus where he died of natural causes at the age of 68.

Blackbeard: The Wild Man Of The Sea

Blackbeard died young but his name lives on in films and the imaginations of so many writers. (Allen & Ginter / CC0)

There have been more successful pirates, but hardly more well-known than Blackbeard, even in modern times. Born Edward Teach (English, c. 1680- 1718 AD), Blackbeard intimidated enemies by barreling into battle with a wild persona; coiling smoking fuses into his long, braided beard, strapping multiple pistols and daggers across his chest, while clutching two swords. Capturing over 40 merchant ships in the Caribbean, he killed many prisoners and took numerous unofficial wives: one, a 16-year-old, he offered as a gift to his crew after she tried to reform him. He was finally captured and beheaded by the Royal Navy; his head raised upon a stake as a warning to other pirates off Virginia. He was approximately 35 when he died. Blackbeard was a central force during the “Golden Age of Piracy,” and books, plays, and movies would romanticize his story right up until today, including the now-iconic character Captain Jack Sparrow in Pirates of the Caribbean.

Sir Francis Drake: Pirate For Empire

Francis Drake: This famous pirate had a “license to steal,” granted by the Queen of England herself! (Daderot / CC0)

Known as “my pirate” by Queen Elizabeth I, Francis Drake (English, 1540-1596 AD) was a privateer (licensed pirate) for the English government. He sacked the Spanish army, his greatest foe, many times, and relentlessly plundered Spanish cities off the coast of Florida. He sailed his most famous voyage in 1577 AD and became the first English captain to circumnavigate the globe, while raiding ports and Spanish vessels loaded with treasure along the way. Queen Elizabeth knighted him immediately upon his return. He even rescued the failed English colonists of Roanoke Island, off the coast of the Carolinas, and brought them back to England. He also helped defeat the Spanish Armada. He survived all these adventures, and something as mundane as dysentery brought down this master privateer, killing him at age 56.

Ching Shih: From Prostitute To Pirate

Also known as Madame Cheng, Ching Shih ruled the South China Sea in her day. (Public domain)

Sometimes known as Madame Cheng (Chinese, 1775 – 1844 AD), Ching Shih was one of the most successful of pirates in history. Once a prostitute, upon the death of her pirate husband, she took over his entire “Red Flag Fleet” (so huge that it equaled all the combined fleets of all the other most successful pirates) and his pirate ways. She made her adopted son, Cheung Po Tsai, the captain of the fleet as well as her lover, and with his help, they robbed and taxed coastal towns. They attacked ships in the South China Sea, sparring with major nations, such as the British Empire, the Portuguese Empire, and the Qing dynasty. Her wealth and infamy grew. Ching Shih controlled more than 1,500 ships and 80,000 men. The Chinese government eventually offered universal pirate amnesty in exchange for peace; she accepted this and lived out the remainder of her years in charge of a casino and brothel. She died at age 69.

Top image: Famous pirates from around the globe who terrorized the seas for gold and glory.                  Source: waewkid / Adobe Stock

By Liz Leafloor