Most pirates limped into debt, disease, and a short lifespan. But a few broke through with staggering hauls that would make hedge fund managers envious. These men, often part privateer and part outlaw, struck treasure at sea and rewrote the rules of risk and reward. Here’s a look at the 15 highest-earning pirates in history.
Black Sam Bellamy, $120 Million
He called himself the “Robin Hood of the Sea,” and for a short time, he lived up to it. Bellamy captured over 50 ships in just one year, including the Whydah Gally, loaded with gold, silver, and rum. Sadly, his flagship went down in a storm off Cape Cod.
Sir Francis Drake, $115 Million
Though knighted and celebrated as a hero, Sir Francis Drake made his fortune plundering Spanish holdings in the name of the Crown. His 16th-century expeditions were backed by Queen Elizabeth I and earned him an estimated $170 million in today’s money.
Thomas Tew, $103 Million
Tew started with a letter of marque but turned rogue quickly. His biggest payday came when he captured an Indian ship with gold, silver, ivory, and silk. That prize alone was worth tens of millions. Tew’s career was cut short by a cannonball, but not before he amassed over $140 million.
Bartholomew Roberts, $32 Million
Known as Black Bart, Roberts was ruthless and efficient. He enforced a strict pirate code and operated from West Africa to the Caribbean. His tactics paid off, but he met his end in battle, injured through the throat by grapeshot in 1722, and his fortune vanished with him.
Jean Fleury, $31.5 Million
Fleury was one of the first pirates to hit it big. In 1523, he captured two Spanish galleons carrying Aztec treasure looted by Hernán Cortés. The score was massive—estimated at over $47 million today. His luck ran out when the Spanish caught him just four years later.
Henry Morgan, $13 Million
Morgan made his money raiding Spanish settlements across the Caribbean. His biggest score came from sacking Panama City with minimal losses. Later, he was rewarded with knighthood and land in Jamaica. His lifetime haul was around $19.6 million in modern value, much of it earned before he turned respectable.
Blackbeard (Edward Teach), $12.5 Million
Edward Teach, better known as Blackbeard, built a reputation on menace. He tangled slow-burning fuses into his beard, terrorizing his enemies before boarding. He also captured dozens of ships and ruled parts of the Atlantic.
John Bowen, $40 Million
Bowen kept things quiet but profitable in the Indian Ocean. He had a knack for targeting rich merchant vessels and stashing away gold without drawing too much heat. By the time a disease took him in 1704, he’d banked around $40 million.
Thomas White, $16 Million
After escaping slavery, White turned to piracy and quickly rose in stature. He gained a reputation for being fair, which helped him keep loyal crews. He operated near Madagascar until natural causes took him, and his crew buried him with full honors.
John Halsey, $13 Million
Halsey blurred the lines between pirate and privateer, as he took down merchant vessels from Europe and Asia. He was known to negotiate well and avoid unnecessary bloodshed. Before acquiring a tropical disease, he amassed much wealth through well-chosen targets.
Francois Le Clerc, $7.5 Million
Known as “Jambe de Bois” (Peg Leg), Le Clerc terrorized the Caribbean in the 1500s. He famously looted Santiago de Cuba and Portuguese ships returning from the Americas. Despite his disability, he was aggressive and successful.
Edward England, $8 Million
England is remembered for its unusual streak of mercy. He sometimes let defeated crews go free and avoided unnecessary cruelty. But his softer edge didn’t stop him from earning big. His downfall came at the hands of his men, who thought him too lenient and marooned him.
Stede Bonnet, $4.5 Million
As a former landowner with no seafaring experience, Bonnet took to piracy out of boredom—or possibly a midlife crisis. He bought a ship, hired a crew, and eventually teamed up with Blackbeard. However, things unraveled quickly, and he was captured in 1718.
Richard Worley, $3.5 Million
Worley went from deckhand to captain almost overnight during a brutal takeover. He raided ships off the Carolina coast and managed a few notable captures. His run ended less than a year later when colonial forces cornered and ended his fate.
Howell Davis, $3.5 Million
Howell Davis pulled off several heists by pretending to be a royal envoy or merchant and slipping past defenses with charm. His smooth deception earned him ships and cargo. But clever words only go so far—he fell in 1719 after a failed trick on a Portuguese fort.