Black Flags and Jolly Rogers: 8 Icons of the Caribbean’s Golden Age of Piracy

The Caribbean Sea was a hotbed of infamous pirates during the Golden Age of Piracy in the late 17th and early 18th centuries. Many of them have since become famous in books, movies, and popular culture. In this article, we will look at eight of the most well-known Caribbean pirates from the Golden Age of Piracy.

Henry Morgan

Henry Morgan was born in Wales around 1635 and is one of the most famous pirates in history. Morgan did not necessarily see himself as a pirate, but rather as a privateer or buccaneer in the service of the English crown. Young Morgan left home to go to sea in search of money and adventure. He started as a privateer in the Anglo-Spanish War, which essentially gave him a free pass to attack and plunder enemy ships and towns.

Stories of his adventures are legendary and often elaborate to the point of fiction. He successfully and brazenly attacked Portobelo in 1668, a rich and fortified Spanish settlement. Morgan and his men used trickery and daring to take the fort, loot it, and hold it for ransom. He did not win many of his battles by force but by wits and bravado. In one story, he had friars and nuns help carry ladders up to the front of his attack to trick the Spanish defenders into not shooting at them. He is famous for his attacks on settlements in search of treasure and for becoming a kind of hero in the eyes of the English.

His theatre of choice was the Caribbean Sea, which was packed with islands and Spanish settlements. His success far surpassed that of his peers in these raids. The most famous was his raid on Panama City in 1671. The attack was a bit of a disaster, as the city was burned, but the haul of treasure was still impressive. The raid would lead to his downfall when it was discovered that he had broken a peace treaty between England and Spain.

Morgan was arrested and sent back to England, but rather than being punished for his crimes, he was knighted by King Charles II and returned to Jamaica, this time as its Lieutenant Governor. The swashbuckling pirate became a respected colonial governor and official. Morgan lived the remainder of his life in Jamaica and died there in 1688.

Captain Henry Morgan’s significance lies in his legendary story and its cultural aspects. Many novels and movies have been created over the years about pirates with nods to Captain Morgan and his life. The difference between pirates and legitimate sailors in this era was sometimes only in where you flew your flag. The “Captain Morgan” brand is among the most recognizable rums worldwide. The legendary buccaneer’s name continues to adorn products, and his influence on pirate lore is significant.

Stede Bonnet: The Gentleman Pirate of the Caribbean

Captain Stede Bonnet was a true anomaly among pirates. In 1688, Bonnet was born in Barbados to a very wealthy English family. He married and owned his own estate, and he held the rank of major in the military. However, he had run into personal problems and other misfortunes. He was having problems with his wife, and for no apparent reason, he decided to become a pirate. This is more than unusual, especially for a man with no experience at sea. Instead of hiring crew members, he bought a sloop with his own money, which he named “Revenge”, and he paid his sailors. An unusual move, as captains of pirate ships rarely paid their crews a wage.

Bonnet’s life as a pirate was full of strange events. He started by raiding merchant ships off the coast of Virginia and the Carolinas, taking over ships and burning them. However, his inexperience at sea showed, and he became the subject of some strange adventures. On one such occasion, Bonnet’s ship was badly damaged in a storm because he was unsure how to steer through it. On another, Bonnet was said to read books aloud to his crew, a pastime not normally associated with pirates.

Bonnet would operate mostly off the Eastern Seaboard of America, ranging from New York to the Carolinas. Bonnet’s successes were an amalgam of victory and fumble. The “Protestant Caesar” was one of Bonnet’s great captures, a merchant ship carrying precious cargo. Bonnet’s inexperience with the sea led to an unorthodox partnership with the more experienced and better-known Blackbeard (Edward Teach). The two pirates would have a run of small raids together until Blackbeard betrayed Bonnet, stealing his ship and leaving him on an island to die.

