Wicked Charleston: The Dark Side of the Holy City

Wicked Charleston: The Dark Side of the Holy City

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by Mark R. Jones

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A beautiful Southern city distinguished by its opulent homes, towering church steeples and hospitality, Charleston, South Carolina, has long been associated with the genteel side of Southern living. However, beyond the outward appearances that most people associate with Charleston, there is another side that most visitors and residents would dare not believe is


A beautiful Southern city distinguished by its opulent homes, towering church steeples and hospitality, Charleston, South Carolina, has long been associated with the genteel side of Southern living. However, beyond the outward appearances that most people associate with Charleston, there is another side that most visitors and residents would dare not believe is part of the very fabric from which the city's history was woven. Wicked Charleston: The Dark Side of the Holy City, by local resident and tour guide Mark R. Jones, opens the door to the dark alleys and seedy characters not often associated with the Charleston of today. From the sexual escapades of an original Lord Proprietor and the comings and goings of the most notorious pirates, to secret brothels and nightclubs, Jones leads the reader back to a time when drinking, eating and whoring with more than fifty wenches" was perhaps more common in the Holy City than one may imagine."

Product Details

History Press, The
Publication date:
Wicked Series
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Product dimensions:
6.00(w) x 9.20(h) x 0.60(d)

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Chapter Two: The Sweet Trade and Free Love

"If you had fought like a man, you wouldn't have to be hanged like a dog."

Female pirate Anne Bonny to her partner Jack Rackham.

The Odd Couple: Blackbeard and Stede Bonnet

Pirates were once encouraged in Charles Town. During the first two decades of the eighteenth century pirates preyed on the Spanish galleons carrying gold and other treasure from Florida to Spain. Charles Town tavern owners and shopkeepers embraced those free-spending agents of the sweet trade. However, after 1718 there was an increase of attacks on British ships bound to and from Charles Town, plundering by the likes of Blackbeard, Charles Vane, Calico Jack Rackham and the "gentleman" pirate Stede Bonnet.

Bonnet was an unlikely candidate for piracy. He was an educated man and served in the Royal Army as a major. After retirement from the military, he grew wealthy as the owner of a large sugarcane plantation in Barbados. For some reason, in 1717 Bonnet purchased a ship, the Revenge, hired a crew of seventy and set sail out of Bridgetown Harbor and began to plunder ships in the Caribbean. This is the only recorded incident of a pirate purchasing a ship.

No one is sure why Bonnet turned to piracy. One theory is that he suffered from a "disordered mind." Another theory is that he rebelled against his comfortable life and suffered what we would now call a "midlife crisis." Instead of buying a Corvette, he bought a pirate ship. The most enduring and popular theory, however, was that Bonnet turned to the sweet trade to escape his nagging, shrewish wife.

It didn't take Bonnet's crew long to determine that he was not much of a pirate. He suffered fromseasickness, dressed in fine clothes and wore a powdered wig. He was a refined gentleman who rarely drank and spent most of his time reading in his cabin. That was not the profile of a typical pirate. The crew was talking mutiny with plans to strand Bonnet on a deserted island until the Revenge crossed paths with the infamous Edward Teach-"Blackbeard."

Blackbeard was born in Bristol, England around 1690. When he was twelve he served as a deckhand aboard a privateer during Queen Anne's War (1702-1713). There was a thin line between being a privateer and a pirate; the only thing that separated the two was a sheet of paper that bore the queen's signature. As a privateer, one had the right to attack enemy ships and, in the name of the queen, seize their cargo called "booty." When there was no war in which they could offer their services, many privateers became pirates.

Blackbeard arrived in Jamaica as a teenager and for the next several years he served his pirate apprenticeship under Captain Benjamin Horningold recognized the unique abilities of his the young Teach, and began to groom the man as his successor. Piracy was not a long-term career. Most pirates were either arrested or killed, or they retired after a short period of time. The risks were substantial, but profits made during three years of plundering could be enough to set a man up for the rest of his life.

Horningold and Blackbeard captured a two-hundred-ton French slave ship, Concorde. It was a substantial windfall. Horningold accepted the king's pardon for his crimes and retired from piracy to a quiet life. As a parting gift he presented his young prot‚g‚ the slave ship, which Blackbeard renamed Queen Anne's Revenge.

