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Stede Bonnet May Have Been the World's Worst Pirate

He wasn't exactly fearsome.

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  • Depiction of Stede Bonnet's surrender from c. 1888.Photo Credit: Wikipedia

The Golden Age of Piracy gave rise to legendary outlaws that have been immortalized and fictionalized in the centuries since they prowled the waters of the Caribbean. We have Black Bart and his ruthlessly efficient plundering, Charles Vane and his fearsome bouts of violence, and Benjamin Hornigold and the Republic of Pirates. 

Most infamous of all was Blackbeard, a menacing mountain of a man who supposedly put slow-burning strands of rope in his hair to shroud himself in a cloud of smoke. One of Blackbeard’s associates, Stede Bonnet, would enter the history books for a different reason, however: some call him “The Gentleman Pirate”, while others call him the worst pirate of the entire Golden Age.

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Stede Bonnet’s background and upbringing would be considered unique among pirates. Pirates of this age were typically criminals, vagrants, or impoverished sailors who knew no other life. Many were forcibly captured by press gangs back on the British Isles and conscripted into the Royal Navy, which they would desert once they reached the Caribbean and subsequently take up piracy for food and shelter. Escaped slaves were also known to be taken in by pirate crews. The result was that piracy became synonymous with class warfare and politics. Some common folk saw them as Robin Hood-esque vigilantes that fought against the wealthy merchants of the waves, or subversive leaders who contributed to revolutionary causes against unpopular kings.

Not Bonnet. Bonnet was born in Barbados to a wealthy English family, where he received an education and inherited the family sugar plantation at a young age after the death of his father. Bonnet was raised as a gentleman and groomed to be a landowner, married well at the age of 21, and was a Major in the Barbadian militia. He had become such a distinguished and well-respected member of Barbadian society that in 1716 Bonnet was made a Justice of the Peace. 

Then something happened. Bonnet told his family and friends that he would be taking a trip away from Barbados. He finalized some paperwork that handed over control of his affairs to his wife and friends while he was away. On the side, however, Bonnet had secretly purchased a sloop and was gearing up for his new career: piracy.

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  • A print engraving of Stede Bonnet from A General History of the Pyrates, c. 1725.

    Photo Credit: Wikipedia

No one is exactly sure why a wealthy, respected plantation owner wanted to leave his cushy life and family behind for the rugged open seas. Rumor has it that marital problems were a contributor; but perhaps he was just bored with life, having little to do beyond watch over the estate where he had lived for most of his life. 

Others suggest Bonnet had debtors, or experienced some sort of mental break after the death of one of his children. He could have also been fueled by politics, as he may have been a Jacobite opposed to the reign of King George I, which was a common stance among English pirates. Whatever the reason, Bonnet had purchased the 10-gun sloop named Revenge, even though most pirates stole their first ship.

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Bonnet had no knowledge of sailing, piracy, or how to lead a crew of buccaneers, but he paid his crew of 70 men a salary and that was enough for them. The Revenge captured a few ships around Virginia and the Carolinas, largely thanks to the skill of his experienced crew. When sailing for Nassau, home of the Republic of Pirates—a loose confederation of the seafaring outlaws—Bonnet encountered a Spanish man-o-war, one of the fiercest ships on the waves. 

Bonnet decided to attack, despite being heavily outgunned and outmanned. The fight went as you would expect: half of the crew on the Revenge were killed or wounded, and Bonnet himself was seriously injured. They managed to escape, but the situation was grim. Some of the ships they encountered along the Americas had to be scrapped to repair the Revenge.

At some point, they came upon a legendary pirate ship: the Queen Anne’s Revenge, captained by none other than Edward Teach, better known as Blackbeard. Bonnet was thrilled to meet such a notorious pirate, and Teach was initially impressed by Bonnet’s good manners and pleasant demeanor. The two pirate captains agreed to sail together. 

Soon, however, it became clear to Blackbeard that his new companion was a complete rookie, and it didn’t take long for the infamous pirate to hatch a scheme. Bonnet was persuaded to give up command of the Revenge and live as a pampered guest on the Queen Anne’s Revenge instead. Bonnet’s crew actually welcomed the change, though the Barbadian found himself more of a prisoner than a guest.

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Blackbeard and Bonnet plundered the Americas for around two weeks, until Bonnet was reinstated to the Revenge, as Blackbeard announced he was heading to North Carolina to receive a royal pardon. Bonnet wished to do the same, and went on land to receive a pardon of his own. When he returned, he found his ship stripped of all booty, with just a couple dozen marooned sailors left. Blackbeard was long gone.

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  • A monument to Stede Bonnet in Charleston, South Carolina.

    Photo Credit: Wikipedia

Though he had just received a pardon, Bonnet took up piracy again not long after this incident. Something had changed in him. Now he was truly out for vengeance—though ironically, he now decided to change the name of his ship from Revenge to Royal James

Bonnet ditched his gentlemanly ways, killing prisoners, abusing crewmen, and threatening civilians. He certainly seemed to have learned something in his time with Blackbeard. When he plundered a ship near Charleston, around the same time that the pirate Charles Vane was terrorizing the area, the governor sent out a pirate hunter. A protracted battle ensued, during which Bonnet declared he would rather blow himself up than surrender, but his crew overruled him. Bonnet was captured and put into house arrest because of his former status as a gentleman.

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A written appeal to the governor and a brief escape from his house arrest did little to deter his impending fate. His trial was long, much longer than his crewmates, as Bonnet gave a detailed account of his time with Blackbeard, whom he blamed for anything and everything. But his testimony was to no avail. 

On December 10, 1718, Bonnet was hanged. He had been a pirate for less than two years. He leaves behind an odd little legacy of a naive, wealthy gentleman who bought his way into piracy and encountered the most fearsome pirate on the seas. Though he never got his revenge against Blackbeard, he could take some solace in the knowledge that his former colleague perished a month before he himself made it to the gallows.