Bonnet was captured in 1718 by Colonel William Rhett off the Cape Fear River and put on trial in Charleston, South Carolina, for piracy. Stede Bonnet was hanged in 1718, which marked the end of his life and piracy. Bonnet’s piratical career is still discussed today for the transition from a life of leisure to his pirating days and his miserable end.

Bonnet is a significant cultural icon for many reasons, including that his piracy may not have been a result of his desire for money or advancement, but rather to get away from his personal troubles and leave his life behind. This is a unique case of piracy that has fascinated historians and other writers for years.

Although he is not as well-known as some other pirates in the public mind, such as Blackbeard or Calico Jack, Stede Bonnet is well-known within the pirate history community and has had his story told in multiple books and documentaries, as well as on pirate-related merchandise. Bonnet proves that even in the “Golden Age of Piracy” there was never a shortage of eccentric or atypical pirates.

Calico Jack: The Flamboyant Pirate of the Caribbean

Jack Rackham was born sometime around 1682. His life prior to 1718 is not well documented. It is known that he had joined a pirate ship as a quartermaster for the infamous pirate Charles Vane at the beginning of the 18th century. When Vane showed weakness during an attack by a French warship, Rackham led a mutiny against the captain and took over the ship. From that point forward, Calico Jack was to be known as a full-fledged pirate captain.

Under Rackham, they hoisted a new Jolly Roger, a skull with crossed swords underneath, a symbol that would come to represent the later Golden Age of Piracy. Calico Jack was a bold pirate, and most of his attacks were on smaller ships in the inlets and along the shores of Jamaica and the Bahamas. It was here that he met Anne Bonny, a fiery young woman and the daughter of a plantation owner. They were soon fated to cross paths again, and she, under the guise of a man, was soon one of his crew, later joined by Mary Read, another female pirate.

Rackham operated in the Caribbean, particularly around the Bahamas, Cuba, and Florida. He did not acquire as much treasure as some of his contemporaries, but his audacity, flamboyant style, and partnership with two of the most famous female pirates of all time have given him a special notoriety. Rackham’s propensity for flamboyant, even reckless, behaviour was also his undoing. Rather than, as was common among pirates, attacking under cover of darkness, he frequently took ships in broad daylight, often running afoul of heavily armed merchantmen.

Rackham’s pirating career was as brief as it was eventful. In 1720, pirate hunter Captain Jonathan Barnet captured Rackham and his crew while they were drunk. Rackham was tried and sentenced to death by hanging. Legend has it that Anne Bonny visited Rackham in his cell before his execution in Port Royal, Jamaica. Bonny did not weep with him, as he expected, but told him he should have fought harder, allegedly saying, “Had you fought like a man, you need not have been hanged like a dog.”

Calico Jack’s appearance in popular culture is extensive. His flag, the skull with crossed swords, is one of the most well-known pirate symbols today. His exploits have inspired and been fictionalized in many books, films, and TV series. Calico Jack is a major character in TV series like Black Sails and video games such as Assassin’s Creed IV: Black Flag. His piracy and reputation make him a subject of fiction and non-fiction works published hundreds of years after his death.

Anne Bonny: The Fiery Female Pirate of the Caribbean

Anne Bonny was born in Ireland around 1700, and her childhood was to be marked by controversy from the start. Her parents were lawyer William Cormac and his housemaid, making Anne an illegitimate child. Her father’s affair and Anne’s birth scandalized the family, and they were forced to move to the New World. Settling in Charleston, South Carolina, Anne’s reputation for a fiery temper came early; legend says she stabbed a servant girl with a knife in her early teens. It only got worse with time.

Anne was a young woman when she married a small-time pirate, James Bonny. Her father disapproved of her relationship with Bonny, and Anne was disowned. The couple left for Nassau in the Bahamas, an infamous pirate haven. Anne soon met the pirate John “Calico Jack” Rackham. The two fell in love and shared a lust for the sea and crime. Anne joined Rackham’s crew. Anne disguised herself as a man to avoid detection and bias against women.

