History’s Most Famous Pirates

Shrouded in lore and mystique, pirates built a fierce reputation upon their swashbuckling adventures that took place upon the high seas. They regularly raided and took over merchant ships, pillaged and plundered every chance they got, and enjoyed a free-spirited lifestyle that included plenty of partying and good times. However, things didn’t always go as planned and countless pirates died because of their chosen profession, and everything from illness to battle posed a threat to their existence. Although their success was sometimes short-lived, the appeal of a free-roaming pirate’s lifestyle is something that is still lusted after by many people to this day. Let’s take a closer look at the stories of some of history’s most famous pirates:

Edward Teach (aka “Blackbeard”), 1680-1718

Perhaps the most famous pirate of all time, Blackbeard definitely lived up to his fearsome reputation. He was said to enter into every battle with a bevy of weapons including knives, pistols and two swords. At his most powerful, he had four ships in his fleet and 300 loyal pirates to man them. He seized more than forty merchant ships in the Caribbean and ruthlessly killed several of his prisoners. While he had an impressive run, his luck ran out when he was captured by the Royal Navy and beheaded, with his severed head raised near Virginia’s Hampton River to warn other pirates to stay away.

Anne Bonny, 1700-unknown

Although she got a new start by moving with her family from Ireland to Nassau, she ended up in an unhappy marriage that led Bonny to look for excitement in other places. She certainly found it when she met “Calico Jack” Rackham, who happened to be the captain of a pirate ship. Because women were generally unwelcome as part of the crew, she dressed and behaved like a man to fit in and kept up by fighting and drinking with the boys. She encouraged violence and bloodshed among the crew and was eventually captured and sentenced to death but escaped by claiming she pregnant. It is unknown where her life took her after she was freed.

Sir Henry Morgan, 1635-1688

Quietly backed by England, Captain Morgan made a name for himself by successfully leading a Jamaican fleet that disrupted Spain’s power in the Caribbean. While it is rumored that he might have terrorized as many as four hundred ships during his career, his most impressive accomplishment was raiding affluent Panama City with thirty ships and 1,200 men, yielding vast riches. Although he was arrested and taken to England after his great plunder, he was knighted by the king and released to hold the title of deputy governor in Jamaica, where he lived out the rest of his life as a plantation owner. 

Bartholomew Roberts (aka “Black Bart”), 1682-1722

Although he was initially forced into piracy while aboard a captured ship, Roberts embraced his new role and happened to be a natural leader possessing a winning combination of traits including charisma, bravery, a sense of adventure, and impressive navigational skills. His crew was loyal to a fault as he led them to plunder more than 400 ships, an unprecedented number. His death, which occurred in battle against a British captain, devastated his faithful crew and other supporters.

Henry Every (aka “Long Ben”), 1653-unknown

His once-legitimate career as a sailor for the British Royal Navy turned into piracy through mutiny, upon which he built a reputation as one of the most intimidating and successful pirates to terrorize the Red Sea and Indian Ocean. While the number of ships he overtook was modest, the few he captured were filled with astounding treasures including jewels and gold which made him the richest pirate in his day. He soon gave up piracy and went under the radar as he was a very wanted man, although there is no record that he was ever found.