Blackbeard was a man of imposing stature. He stood over six feet two inches and weighed about two hundred and fifty pounds. This was during an era where, due to poor diet in childhood, men rarely grew past five feet six inches and one hundred pounds. Blackbeard towered above most men. His signature feature was a coarse, thick wild black mane of facial hair, which he festooned with colorful ribbons. When charging into battle, he weaved lit fuses into his beard so that his face was encircled with a ring of smoke, illuminated by the red glow of hissing fuses. Armed with swords and a trio brace of pistols slung from bandoleers, he looked like a demon from hell-which was his goal. Blackbeard was a master of what we now call "psychological warfare." He knew if he could frighten his opponents they would be less apt to fight a protracted battle.

His normal drink was rum laced with gunpowder. He would light the concoction and drink it down in one gulp, leaving a flame in the glass, his beard singed and smoldering. He delighted in taking two or three crewmen with him into the hold, closing the hatches and lighting several pots of brimstone. He and his crew would sit in the darkness, breathing the stench from the suffocating fumes until one by one the crewmen begged for release. Blackbeard would be the last man to climb from the hold, laughing at their weakness.

Periodically, Blackbeard would kill one of his crew for some minor offense. He claimed that if he "didn't kill one of my men now and then, they would forget who was in charge."

Blackbeard had one weakness though-women. Most pirates used prostitutes while in port, but not Blackbeard. He typically married the girls he wanted. He loved females, but had no intention of committing himself to one woman. While in port, he would pick out a woman in a tavern and bring her on board. He would have another pirate captain perform a wedding ceremony and for the next several weeks, he enjoyed the life as a married man. However, Blackbeard's idea of marriage was quite unusual.

After the "wedding" night it was his custom to force his "wife" to prostitute herself, sometimes at the point of a sword. He would allow the members of his crew, which often numbered over three hundred, to pay for the pleasure of sleeping with the captain's "wife." When he left port, he would leave his "wife" behind. Blackbeard left more than fourteen "wives" scattered throughout Caribbean and south Atlantic coastal cities.

During an eighteen month period (1717-1718), Blackbeard terrorized the coast from Honduras to Virginia, taking at least twenty prizes, more than one ship per month-an amazing record of plunder. He burned most of the ships he boarded, but added several to his growing fleet.

Most of the American colonies had turned their back on pirates by this time, except North Carolina, which was struggling for economic stability. Blackbeard had an arrangement with the governor of North Carolina, Charles Eden. In exchange for a share of Blackbeard's booty the governor would issue a pardon. Blackbeard and dozens of other pirates found a willing marketplace for their booty in North Carolina.

He also discovered a perfect hideout off Ocracoke Island, a place he called Teach's Hole. The Hole was in the midst of the Outer Banks, a bewildering labyrinth of inlets, creeks and islands, which served as a perfect location for pirates to hide from authorities, bury their treasure and refit their ships in complete privacy.

In the early spring of 1718, Stede Bonnet had been conducting business in Charles Town, secretly selling booty to some local merchants who were happy to buy the stolen goods for a fraction of their value. Bonnet was lying off the Charles Town coast planning his next move when Blackbeard's fleet sailed past. Blackbeard came aboard the Revenge and met its dandy captain.

An odder couple would be hard to imagine: Blackbeard, brutish and flamboyant with flaming beard and wild hair; and Stede Bonnet, a pudgy little gentleman-dandy wearing snow-white breeches and a powdered wig.

Blackbeard quickly realized that Bonnet's crew was unhappy with their captain. He convinced Bonnet that since the gentleman was inexperienced, and not used to the rigors of pirate command, it would be more productive if they threw in together. Blackbeard offered to put one of his men on board so that Bonnet could live a more relaxed lifestyle on his vessel.

Weeks later in May 1718, Blackbeard's six-ship pirate fleet blockaded Charles Town harbor, with Bonnet on board the Revenge as "captain-of-leisure." The pirates pillaged nine vessels and held several prominent citizens hostage, including Samuel Wragg, a member of the Governor's Council. With these hostages at his mercy, Blackbeard effectively held the city of Charles Town in his control for several days. The pirates freely roamed the city's taverns and brothels, ransacking businesses, sampling merchandise and women, and attacking anyone who put up resistance. As long as the hostages remained in Blackbeard's control the populace was powerless to retaliate. Finally in exchange for rations, gold and medical supplies, South Carolina Governor Robert Johnson was able to buy the release of the hostages. Blackbeard sailed unmolested out of the harbor with more than œ1500 of gold and silver and made a beeline for Teach's Hole.