Bonny and her fellow female pirate, Mary Read, went on several pirating adventures in the Caribbean, with a fearsome reputation for bloodthirstiness and fighting prowess. One of the most popular legends concerning Bonny and Read is their fight against a British naval ship that came to capture them. While most of Rackham’s men hid below deck, Anne and Mary fought off their assailants, guns blazing and swords clashing.

Anne and Calico Jack sailed mostly around Jamaica and Cuba. She was a successful pirate, despite the many obstacles a woman would have faced in a pirate crew. Anne, Rackham, and their crew captured several ships and accumulated treasure and notoriety.

In 1720, their ship was attacked by a British warship. Calico Jack and most of his crew were taken prisoner and later executed. Anne and Mary Read were sentenced to death, but their executions were delayed due to pregnancy. Mary Read died in prison a few months later from fever, but no record of her companion’s execution exists. It is likely that Anne escaped or was released, possibly by her father, and lived the remainder of her life in obscurity.

Anne Bonny has had a lasting impact on popular culture as one of the few known female pirates of the “Golden Age of Piracy.” Her life and legend have been the subjects of books, films, and television shows, and she has been depicted in various forms of media over the years. Her story of adventure, romance, and rebellion has resonated with audiences and inspired writers and artists to explore her life and times. From the video game “Assassin’s Creed IV: Black Flag” to the television series “Black Sails,” Anne Bonny’s legacy as a pirate continues to captivate and inspire.

Mary Read: The Fierce Female Pirate of the Caribbean

Mary Read was an English pirate who had an interesting early life story. Mary’s mother disguised her as a boy in order for her family to continue receiving the financial support that her grandfather was providing for her late son. Mary accepted this lie and the disguise. This was the early stages of what was to be her life of adventure in the typically male world.

While passing as a man, Read continued to serve in the British military and showed great promise in battle during the War of the Spanish Succession. It was during this war that she fell in love with a Flemish soldier. After revealing her secret to him, they married and ran an inn in the Netherlands. When her husband died, a grieving Mary, back in male clothing, returned to the sea.

It did not take long before Mary’s ship was taken by pirates. At first, she was forced to be one, but she soon grew to love the freedom. Mary was a wild and strong person, which made piracy on the high seas a natural fit. She was soon sailing with another famous pirate captain, Calico Jack Rackham, along with his female companion, Anne Bonny. The three of them were quite a trio of pirates in the Caribbean. Many legends exist about their adventures. One is that, even dressed as a man like she often was, Mary could not resist taunting an enemy by letting him know she was a woman before she out-fought him in a duel.

Mary Read’s career as a pirate, however, was brief. Rackham’s ship was captured while it was anchored off the coast of Jamaica in 1720. Most of the drunken crew was taken with little resistance. Mary and Anne were supposedly valiant in their struggle against their captors. The female duo, along with the rest of Rackham’s crew, was sentenced to death by hanging. The women’s executions were delayed; however, both Mary and Anne claimed to be pregnant. Mary supposedly died in prison of fever or possibly complications from childbirth.

Mary Read’s story has lived on for centuries. As one of history’s rare female pirates, Mary Read has become a symbol of women’s resistance to patriarchal authority. The details of her life, closely linked with Anne Bonny’s, have been told many times over in novels, films, and television series, as well as celebrated for their boldness and spirit. More recently, she has been added to a video game world and appears in Assassin’s Creed IV: Black Flag.

Captain Kidd: The Pirate Who May Have Been Wrongly Condemned

William Kidd was born into a poor family in Scotland around 1645. Little is known of his childhood. There are conflicting stories as to whether he was born in Greenock or Dundee. By the late 1680s, Kidd had become a seaman, and by 1689, he was part of a French-English pirate crew, pillaging in the Caribbean.

