A Gentleman’s Legacy: Charleston in the Golden Age of Piracy

Jolly Roger of Stede Bonnet, the Gentleman Pirate. Each pirate captain had their own design for their Jolly Roger or pirate flags. The captain could be easily identified by the Jolly Roger flying from their mast.

During the Golden Age of Piracy, 1650 to 1720, thousands of pirates roved the seas. The Caribbean became a hotbed of piratical activities as swashbucklers were drawn to the heavily-laden, slow sailing Spanish galleons loaded with riches from the New World. Spanish galleons offered easy targets for pirate crews who were seeking wealth, and the Caribbean provided cover with a myriad of islands and coves perfect for smaller pirate vessels to use as shelter and bases of operations.

Caribbean towns welcomed pirates spending Spanish gold and silver. Given how far the West Indies are from Europe, it was difficult for European powers to patrol the Caribbean and control the pirate outbreak. All these factors—the increase in shipping of precious materials by the Spanish, the geography of the Caribbean, and the distance from Europe—created the perfect environment for piracy to take root and flourish.

Given the activities taking place just a few hundred miles south of the colony of South Carolina, it is not surprising pirates found their way to Charleston, often touted as the northernmost point of the Caribbean. Charleston’s harbor provided a welcome port for ships carrying goods from all over the world making it a perfect target for buccaneers.

The city understood the threat it faced from pirates, so Charlestonians deployed various tactics to protect the fledgling city. These precautions included the city wall, chevaux de frise, and harsh laws punishing anyone engaging in piracy in the city. Local tradition states that anyone convicted of piracy in Charleston was hanged at Shute’s Folly—the small sea island where Castle Pinckney sits today—with the bodies left hanging from the gallows serving as a warning to any and all who entered the port of Charleston that pirates were not welcome.

Chevaux de frise were spiked wrought iron pieces often affixed to gates or fences used to protect against intruders and were referred to as “pirate spikes”. Chevaux de frise continued to be used through the 19th century, long after the threat of piracy was gone.

Despite all of these attempts to protect the city, in 1718 Charleston fell victim to two of the most infamous pirates of the Golden Age. Edward Teach, better known as Blackbeard, and Stede Bonnet, the Gentleman Pirate, arrived outside of Charleston with a flotilla of ships used to create a blockade of the port. The people of Charleston were concerned the pirate fleet would turn on the city, plundering and pillaging—a reality that had occurred throughout the Caribbean and the Americas.

Unbeknownst to the people, the pirates had another objective in mind. During the blockade, Blackbeard and Bonnet successfully captured nine vessels including a ship carrying Samuel Wragg and his son. Samuel Wragg, the great uncle of Joseph Manigault, was a member of the Executive Council—exactly what Blackbeard was looking for. The pirates had not come to Charleston to attack the city; rather, they were looking for a specific prize and needed leverage to get it. The pirate crew was afflicted with what was likely syphilis, and they were in desperate need of medicine to treat the disease.

Blackbeard used Wragg and his son William, as well as other prisoners, as hostages bargaining their lives for the medicine he so urgently needed. Once the pirates procured the chest of medicine, the prisoners were released unharmed, but considerably lighter. The pirates pilfered the money and valuable items from each hostage leaving them almost naked as they arrived ashore.

Blackbeard and Bonnet promptly left Charleston and fled north to North Carolina where Blackbeard had a base of operations. At this time, the pirates separated ways and Bonnet procured a letter of marque from the governor of North Carolina legalizing his piracy as long as it was against Spanish vessels. However, Bonnet’s era of reform quickly came to an end as he continued to attack ships regardless of their nation of origin.

Engraving of Stede Bonnet from A General History of the Pyrates, 1724

Tales of Bonnet’s continued exploits made their way to Charleston where Governor Robert Johnson was still seething over the pirates’ successful exploitation of the city. Now trade routes were being disrupted between North and South Carolina bringing trade almost to a standstill. Believing enough was enough, Governor Johnson asked Colonel William Rhett to track down Bonnet and his crew and bring them back to Charleston to face justice.

William Rhett was a time-tested soldier-sailor who had a history of defending Charleston from naval attack. He immediately agreed to track down the pirate threat with two ships he outfitted with his own money. Rhett tracked Bonnet to the Cape Fear River. On September 27th, 1718, Bonnet and Rhett met ship to ship at what is now known as Bonnet’s Creek. After hours of fighting, Rhett’s men bested the pirate crew with losses on both sides. One of Rhett’s ships, the Henry, required extensive repairs delaying their return to Charleston.

Finally, on October 3rd, Rhett victoriously returned to Charleston towing Bonnet’s ship the Revenge now renamed the Royal James with twenty-nine pirate prisoners. Charleston did not have a public jail at the time, so Bonnet’s crew were jailed in the Guard House located at the Half-Moon Battery.

The Walled City of Charles Town. Number 3 marks the location of the Half Moon Battery where Bonnet and his crew were jailed. The Old Exchange Building is located on this site today.

Bonnet was not imprisoned with his crew, instead he was allowed to stay at a house under guard. Bonnet’s treatment stemmed directly from his social status before turning pirate. He was a gentleman born to a wealthy planter elite family in Barbados but had chosen a life of piracy over the comfortable life. It is unclear exactly what caused this drastic change, likely it was the choice of a man who was bored with his life and desired excitement like the lives of the pirates he read about including Blackbeard.

Whatever led Bonnet to the pirate’s life, it is unlikely he expected it to end like it did. Realizing the harsh reality that he was facing, Bonnet decided to flee his imprisonment in a desperate attempt to save his life. Dressing in women’s clothing, Stede Bonnet disguised himself and slipped from the house of his captivity and fled. He made it to Sullivan’s Island before authorities recaptured him. He did not return to his lavish prison, but instead was thrown into the jail with his crew.

Bonnet and his crew were tried in a series of individual cases under Judge Nicholas Trott who clarified the legal definition of piracy as “Robbery committed upon the Sea, and a Pirate is a Sea-Thief.” In addition to his acts of pirating, Bonnet was also condemned for leading other less-educated and impoverished men into a life of crime.

In his defense, Bonnet claimed he never gave any orders to attack any vessels, blaming his crew and Blackbeard for any acts of piracy he was accused of doing. He even went so far as to claim he was asleep when his crew captured a sloop called the Francis. Despite his best efforts, Bonnet was convicted of piracy and sentenced to be hanged.

In one last effort to avoid the noose, Bonnet penned a letter to Governor Johnson pleading for his life. Unsurprisingly, Governor Johnson denied his request for clemency.

On December 10, 1718, Stede Bonnet’s career of piracy ended a little less than two years after it started. Bonnet and his crew were executed at White Point (today’s White Point Garden) near the original walled city of Charleston. The bodies were left hanging in the gallows for three days to serve as a warning to all who entered the port of Charleston.

This marker was placed by the Charleston Historical Commission in 1943 to document the execution of Stede Bonnet, his crew, and other pirates at White Point.

Learn more about pirates in Charleston by visiting the Lowcountry History Hall and get hands-on with the pirate life in Kidstory!

Elise Reagan
Chief of Education

 

Select Bibliography:

  • Johnson, Charles. 1726. A General History of the Pyrates,. London, T. Woodward.
  • The Tryals of Major Stede Bonnet, and other Pirates. 1719.