When you think of piracy, names like Blackbeard and Calico Jack immediately spring to mind. Yet there exists a shadowy roster of seafarers who never earned the Hollywood spotlight but still managed to carve out impressive legacies. In this roundup we present ten obscure yet successful pirates, each a fascinating blend of grit, cunning, and sheer audacity.
10 Obscure Yet Pirates You Should Know
10 Pier Gerlofs Donia “Big Pier”
Pier Gerlofs Donia, a burly 15th‑century farmer from the Frisian town that now lies within the Netherlands, turned to piracy after his home was sacked and his wife assaulted. Towering and muscular, he earned the nickname “Big Pier.” He organized a militia called the Arumer Black Heap and waged a relentless guerrilla war against the Holy Roman Empire. Whenever he captured a suspect, he forced them to recite the tongue‑twisting phrase Bûter, brea en griene tsiis: wa’t dat net sizze kin, is gjin oprjochte Fries – roughly “Butter, bread, and green cheese: if you can’t say that, you’re not a true Frisian.” The phrase proved difficult for Dutch or German tongues to manage.
On land Donia was a terror wielding a massive Zweihander greatsword that reportedly stretched over two metres (seven feet). At sea he proved equally shrewd, seizing roughly a hundred vessels for the “Cross of the Dutchman.” Many of those merchant ships were refitted as troop transports, swelling his army’s mobility. Although his original aim was Frisian independence, internal squabbles eventually drove him away from the cause. By 1519, after barely four years of conflict, Donia retired to a quiet life, slipping away in his sleep the following year.
9 Cornelis Jol “Pegleg”
Cornelis Jol, affectionately called “Houtebeen” (Dutch for Pegleg), lost his leg to a cannonball as a boy. A 17th‑century Dutch corsair, he concentrated his raids on Spanish vessels in the West Indies after serving in the Dutch navy and joining the West India Company in 1638.
More a privateer than a full‑blown pirate, Jol became a folk hero in the Netherlands for his role in turning the tide against Spanish and Portuguese forces in the New World. The Spanish even sang a mocking song about him that began, “Peg‑leg is a bad pirate, who eats raw octopus and drinks sea water.” His wooden leg made him one of the earliest captains known for such a prosthetic, cementing his place in nautical lore.
8 Jean Lafitte
Jean Lafitte, a French‑born buccaneer, launched his career just after the turn of the 19th century, prowling the Gulf of Mexico under the unrecognised flag of Cartagena, a Colombian city that had declared independence. He also operated as a smuggler, moving contraband and slaves into the United States. Though he blamed American policies for his turn to crime, Lafitte fought alongside the U.S. against the British during the War of 1812.
The British first tried to recruit him, but Lafitte feigned cooperation while feeding them false intelligence. He later approached the American government, offering his services in exchange for pardons for himself and his crew. The U.S. accepted, and many of his men settled into respectable lives after the war. Yet Lafitte could not stay ashore; he resumed piracy near Texas until around 1820, and the circumstances of his death remain a mystery.
7 Laurens de Graaf
Laurens de Graaf, another 17th‑century Dutch marauder, earned the reputation of a gentleman outlaw. He was known to travel with violins or trumpets, which he would play for his crew during long voyages. After a respectable stint as a sailor, a loss of employment and a subsequent capture by pirates pushed him over the edge.
Accounts of his early life differ—some claim he was a Spanish prisoner or slave sent to the Americas as punishment. Regardless, de Graaf ended up in the West Indies, where he seized the famed Tigre, a captured 24‑gun Spanish man‑of‑war. For decades he raided Spanish and English outposts across the Gulf of Mexico and beyond. Despite numerous pirate hunters on his trail, he evaded capture and eventually retired to the southern United States, where he is believed to have died.
6 Roberto Cofresi “El Pirata Cofresi”
Roberto Cofresi, a celebrated figure in Puerto Rico, operated as a pirate during the 19th century. Initially a merchant sailor, he turned to piracy in his twenties due to severe economic hardship on his island. Early on he targeted American vessels, especially those transporting gold.
Because the island remained under Spanish rule, colonial authorities largely ignored his activities, even when the United States pressed for his capture. As Spanish oppression of native Puerto Ricans intensified, Cofresi broadened his list of victims to include Spanish ships, earning the ire of the crown. He built a complex network of contacts that helped him evade capture for years, and his Robin‑Hood‑like reputation endeared him to the public. In 1825 his luck ran out; Cofresi and eleven of his men were executed.
