Yo ho, yo ho, a pirate’s life for me!

　　From 1650 to 1720, a seventy year period known as the Golden Age of piracy, this chantey was sung by looting and murderous pirates sailing the seven seas. While not every buccaneer was a cutthroat swashbuckler, there are a handful of individuals who were downright the nastiest people of their age. From the infamous Blackbeard to the lesser-known Ching Shih, the following seven pirates were not your average Halloween costume.

　　

7. Barbarossa Brothers

The Barbarossa Brothers, Aruj and Hizir, were born on the Greek island of Lesbos, which at the time, was ruled by the Ottoman Empire. They accumulated great riches in their early career as pirates, raiding European sailing vessels throughout the Mediterranean. In 1516, the Ottoman sultan instructed Aruj to set up a base along the Barbary Coast to prevent the Spanish and Portuguese from taking control of North Africa. After the eldest brother was killed in battle two years later, Hizir took over, spending the remainder of his life fighting Christian enemies, including a specialized fleet created by the pope to bring an end to his power in that part of the world. Hizir retired from piracy in 1545, dying at Constantinople the following year.

　　

6. Black Bart

Bartholomew Roberts with his ship and captured merchant ships in the background. Image credit: Engraved by Benjamin Cole (1695–1766)/Public domain Active during the Golden Age of piracy, Bartholomew Roberts—also known as Black Bart—is often regarded as the most successful swashbucklers to roam the Caribbean. Roberts was working aboard a slave ship when he was kidnapped by pirates. Within six weeks, he was elected as the new captain after the previous one perished. His first victory was the capture of a Portuguese treasure vessel, which he managed to loot under the entire enemy fleet’s nose. Commanding a fleet of four ships himself, he would go on to capture 470 sailing vessels in his four year career, more than the combined amount of his contemporaries. Roberts quickly developed a reputation for being cruel and cold-blooded toward his victims, but having started life among the lower ranks of society, he treated his own crew with care and respect. He died in 1722 by grapeshot while engaged with the Royal Navy.

　　

5. Blackbeard

Edward Teach's severed head hangs from Maynard's bowsprit, as pictured in Charles Elles's The Pirates Own Book (1837). Perhaps the most famous pirate on this list, Edward Teach ruled the Caribbean from 1716 to 1718. After a short stint as a privateer, he joined the crew of Benjamin Hornigold, who taught him all about piracy. When his mentor retired in 1717, Teach captured a French slave ship, refitted it with forty cannons, and dubbed it his flagship under the name Queen Anne’s Revenge. Throughout the following year, he developed a horrific reputation. As an intimidation tactic, he surrounded himself with smoke created by lit fuses placed in his facial hair, hence the name: Blackbeard. He always carried an arsenal of knives, cutlasses, and pistols as if they were everyday accessories. Some rumors claim he was even involved in voodoo and black magic. Teach accepted a royal pardon in 1718, but soon returned to piracy. Engaged in a battle with the Royal Navy, it took twenty stab wounds and five gunshots to take the feared pirate down.

　　

4. Ching Shih

Ching Shih was a daring and infamous female pirate. Ching Shih was a sex worker in a Cantonese brothel when she met pirate Zheng Yi in 1801. Together, they ran the Red Flag Fleet, expanding it from 200 to 1,800 ships. When Zheng Yi died in 1807, Ching Shih took full control of the fleet and created her own set of laws under which her crew was bound. Such laws were established to maintain order and to protect their female captives. Dubbed the Terror of South China, she was known for her dramatic punishments, which included nailing offenders to the deck of her ship. She was a looter and a thief, but some sources claim she was also an opium smuggler. Ching Shih’s power was so great that the Chinese government offered her amnesty just to eliminate her growing influence. After negotiating to keep all her treasure, she retired from piracy and opened her own gambling house. Ching Shih died in 1844.

　　

3. Edward Low

Edward Low, Torturing a Yankee, from the Pirates of the Spanish Main series (N19) for Allen & Ginter. Born to a poor family, Londoner Edward Low quickly turned to a life of crime. As an adult, he left for America where he eventually found himself as the captain of a ship. After journeying to the Caribbean, Low and his crew sailed about capturing vessels, with one fishing schooner becoming his flagship The Fancy. It did not take long for Low to develop a nasty reputation for being violent and excessively cruel. On one occasion, he cut off a captain’s lips and fed them to him before massacring his entire crew. By 1723, the Caribbean authorities had enough of Low. His fleet was defeated by the warship HMS Greyhound, but The Fancy escaped. Low grew harsher toward his crew and soon found himself mutinied against and marooned. Rumor has it the French picked him up and hanged him in Martinique.

　　

2. François l’Olonnais

François l'Olonnais from "De Americaensche Zeerovers". Getting his start in 1660, François l’Olonnais’s career lasted just shy of ten years. Because he always killed every member aboard his captured ships, the Frenchman developed a reputation for being one of the most ruthless pirates in the Caribbean. His methods of extracting information were extreme; he once ate a human heart to instill terror in his prisoners who quickly revealed unguarded routes to a gold mine. He was particularly feared among the Spanish, whom he hated with a fiery intensity. L’Olonnais was eventually captured by the native Kuna tribe somewhere in the Gulf of Darien. Torn to pieces and tossed into a fire, he was a violent man who met a violent end.

　　

1. William Kidd

Captain Kidd in New York Harbor, in a c. 1920 painting by Jean Leon Gerome Ferris Captain William Kidd began his career as a Scottish privateer working for the British government. In 1695, he set off to hunt down pirates in the Indian Ocean. When half his crew was taken away by a Royal Navy captain who was upset by the Scotsman’s failure to salute him, Kidd was forced to hire a crew of former pirates and criminals in New York. Once they reached the Indian Ocean, Kidd was unable to locate any pirates. Facing failure, his crew urged him to attack a passing vessel. He gave in and got his first taste of piracy. Kidd continued to loot various ships, but he was not officially declared a pirate until he attacked a British East India Company ship in 1698. He was eventually arrested and sent back to London where he was hanged in 1701. His body was put on display along the Thames as a warning to all other pirates.