Kidd became a pirate in an unusual way. Sent out by the British crown to hunt pirates, he rapidly changed from pirate-killer to pirate. Kidd had been given a privateer’s license by the English government to capture enemy French ships and attack pirates. In this capacity, he was given the “legal” right to plunder and pillage, on the condition that he share some of his loot with the English crown. In the open waters, it was often difficult to know who was a legal target and who was not. This grey area, along with the possibility of raking in a great deal of wealth, led Kidd to piracy.

Kidd’s most infamous crime was the seizure of the Armenian ship “Quedagh Merchant” and its cargo of valuable silks, gold, silver, and spices. While the ship was under French pass (and therefore a legitimate prize for an English privateer), its master was an Englishman. The seizure of the Quedagh Merchant created a scandal in British and colonial society and is considered the turning point in Kidd’s image, from that of a privateer to a pirate.

His piracies were spread over a huge area, from the Caribbean to the Indian Ocean. However, the extent of his success as a pirate is questionable. Although Kidd did amass some treasure, his failure to distinguish between legal and illegal targets and his alleged cruelty towards his crew and prisoners left him with many enemies.

Captain Kidd did not have the happy ending to his career, as he neither died heroically in battle nor did he ever have the pleasure of returning home to a life of riches. After returning to New York in a failed attempt to clear his name, he was arrested and sent to England for trial. Despite his efforts to show that his conduct had been in accordance with his commission, he was convicted of piracy and the murder of one of his crewmen. In 1701, William Kidd was hanged at Execution Dock in London. His body was then gibbeted over the River Thames as a warning to others.

The legacy of Captain Kidd is larger than life in terms of cultural impact. Rumors of Kidd’s buried treasure have circulated for generations, and over the years, countless treasure hunters have sought his legendary cache, especially on the East Coast of the US and the Caribbean. The numerous questions surrounding his true character and motives have inspired a wide variety of books, movies and songs.

He has been depicted in popular media as either a cutthroat pirate or as the victim of a political conspiracy. Characters and events from Kidd’s life have been incorporated into movies such as Pirates of the Caribbean and video games such as Assassin’s Creed, among others. The mystery of Captain Kidd continues in popular culture to this day.

Bartholomew Roberts: The Prolific Pirate Known as Black Bart

One of the largest and most feared pirates of the Golden Age of Piracy was Bartholomew Roberts, better known as Black Bart. Roberts was born in Pembrokeshire, Wales, in 1682. There is very little information available on his early life. He joined the sea as a young man, but it was not until 1719 that he was forced into piracy.

He was the third mate aboard a ship that was captured. He was taken and made to join the pirate crew. He quickly adapted to his new lifestyle and was elected captain after their previous captain died.

Roberts is said to have been a teetotaler and a great lover of music. It is well documented that he would capture musicians from ships he captured and make them his own crew. Despite his taste in culture, he was also known to be brash. He captured the governor of Newfoundland, looted the harbor, and burned and pillaged the town of Trepassy.

Operational mostly in the Americas and West Africa, Roberts enjoyed an amount of success that only a few in piracy ever would. During his lifetime, he captured more than 400 ships in his piratical exploits. As captain of several vessels during his career, Black Bart used many. His most famous ship was the “Royal Fortune”, which was fitted with cannons and an expert crew to intimidate his targets.

His death was nearly as theatrical as his life. In February 1722, the pirate was at anchor off the Point of Cape Lopez, in modern-day Gabon, when a British man-of-war, HMS Swallow, attacked his vessel. During the battle, Roberts was hit in the throat by grapeshot and killed. His crew, being ever so loyal, wrapped him in a sail and buried him at sea as he wished.

In terms of cultural impact, Bartholomew Roberts’ contribution to the popular image of the pirate is remarkable. His code of pirate conduct established the guidelines and rules of what behavior pirates were expected to follow. The articles dictated standards of decency, or “etiquette” as it were, for pirates, stating, among other things, that there was to be no gambling on board and that all lights were to be extinguished by eight. The code, or at least one very similar to it, has been an allusion and/or used as a plot device in many pirate stories since.

