Meet Bartholomew Roberts, The Most Successful Pirate Of All Time

Published February 22, 2018

Bartholomew Roberts may have been history's most polite pirate, but that didn't stop him from being the ultimate swashbuckling sailor of the high seas.

Bartholomew Roberts Sketch

Stringer/Getty ImagesA sketch of Captain Bartholomew Roberts in front of his two ships, The Royal Fortune and The Ranger, off the coast of Africa.

Captain Bartholomew Roberts was, in some ways, the archetypal pirate. Coasting under a black sail, he took more than 400 vessels in his career and strutted around in finery that Jack Sparrow would’ve envied.

At the same time, Roberts’ distaste for hedonism earned him the moniker “the Puritan Pirate.” He was a fascinating contradiction, and possibly the most successful buccaneer in the Golden Age of Piracy, whose idiosyncrasies have become so synonymous with swashbuckling that he allegedly inspired the character of The Dread Pirate Roberts in The Princess Bride.

Roberts’ career as a pirate leader began suddenly. After his captain, Howel Davis, died, Roberts was chosen as his successor — despite the fact that he had only been a pirate for six weeks.

His rapid promotion was even more shocking, considering he was a commoner. Born in 1682 in Wales, it’s thought that he took to the sea at 13 as a legitimate sailor. He eventually worked his way onto the slave ship, the Princess, captained by Abraham Plumb. It was the 1719 capture of this very ship off the coast of Africa that drafted him into a life of piracy.

He accepted the position as captain, allegedly grumbling “that since he had dipped his hands in muddy water, and must be a pyrate, it was better being a commander than a common man.”

Roberts’ looks may have contributed to his rapid ascent — he’s described in A General History of the Pyrates: From Their First Rise and Settlement in the Island of Providence, to the Present Time by Daniel Defoe as “… a tall black [i.e. dark complexioned] Man, near forty Years of Age … of good natural Parts, and personal Bravery, tho’ he apply’d them to such wicked Purposes.”

The Death Of Bartholomew Roberts

Hulton Archive/Getty ImagesThe death of Bartholomew Roberts off the coast of Gabon in west Africa.

His Rhett Butler-like physicality met a Captain Hook-esque fashion sense, featuring fine silks, a diamond-encrusted cross swinging from a gold chain, and a hat festooned with a red feather. He must have been an imposing sight in his finery, with his dark hair whipping in the sea breeze.

His outward decadence belied a soul of temperance. He lived by a code of rules and did not allow disorderly conduct, including gambling, excessive drinking, and female passengers.

His mix of striking charisma and moral rectitude served him well, as he bounced around the Atlantic from Africa to Brazil, up through the Caribbean to Canada, and back to Africa. In succession, he amassed a fleet including the boats Fortune, Royal Fortune, and Good Fortune.

He traveled on and with Fortune for years, until it ran out when he encountered the British warship Swallow in February 1722. The Swallow approached the Royal Fortune, and Roberts put off his interference until he was finished breakfasting.

When he was finally thoroughly concerned, he went above-deck to fight off the attackers, but his crew was too drunk to be of much good. The mostly-dry pirate was killed by grapeshot to the throat because his crew was intoxicated — perhaps the most tragicomic version of being hoist by one’s own petard in history.

Captain Roberts’ body was tossed overboard, and with the final splash went the Golden Age of Pirates — no buccaneer after him ever quite matched up.

Next, check out more real life pirates like Ching Shih, history’s fiercest female pirate, and Alexander Selkirk, the real-life Robinson Crusoe.

Andrew Milne
Andrew Milne holds a Bachelor's in journalism from Fordham University and his work has appeared on Bon Appétit and Food Network.
John Kuroski
John Kuroski is the editorial director of All That's Interesting. He graduated from New York University with a degree in history, earning a place in the Phi Alpha Theta honor society for history students. An editor at All That's Interesting since 2015, his areas of interest include modern history and true crime.