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The Real Pirates of the Caribbean

Khalid Elhassan January 7, 2020 32 min

3. The Sad Sack Pirate

Stede Bonnet (circa 1680 – 1718), nicknamed “The Gentleman Pirate” because he had been a wealthy plantation owner in Barbados and an army major, made a terrible career choice in turning to piracy. He became famous not because of his success as a pirate, but because of the remarkable incompetence, he displayed after taking up a career he probably should have left to roughnecks better suited to its travails and vicissitudes.

Born into a wealthy family of landed gentry, Bonnet led a peaceful life for years with his wife in a profitable Barbadian sugar plantation. Then out of the blue in 1717, in some type of mid life crisis, he decided to escape marital difficulties and boredom at home by purchasing a ship, naming it the Revenge and outfitting it with cannons. Hiring a crew of 70 sailors, he then sailed off into the deep blue to become a pirate.

Written by

Khalid Elhassan

A lifelong history buff, I developed a particular passion for WW2 history as a child, when I spent hours listening to my grandfather, enraptured, as he recounted his wartime experiences in the British East African Campaign and with the British 8th Army in North Africa.

I graduated with a history BA from George Mason University, then went on to get a JD from the University of Virginia School of Law. After lawyering for a decade, I moved to sunny Rio de Janeiro and a less demanding career, opening a tourism agency in Copacabana.

A big chunk of my free time is spent blogging (you can follow me on Quora https://www.quora.com/profile/Khalid-Elhassan ) or freelance writing, mostly about my favorite subject, history.