The History of Infamous Pirate Flags and the Stories Behind Them

Pirates and their flags have long captured the imagination of people everywhere, from the skull and crossbones of childhood cartoons to the dark and terrifying realities of piracy on the high seas. But what were the stories and meanings behind these infamous pirate flags, and why did they inspire both fear and fascination? In this article, we will explore the history and symbolism of four of the most famous pirate flags, from Blackbeard’s imposing banner to the blood-red standard of Emanuel Wynn, and discover the tales of the men who flew them. So hoist the Jolly Roger and set sail with us on this journey into the world of pirates and their flags.

Blackbeard’s Flag

Blackbeard'S Flag
Blackbeard’s flag, also known as “the Jolly Roger,” is one of the most recognizable pirate flags in history. The flag features a horned skeleton holding an hourglass and a spear pointing to a red heart, with drops of blood surrounding it. The symbolism behind the flag is intimidating, as it represents death and the inevitability of time running out. It was meant to strike fear and surrender into the hearts of their enemies. Blackbeard, whose real name was Edward Teach, was a notorious pirate who sailed the seas during the Golden Age of Piracy. He was known for his ruthless tactics and barbaric behavior, which added to the fear struck into the hearts of those who saw his flag. To read more about the history of infamous pirate flags, check out the evolution of pirate flags.

The Symbolism Behind the Flag

The Jolly Roger flag of Blackbeard, with its skull and crossed swords design, represents a chilling symbol of piracy. However, this infamous flag has more to it than meets the eye. The skull symbolizes death and the crossed swords hint at the deadly force that lies ahead for anyone who opposes the pirate ship. Historians believe the horned skeleton beneath the skull might be a reference to the devil, signifying that pirates were no less than Satan’s army. Interestingly, the design of the flag that we associate with pirates today might never have existed. There is little evidence that pirates actually flew the Jolly Roger as we commonly know it today. In fact, the famous black flag with the skull and bones was only flown by a few pirate ships. However, this flag served as inspiration for countless other pirate flags, some of which are still famous among pop culture enthusiasts. The symbolism behind pirate flags is intriguing, and for those that are interested in learning more, there are plenty of resources available on the symbolism of pirate flags and how they were used for communication among pirates.

Blackbeard’s Notorious History

Blackbeard, whose real name was Edward Teach, was one of the most famous and feared pirates during the Golden Age of Piracy. He operated in the Caribbean and along the coast of North America in the early 18th century, and his reputation for violence and terror was well known.

Blackbeard’s fleet consisted of several ships, including a former French slave ship which he renamed the Queen Anne’s Revenge. He was known for his intimidating appearance, often braiding his long black beard and lighting it on fire during battles to strike fear into his enemies.

One of Blackbeard’s most notorious acts was the blockade of Charleston, South Carolina in May 1718. He and his crew captured several ships coming in and out of the harbor, holding them for ransom and causing panic in the town.

However, Blackbeard’s reign of terror came to an end in November 1718, when he was ambushed and killed by a Royal Navy force led by Lieutenant Robert Maynard. His head was mounted on the bowsprit of Maynard’s ship as a warning to other pirates.

Despite his short career, Blackbeard’s legend lives on, cemented in part by the infamous flag he flew, which depicted a devil holding a spear over a heart. Want to learn more about other famous pirate captains’ flags? Check out our article on Famous Pirate Captains’ Flags.

Calico Jack’s Jolly Roger

Calico Jack’s Jolly Roger, also known as the “Jolly Roger with two Calico Jacks,” is one of the most recognizable pirate flags in history. The flag featured a skull with crossed swords and two hearts, one with a drop of blood, all against a black background. The crossed swords are likely a nod to Calico Jack’s reputation as a skilled swordsman, while the two hearts may symbolize his love for two female pirates in his crew. Unfortunately for Calico Jack, his time as a pirate was short-lived, as he was captured and executed in 1720. Nevertheless, his flag lives on as a symbol of the Golden Age of Piracy. The flag’s design has also influenced pop culture, appearing in movies, video games, and even on merchandise. While the flag’s original meaning has been lost to time, its significance as a symbol of piracy will endure for years to come.