Blackbeard advised Bonnet that to make it more difficult for South Carolina authorities to chase them down, it would be better for the pirate fleet to separate. He suggested they lie low for several weeks and explore the possibility of obtaining pardons from the North Carolina governor. Bonnet and ten of his men went ashore to obtain provisions and inquire about the pardons. As soon as they were gone, Blackbeard transferred everything of value onto his vessels, scuttled the Revenge, and left the rest of Bonnet's crew stranded on a sand bar. Bonnet returned a week later and discovered what had happened. He rescued his men and set to work repairing the Revenge, which he renamed Royal James.

After the Blackbeard blockade, Governor Johnson of South Carolina asked Colonel William Rhett to hunt down and capture the pirates terrorizing the Carolina coast. Rhett, a well-proven soldier, outfitted two ships, Sea Nymph and Henry, with one hundred and thirty men and armament. Governor Johnson then outfitted four more ships and over the next two weeks he personally commanded an expedition to root out other pirates south of Charles Town. Johnson's force killed twenty-six pirates and nineteen others were brought back to town for trial.

With the intention of locating and capturing Blackbeard, Rhett left Charles Town and headed north. Within a week Rhett discovered Bonnet refitting the Royal James in the Cape Fear River. Bonnet hurriedly tried to sail downriver to the open sea, but the Henry intervened and was able to maneuver the Royal James onto a shoal. In the process, both the Henry and Sea Nymph ran aground as well; however, the Henry was within firing range of the Royal James and, as the tide gradually came in, the two ships fought fiercely for two hours with cannons booming and muskets blazing. Rhett's ships floated free first and they moved into position. The Charles Town men stormed the Royal James and overpowered Bonnet and his crew of thirty-five.

The pirates were returned to Charles Town and imprisoned in the bastion guardhouse (in the Provost Dungeon beneath the Old Exchange Building). Bonnet was almost immediately greeted by a group of prominent gentlemen, those same scoundrels who had profited from their secret dealings with the pirate. They feared that if the pirate appeared before a judge the facts of their business relationship would be revealed. Public reaction would be strong against them. Bonnet's friends arranged to have the "gentleman" pirate placed under house arrest, and along with his lieutenant, David Herriot, the dandy was quartered at the mansion of the town marshal.

The sentries guarding the house were bribed and in the middle of the night, Bonnet and Herriot escaped, with Bonnet disguised as a woman. They used a small boat supplied by a sympathizer to escape to Sullivan's Island. The next morning their absence was discovered and Colonel Rhett formed a posse to re-capture Bonnet.

By the end of that first day, Rhett and a group of fifteen men located the pirate's hideout on Sullivan's Island. Herriot was killed during the skirmish and Bonnet surrendered, still wearing a dress .The "gentleman" pirate was shackled in the dungeon the night before his crew was marched to the gallows at White Point Gardens.

Bonnet was brought to trial in front of Justice Nicholas Trott's court. Bonnet pleaded his case, but was sentenced to be hanged. Bonnet sent urgent pleas to the governor to repeal the sentence. Several townspeople came forward to ask for his pardon, but Governor Johnson was unmoved by their pleas.

On December 10, 1718, Stede Bonnet was hanged at White Point Gardens, weeping on the gallows. His body dangled for several days before it was dumped into the low tide mud. Today, a marker at White Point Gardens memorializes the event and the location of the executions.

He never disclosed the real reason he became a pirate.

After deserting Bonnet's crew Blackbeard headed for Teach's Hole. He stayed in hiding for several weeks waiting for the outrage of his Charles Town blockade to blow over, but by the fall of 1718, he was ready for action.

He left Bath, North Carolina and almost immediately encountered two Virginia-bound, French merchant ships laden with sugar and cocoa. Blackbeard seized the ships and transferred all the cargo onto one ship. He put the French crew on the other vessel and sent them back home. He then escorted the first French ship back to North Carolina and told the authorities an amazing tale. He claimed he had discovered the ship floating in the water, deserted by the crew. Realizing the value of the cargo, Governor Charles Eden and Customs Collector Tobias Knight chose to believe the story and the three split the booty.

