Stede Bonnet
Nicknamed “The Gentleman Pirate” because he had been a wealthy plantation owner in Barbados and an army major before turning to piracy, Stede Bonnet (circa 1680 – 1718) earned his fame or infamy not because of his success as a pirate, but because of the remarkable incompetence, he displayed after taking up a career in piracy that he had no business pursuing, and probably should have left to roughnecks better suited to its travails and vicissitudes.
Born into a wealthy family of landed gentry, Bonnet had led a peaceful life for years, living 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.
As might be expected from a rich dilettante who took to piracy on a whim, Bonnet was not very good at it, and soon revealed himself an incompetent sailor and worse leader. He managed to seize only a few small and trifling prizes off the coasts of the Carolinas and Virginia, and only the fact that he paid his crew regular and generous wages – the only pirate captain to do so – kept them from deposing him and electing another captain in his stead.
He came across Blackbeard in Florida, who befriended Bonnet and persuaded him into giving up command of the Revenge because of his utter incompetence at piracy. Bonnet transferred to Blackbeard’s Queen Anne’s Revenge, where he remained as a guest. His own ship, Revenge, was taken over by one of Blackbeard’s lieutenants, whom the crew accepted as their new captain.
Soon thereafter, Bonnet accepted a royal pardon and a royal commission to go privateering against Spanish shipping. However, he decided to return to piracy in July 1718, and, hapless as ever, thought that adopting the alias “Captain Thomas” and changing the name of his ship to Royal James would suffice to mask his identity. It did not.
The following month, a British naval expedition came across Bonnet at anchor in the Cape Fear River estuary, and after a fight captured him and his crew. Bonnet managed to escape, but was recaptured after a few weeks on the lam, and taken to Charleston. There, he was tried and convicted on two counts of piracy, sentenced to death by hanging, and executed on December 10th, 1718.