5 François l’Olonnais “The Bane Of The Spanish”
Born Jean‑David Nau, the French privateer later known as François l’Olonnais harbored an all‑consuming hatred for Spain after serving as an indentured servant to Caribbean Spaniards. Once freed, his fury manifested in a ferocious campaign against Spanish interests throughout the 17th century.
L’Olonnais was notorious for extreme cruelty—legend tells of him dissecting a prisoner, biting the heart, and hurling it at a companion. His most celebrated feat was the swift capture of the supposedly impregnable Venezuelan town of Maracaibo, whose 16‑gun fort had long been deemed unassailable. Using brilliant tactics, he overran the fort in a matter of hours. He then terrorised the town’s inhabitants until they revealed hidden treasure. After a later shipwreck on the coast of Cartagena, he met his demise on the island of Darien, where indigenous inhabitants tore him apart limb by limb.
4 Rahmah ibn Jabir “The Scourge Of The Pirate Coast”
Rahmah ibn Jabir, a Bahraini corsair who thrived at the turn of the 19th century, earned the moniker “The Scourge Of The Pirate Coast.” His clan, Al Jalahma, had been locked in a two‑decade feud with the rival Al Khalifah clan, a rivalry that fueled much of his piratical activity.
By deliberately sparing British ships, ibn Jabir avoided provoking the Crown, focusing his aggression on Al Khalifah and other regional powers. At his zenith, nearly two thousand men—many of them freed African slaves—served under his banner. He endured severe injuries, losing an eye and most use of his right arm. His ruthless reputation eventually united Arab forces against him, and in 1820 he was finally defeated. Refusing to be captured by his enemies, he detonated barrels of gunpowder aboard his vessel alongside his eight‑year‑old son, ending his life and that of his crew in a fiery finale.
3 Olivier Levasseur “The Buzzard”
Olivier Levasseur, better known as “La Buse” (the French for “The Buzzard”), prowled the Caribbean in the early 18th century before shifting his operations to the Indian Ocean. His nickname reflected the speed and ferocity with which he struck his foes.
After being cast out by fellow buccaneers, Levasseur captured the crippled Portuguese vessel Nossa Senhora del Cabo near Réunion Island in 1721. The ship was laden with untold riches and valuable religious relics. The French authorities, alarmed by his growing power, finally apprehended him. He was tried, sentenced, and hanged. In his final moments, he tossed a mysterious necklace and cryptic papers into the crowd, challenging anyone to locate his hidden treasure—a bounty that remains unfound to this day.
2 Samuel Bellamy “Black Sam”
Samuel Bellamy’s pirate career was astonishingly brief—barely a year or two—but it was spectacularly lucrative. Dubbed “Black Sam,” he amassed an estimated $120 million in modern dollars, making him the wealthiest pirate on record.
Initially a treasure hunter who came up empty‑handed, Bellamy turned to piracy, eventually securing a ship and a loyal crew. He governed his vessel with a quasi‑democratic system that earned him the devotion of his men. Known for his mercy toward captured sailors, he led his “Robin’s Hood Men” to seize over fifty ships across the Caribbean and Atlantic. His crowning achievement was the capture of the English slave ship Whydah, brimming with over 20,000 pounds sterling. The crew set sail for Massachusetts, only to be wrecked by a ferocious storm that sank the Whydah, sparing just two survivors.
1 Aruj “Redbeard”
Aruj, born in the 1470s to a Turkish father and Greek mother on the island of Lesbos, endured brutal oppression at the hands of the Knights of Saint John. After three years of enslavement, he escaped with a burning desire for vengeance. Together with his brother Hizir, he became a feared Mediterranean raider, initially serving as a privateer for Egyptian interests.
During a siege of a Spanish‑captured port, Aruj suffered a severe arm injury that required amputation. Both brothers earned the nickname “Barbarossa,” meaning “Redbeard,” due to their striking hair color. Their piracy made them among the richest men of the era. After numerous clashes with Spanish and even Muslim fleets, Aruj fell in battle, leaving his fortune to his brother. One of his most audacious acts was the capture of the Pope’s own trading galley off the coast of Elba.