Design and Meaning

Design and Meaning of Calico Jack’s Jolly Roger

Calico Jack’s Jolly Roger is one of the most recognizable pirate flags of all time. Its design features a skull wearing a red bandana with two crossed swords underneath.

The skull and crossed bones symbolize death, danger, and a willingness to fight to the death. Meanwhile, the red bandana was a symbol of resistance against authority.

Interestingly, the design of the Jolly Roger evolved over time. Early pirate flags simply featured a skull and crossbones, while later versions incorporated other symbols like hourglasses, skeletons, and hearts.

The Jolly Roger was a fairly common design among pirate flags, but Calico Jack’s version was unique in its use of the red bandana and crossed swords.

Meaning in the Pop Culture

The Jolly Roger has become an iconic symbol and is often used in pop culture to represent pirates. It has appeared in countless movies, TV shows, and books. It is also the subject of many toy and costume designs.

Interestingly, the Jolly Roger has even made its way into the world of sports. The Carolina Panthers, an American football team, use a variation of the Jolly Roger as their team logo.

Note: If you want to learn more about the significance of pirate flags, read our article on The Significance of Pirate Flags. If you want to know what happened to pirate flags after the end of the Golden Age of Piracy, check out our article on The Fate of Pirate Flags.

The Tragic Story of Calico Jack and His Crew

The story of Calico Jack and his crew is one of the most tragic and notorious in pirate history. Jack Rackham, also known as Calico Jack, was a famous pirate who sailed in the Caribbean during the early 18th century. His Jolly Roger flag featuring a skull with crossed swords became iconic in pirate lore. However, while his flag gained popularity, the same could not be said for his crew.

In October 1720, Rackham and his crew were captured by bounty hunter Jonathan Barnet, who pursued them after they stole a ship belonging to his employer. Rackham’s crew consisted of several women, including Anne Bonny and Mary Read, who dressed as men to join the pirate crew. The women were known for their bravery and skills in combat, making them valuable members of the crew.

Unfortunately, their capture marked the end of their brief but notorious career. While the male members of the crew were tried and hanged, Bonny and Read managed to extend their lives by revealing their pregnancies. However, Mary Read died in prison from a fever, and Anne Bonny’s fate remains unknown.

The tragic end of Calico Jack and his crew serves as a reminder of the harsh realities of piracy during that era. Instead of the romanticized depictions that appear in pop culture and media, piracy was often bloody, violent, and short-lived. The story of Calico Jack and his crew has found its way into various forms of pop culture and media, demonstrating the continued fascination and captivating appeal of piracy.

Henry Avery’s Red Jack

Henry Avery'S Red Jack
Henry Avery, one of the most successful pirates in history, flew a flag known as the Red Jack. The flag featured a skull with an hourglass in one hand and a spear in the other, with a bleeding heart below. This flag was particularly menacing, as the hourglass was a symbol of time running out, while the heart represented the fate of those who crossed the pirate. The origins and significance of the flag have been the subject of debate, with some historians believing that it may have been designed by Avery himself, while others suggest that it was a variant of the more common Jolly Roger. Regardless of its origins, the Red Jack became infamous thanks to Avery’s successful exploits, which included capturing one of the most valuable ships of the time, the Ganj-i-Sawai. Today, the Red Jack is still recognized as one of the most recognizable pirate flags in history and continues to be featured in popular culture.

Origins and Significance

The flag of Henry Avery, known as the Red Jack, is one of the most infamous pirate flags in history. Its origins and significance hold an important place in the annals of piracy. The flag features a skull with crossed bones, surmounted by an hourglass and above them, a bleeding heart. The symbolism of the flag is steeped in the notions of mortality and the fleeting nature of life.

The hourglass on Avery’s flag is a significant symbol. It symbolizes the inevitable end of life and the limited time each person has on earth. The skull and crossbones represent death and the transience of human existence. The bleeding heart, which is often depicted dripping blood onto the skull, is a symbol of the emotional and physical pain that human beings experience in life.

