Meet Bartholomew Roberts, one of the most formidable pirates to ever sail the seven seas. He ravaged the seas, captured ship after ship, and terrorized the coasts of the Caribbean and Africa. After Henry Avery, he is credited with orchestrating the second-largest plunder in pirate history.
Born in Wales in 1682, Roberts was a boy deeply connected to the sea. He didn’t originally intend to become a pirate. He started his career as a legitimate seaman, working on merchant vessels and making an honest living. But life, as they say, often takes unexpected turns. In the 1700s, piracy was rampant across the Atlantic, the Caribbean, and along the African coasts. In 1719, while serving as the second mate on a slave ship called the Princess, his ship was captured by pirates in the Gulf of Guinea. The pirates were part of the crew of Howell Davis, also known as “Lucky Pirate.” Initially hesitant, Roberts was forced into a life of piracy.
From Reluctant Sailor to Ruthless Captain
The twist of fate came soon after. Howell Davis was killed in an ambush, and his crew needed a new captain. Despite having many experienced men among them, the crew unanimously chose Roberts. They saw in him a calm, intelligent, and natural-born leader. In June 1719, Bartholomew Roberts was declared captain.
Immediately, Roberts began treating piracy not just as a life of plunder, but as a business. He wasn’t a common marauder; he was a leader who implemented a strict code of conduct for his crew. He banned drinking, fighting, gambling, assaulting women, and leaving the ship without permission. He essentially created a set of by-laws for his pirate crew, establishing a kind of “corporate piracy.”
The Legendary Caribbean Heist
What truly cemented Roberts’s legendary status was a massive raid he led in the Caribbean in 1721. Operating near Porto Bello, his target was a Spanish convoy laden with gold and silver. Roberts first captured smaller ships, gathering intelligence on the convoy’s movements. Then, he launched his attack on the wealthiest fleet. That day, they captured a staggering 22 ships! They didn’t just take the ships; they emptied them of their treasures.
The haul was immense: an estimated 50,000 gold pieces and a massive amount of valuable goods. This was one of the biggest pirate raids of the era, worth an estimated $50 million in today’s money. After this epic heist, Roberts’s name, or rather his nickname, “Black Bart,” became a storm that swept across the Caribbean. Any ship that saw his flag in the distance would tremble with fear.
Roberts’s flag was also unique among pirates. Against a black background, it featured a skeleton or angelic figure holding an hourglass in one hand and a flaming sword in the other. These symbols represented both mortality and victory, sending a clear message: “You can fight and die, or you can surrender and let me celebrate. The choice is yours.” He understood brand marketing long before it was a thing.
Roberts plundered over 400 ships, a number that stands as one of the highest in pirate history. Famous pirates like Blackbeard were apprentices compared to him. Roberts’s “pirate code” was even adopted by many other crews, proving he was truly born for that world.
The Downfall of a Pirate King
In 1722, Roberts sailed from the Caribbean to the African coast. By now, the British Navy’s patience had worn thin. Bartholomew Roberts was no ordinary pirate; he had plundered hundreds of ships, wreaked havoc on countless colonies, and built a fleet that rivaled a small navy. Britain dispatched the warship HMS Swallow, captained by the seasoned seadog Chaloner Ogle, to hunt him down.
Off the coast of Cape Lopez, Roberts spotted the approaching warship. With his typical calm demeanor, he dismissed it as no cause for concern. But this overconfidence proved fatal. A cannon shot from the Swallow struck him directly while he was observing the ship through his spyglass. He died instantly. Following his final wishes, his crew threw his body into the sea to prevent the British from getting their hands on it. “My body shall never be hung from a yardarm of a warship,” he had vowed.
Bartholomew Roberts was more than just a pirate. He was a ruler of the seas, a terror to sailors, and one of the most enduring pirate legends in history.
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