To celebrate his grand fortune, Blackbeard headed to Ocracoke Island. The Queen Anne's Revenge was laden with food, rum and women picked up from the waterfront. Other notorious pirates, like Calico Jack Rackham and Charles Vane, arrived at Ocracoke with more women and rum. It soon became a huge, continual party that has become known as the "Ocracoke Orgy." Hundreds of pirates spent several weeks on the island drinking, eating and whoring with more than fifty wenches.

Word began to spread among the Outer Banks citizens about the presence of so many pirates. A panic spread along the Atlantic seaboard that Ocracoke Island was going to replace the Bahamas as the new pirate headquarters.

When Virginia governor Alexander Spotswood was informed of Blackbeard's Charles Town blockade and the taking of the Virginia-bound French ships, he declared that he would not honor any pardon given to Blackbeard. Spotswood's political career was on the slide, and he believed that if he could get rid of the infamous Blackbeard, he would be a hero. Spotswood obtained two sloops (the Jane and the Ranger) and convinced the Royal Navy to supply the manpower, under the command of the oldest lieutenant in the Royal Navy, Lt. Robert Maynard. Maynard was promised a reward of one hundred pounds to bring back Blackbeard-dead or alive. Capturing Blackbeard would be a feather in his cap, and a route to a much-needed promotion. The biggest obstacle he faced was how to pinpoint the location of Teach's Hole. The problem was solved due to a lucky break-the arrest of Blackbeard's former quartermaster. Under torture, Maynard discovered the location of Teach's Hole.

Blackbeard enjoyed the orgy on Ocracoke so much that after it was over, he decided to extend the pleasure for his crew. Oblivious to the political winds blowing against him, and the executions of Bonnet and crew in Charles Town, Blackbeard left Ocracoke and headed to Teach's Hole with rum and women on board.

About the same time, Maynard set out from Virginia with fifty-eight men on two ships. They arrived at the inlet at dusk and spent a long night preparing for battle, waiting for dawn to navigate the inlet safely. Blackbeard and his men spent the night drinking and partying. In fact, most of the pirates were still drunk when the sails of Maynard's vessels became visible on the morning of November 21, 1718.

Maynard approached the Hole but, unfamiliar with the treacherous water, his two sloops ran aground on a sandbar. The pirate crew scrambled from their drinks and their women and hastily prepared for battle. While Maynard was stranded on the sandbar, Blackbeard took the opportunity to launch a full-scale assault. The half hour battle resulted in ten dead pirates, and nine wounded. Maynard lost ten men and twenty-four were injured.

The highlight of the battle was a ten-minute duel between Blackbeard and Maynard. Blackbeard suffered five pistol wounds and twenty sword slashes before he collapsed on deck. The pirate was beheaded while he was still alive. Maynard returned to Virginia with the pirate's head dangling from the mast. Blackbeard's body was stripped of flesh and hung from a pole at the mouth of the Hampton River.

The death of Blackbeard marked the beginning of the end of the golden age of piracy along the Atlantic seaboard.

Meet the Author

Mark R. Jones is a ninth-generation native of South Carolina. He is a licensed City of Charleston tour guide, conducting carriage tours for Palmetto Carriage and daytime history and nighttime ghost tours for Bulldog Walking Tours. Mark is also one of a select group of guides who conducts the Dark Side of Charleston Tour for Bulldog: the tour that inspired the writing of the Wicked Charleston books. The Dark Side is the only non-ghost nighttime tour in Charleston. On average, Mark conducts twenty tours a week, about one thousand per year. He is the author of Wicked Charleston: The Dark Side of the Holy City, which covers the history of the founding of Charles Towne from a unique perspective: drinking, prostitution and murder. The Charleston Post and Courier called the book a solid (if tipsy) foundation for the revelry to come."? Wicked Charleston, Volume 2 is the continuation of that revelry. In his free time, Mark is always on the prowl for new salacious stories about Charleston. Information about Mark, his books, tours, personal blog and speaking engagements can be found at his web site: www.wickedcharleston.net."

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Wicked Charleston: The Dark Side of the Holy City 3 out of 5 based on 0 ratings. 2 reviews.
Anonymous More than 1 year ago
Still reading it , but i liked all his other books so i dont think I will be disappointed . Like what I read so far.
Anonymous More than 1 year ago
There is very little historical fact in this text. Especially dealing with the pirate tales and descriptions. Everything about Blackbeard and Stede Bonnet are completely fiction. This author is attempting to pass off tall tales as historical fact. What a joke...