As a pirate, Henry Avery was a fierce and feared captain. He made his name as a pirate in the late 1690s and early 1700s, operating primarily in the Indian Ocean and along the coast of Africa. Avery’s flag was meant to strike fear in the hearts of his enemies. When the Red Jack was raised, it signalled that anyone who crossed Avery would suffer a brutal and bloody fate.

Despite his fearsome reputation, the origins of Avery’s flag are shrouded in mystery. No one knows for certain how the Red Jack came to be, although there are many theories. It is possible that Avery himself designed the flag, incorporating elements that held personal significance for him. Alternatively, the flag may have been designed by one of Avery’s crew members, inspired by the symbolism of death and mortality.

What is certain is that the Red Jack has a place in pirate lore that is both significant and enduring. For centuries, the flag has been associated with piracy and has been used as a symbol of rebellion and resistance. Today, the Red Jack is still recognized as one of the most iconic pirate flags in history, its origins and symbolism continuing to capture the imaginations of people around the world.

The Legend of Henry Avery

According to legend, Henry Avery was born in the mid-1600s in England and became a sailor at a young age. He served in the Royal Navy before turning pirate, and quickly made a name for himself as a skilled navigator and leader.

One of Henry Avery’s most famous exploits was the capture of the Ganj-i-Sawai, a large Indian treasure ship, in 1695. The ship was said to be carrying a vast fortune in gold, silver, and jewels, and Avery and his crew of pirates made off with the loot.

This daring raid made Avery one of the wealthiest pirates of his time, and he subsequently disappeared from history. Some legends suggest that he retired to a life of luxury, while others claim that he was captured and executed by the British navy.

Despite the mystery surrounding his fate, Henry Avery’s legend as a daring and successful pirate persists to this day. His reputation as a skilled navigator and leader continues to inspire admiration and awe amongst those fascinated by pirate history.

The Blood Flag

The Blood Flag was a feared and gruesome pirate flag that served as a warning to potential targets. Its red background symbolized the bloodlust of its captain and crew. The flag featured a skull wearing a bandana and brandishing a dagger in its teeth, with an hourglass beside it symbolizing the limited time their prey had left. The flag belonged to the pirate Emanuel Wynn, who was notorious for his brutal methods of taking over ships and crews. Wynn and his crew were known to show no mercy to their victims, often leaving no survivors. The Blood Flag effectively communicated their ruthlessness, striking fear into their enemies. Wynn eventually met his end in a battle with the British navy, but his legacy, and that of his infamous flag, lives on in pirate lore.

Meaning and History

The Blood Flag, also known as the Red Flag, is a notorious pirate flag that has a dark and bloody history. This flag was used by Emanuel Wynn, a cruel and ruthless pirate, who terrorized the Caribbean seas during the early 18th century. The flag features a black background with a bright red design of a man holding a sword in one hand and a bleeding heart in the other.

The meaning behind the Blood Flag is quite clear and obvious – it represents the pirates’ willingness to fight to the death and their utter disregard for human life. The image of the man holding a sword and a bleeding heart is a symbol of their bloody and violent nature, showing their enemies what they can expect if they choose to stand in their way.

The history of the Blood Flag is just as brutal as its symbolism. Emanuel Wynn was a notorious pirate who was known for his cruelty and ruthlessness. He was one of the most feared pirates of his time, and his flag was a warning to anyone who dared to cross his path.

Wynn and his crew would often torture and kill their victims, leaving their bodies to be picked apart by the vultures and sharks. The Blood Flag would be flown as a warning to other ships that Wynn and his crew were coming, and they should flee if they valued their lives.

Despite the fact that Wynn and his crew were eventually captured and executed for their crimes, the Blood Flag remains a symbol of the brutal and violent nature of piracy. It is a chilling reminder of the atrocities that were committed on the high seas during the era of piracy, and a testament to the enduring power of symbolism.

