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.