His flashy taste, fondness for finery, and the scarlet and gold of his ship’s ensign have contributed to the portrayal of pirates in literature and film.

Black Bart’s image is alive and well in pop culture, from films and books to even video games. Black Bart has been depicted in everything from the well-known novels of Defoe to recent movies and video games such as “Assassin’s Creed”. He will always be known as the very definition of a pirate captain: a cutthroat, a dandy, and the most successful pirate of all time.

Blackbeard: The Fearsome Legend of Edward Teach

Born Edward Teach or Thatch, Blackbeard has since become one of the most famous pirates in history. Little is known of his early life, as few records of his birth or upbringing exist. Some historians think he was born in Bristol, England, around 1680, while others have suggested that Teach may have been born in Jamaica. By the early 1700s, however, Teach had begun his legendary career as a pirate.

Appearance: Tall and powerfully built, Blackbeard had a long, thick, coal-black beard that curled below his chin. Legends say that during combat, he often took slow-burning fuses and tucked them into his beard, lighting the fuses to make it appear as if his head were ablaze with many fires. By this, he would look completely demonic to his enemies.

Blackbeard was primarily active around the West Indies and the eastern coast of the American colonies. He once blockaded the port of Charleston, South Carolina, and took the city hostage in exchange for a large ransom. Blackbeard’s most powerful ship was Queen Anne’s Revenge, armed with 40 guns and manned by a crew of over 300 pirates. Throughout his pirating career, Blackbeard captured a large number of ships, netting him an immense treasure haul.

Nonetheless, as was the case with many pirates of his time, Blackbeard’s reign of terror was short-lived. Virginia’s Governor, Alexander Spotswood, was concerned about the pirate infestation and sent Lieutenant Robert Maynard to capture or kill Blackbeard. On November 22, 1718, Blackbeard was killed in an all-out battle with Maynard’s men off the coast of Ocracoke Island, North Carolina. Legend has it that Blackbeard was shot five times and cut about twenty times before he died. His head was then cut off and hung from the bow of Maynard’s ship as a warning to other pirates.

Blackbeard’s cultural impact is vast. He is considered the archetypal pirate in popular consciousness. His untamed look, guileful strategy, and vicious governance are paradigmatic of the Golden Age of Piracy.

Blackbeard’s image and name have been used and alluded to innumerable times in popular culture. From films like Pirates of the Caribbean to books, comics, video games, and even songs, Blackbeard’s image has been used. The state of North Carolina, which Blackbeard pillaged, has museums dedicated to his life, and the “Blackbeard Pirate Festival” is held annually in Hampton, Virginia.

The Golden Age of Piracy’s Long Lasting Legacy

The late 17th to early 18th centuries, a period known as the Golden Age of Piracy, was marked by a series of events and individuals that left an indelible mark on history. This was a time when piracy was at its peak, and the high seas were ruled by notorious figures such as Blackbeard, Anne Bonny, and Captain Kidd.

These individuals became legends, living on the edge and defying authority in a world where survival was a constant struggle. Their stories of daring escapades, treasure hunts, and daring sea battles have been passed down through the ages and have inspired countless books, movies, and other forms of media.

The Golden Age of Piracy was also a time of change and progress, and its events have had a lasting impact on modern society. The rise of piracy during this period challenged traditional power structures and forced governments and privateers to adapt.

In addition, the stories of piracy during this time have shaped modern perceptions of rebellion, entrepreneurship, and the power of the sea. The romanticized image of the pirate has become ingrained in popular culture and has influenced everything from literature and film to modern-day business practices.

Despite the passing of time, the legacy of the Golden Age of Piracy continues to live on, reminding us of the power of the human spirit and the unrelenting drive to explore, conquer, and break free from the chains of conventionality.