The Brutality of Emanuel Wynn and His Crew

The Blood Flag, also known as the Jolly Roger, was the flag used by the notorious pirate Emanuel Wynn and his crew. This flag was unique in that it featured a white skull and crossbones on a deep red background that symbolized the merciless and bloodthirsty nature of Wynn and his pirates.

Wynn was infamous for his sheer brutality towards those he plundered, becoming one of the most dreaded pirates in the 18th century. He was known for targeting ships belonging to powerful navies, including the British and Spanish, and often used violent tactics to achieve his goals. Wynn’s name struck fear into the hearts of sailors everywhere, and his flag served as a warning of the cruelty that awaited anyone who dared to cross his path.

One of Wynn’s most brutal acts was the torture of a captured Dutch captain. After plundering the captain’s ship, Wynn’s crew subjected the captain to horrific levels of violence. They burned his feet with candles, cut off his ears, and finally slit his throat before tossing his body into the sea. Wynn himself reportedly participated in the torture, displaying a level of ruthlessness and inhumanity that shocked even his fellow pirates.

Wynn and his crew continued their reign of terror until they were finally captured by the Spanish in 1704. The surviving crew members were put on trial and executed, including Wynn himself who was said to have met his end with characteristic defiance, showing no remorse for his crimes.

The Blood Flag remains as a testament to the extreme violence and brutality of Wynn and his crew. Its deep red background and stark white skull and crossbones are a chilling reminder of the horrors committed by these pirates. The flag serves as a warning to all those who follow in their footsteps, that their actions will not go unpunished.


In conclusion, the stories and symbolism behind infamous pirate flags provide a fascinating glimpse into the world of piracy. Each flag had its own unique design and meaning, reflecting the values and beliefs of the pirates who flew it. Blackbeard’s Jolly Roger embodied fear and intimidation, while Calico Jack’s Jolly Roger represented freedom and rebellion. Henry Avery’s Red Jack symbolized revenge and the desire for wealth, while the Blood Flag was a gruesome reminder of the brutality and violence that characterized piracy.

Although piracy is often romanticized in popular culture, the reality was far more grim. Pirate life was one of constant danger and hardship, marked by violence, disease, and death. The stories of Blackbeard, Calico Jack, Henry Avery, and Emanuel Wynn serve as a reminder of the harsh realities of life at sea.

While the days of pirates and their flags may be long gone, their legacy lives on. The symbolism and stories behind their flags continue to captivate us to this day. As we look back on these infamous flags, we are reminded of the timeless human desire for adventure, wealth, and freedom.

Frequently Asked Questions

What are pirate flags known as?

Pirate flags are known as “Jolly Rogers”.

Why did pirates fly flags?

Pirates flew flags to strike fear into the hearts of their enemies and to signify that they were pirates.

What does the skull and crossbones symbolize on pirate flags?

The skull and crossbones on pirate flags symbolize death and danger.

Did all pirates have a Jolly Roger?

Not all pirates had a Jolly Roger, but it was a popular practice among many infamous pirates.

Were pirate flags ever used as a negotiation tool?

Yes, pirates sometimes used their flags as a negotiation tool, threatening to attack if their demands were not met.

What does the color red represent on Henry Avery’s Red Jack flag?

The color red on Henry Avery’s Red Jack flag represents blood and the pirates’ willingness to fight to the death.

Did Blackbeard really light his beard on fire?

There is no historical evidence to suggest that Blackbeard actually lit his beard on fire, but it is a popular myth associated with the infamous pirate.

What is the story behind Calico Jack’s Jolly Roger?

The design of Calico Jack’s Jolly Roger features a skull with two crossed swords underneath. It is said to represent Jack’s “scofflaw” attitude and disregard for authority.

What is the Blood Flag?

The Blood Flag was a Jolly Roger flown by Emanuel Wynn and his crew. It was said to have been stained with blood from their victims and symbolized their brutality.

Where can I see pirate flags today?

Pirate flags can be seen in museums and historical sites, including the Pirate Soul Museum in Florida and the National Maritime Museum in London.


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