The Evolution of Pirate Flags Throughout History

Pirates have captured the imagination of people for centuries. From the days of ancient seafarers to the modern-day film industry, pirates have been a source of fascination. Along with their adventurous lives, pirates are also known for their use of symbols and flags. These flags were used to intimidate enemies and to indicate their pirate status. In this article, we delve into the evolution of pirate flags throughout history, highlighting the most famous and iconic designs. Whether you are a history buff or a fan of popular culture, this article will take you on a journey through the fascinating world of pirate flags. So, grab your eye patch and hoist the mainsail as we set off on this adventure.

Early Pirate Flags

Early Pirate Flags
Early pirate flags were not as recognizable as the black-and-white Jolly Roger flag that has become synonymous with pirates today. Many different designs were used, including the Red Flag and the Black Flag, both of which invoked fear among those who saw them. These flags were often adorned with various symbols and colors to intimidate potential victims. In fact, it was not until the turn of the 18th century that the use of a consistent pirate flag became commonplace. To learn more about the symbolism and origins of pirate flags, check out our article on the subject.

The Jolly Roger

is probably the most recognizable pirate flag of all time. It was originally used by the pirate Capt. John Avery in the late 17th century. The flag has a black background with a white skull and crossbones design. The skull and crossbones symbol represents death and was intended to strike fear into the hearts of the pirates’ enemies. The white color of the skull and crossbones stands out boldly on the black background, making it easy to see from a distance.

The actual term “Jolly Roger” didn’t come into use until the early 18th century. It is believed to be derived from the French phrase “joli rouge,” which means “pretty red.” This is likely in reference to the red flags flown by French privateers or pirates. Over time, the term “jolly roger” came to refer specifically to the black pirate flag with the white skull and crossbones design.

Pirates would often modify the Jolly Roger design to fit their particular crew or captain. This was done by adding custom elements or symbols, such as an hourglass to symbolize the race against time or the devil to represent the crew’s ruthless nature. Some pirates would also customize the flag with their murder or robbery victims’ heads to further intimidate their enemies.

Today, the Jolly Roger flag remains an iconic symbol of piracy and has become a recurring visual in popular culture. However, its authenticity is often challenged as some argue that the skull and crossbones design was never widely used by pirates during the Golden Age of Piracy. Regardless of this argument, the flag continues to maintain its significance as a symbol of piracy and continues to intrigue historians and collectors alike.

The Red Flag

One of the earliest pirate flags, , was flown by Captain Emmanuel Wynn. The flag showed a black silhouette of a human arm holding a short sword, on a bright red background. This symbolized the pirates’ willingness to fight and their refusal to surrender. The red color was also considered by many to be a symbol of danger and blood, which further emphasized their ruthless reputation.

Interestingly, the red flag was also commonly used by military ships to indicate that they had declared war. This fact made it easier for pirate ships to sneak up on their targets because they could fly the same flag and not give away their intentions until it was too late. The use of the red flag exemplified the pirates’ deceptive tactics, and their willingness to do whatever it takes to get what they wanted.

While the red flag was not as well-known as the Jolly Roger or the Black Flag, it remains an important symbol of pirate history. Its legacy lives on in modern-day pirate movies and popular culture, reminding us of the ruthless and daring nature of these seafaring outlaws. The piracy industry may have been stamped out, but the red flag serves as a reminder of its once powerful existence.

If you’re interested in learning more about famous pirate flags and their stories, or the legalities of collecting pirate flags, check out our articles on famous pirate flag stories and the legalities of collecting pirate flags. You may also be curious about the value of authentic pirate flags on the collector’s market or the anatomy of pirate flag elements, both of which are covered in-depth in our articles on the value of authentic pirate flags on the collector’s market and the anatomy of pirate flag elements. Finally, if you’re interested in pirate flag design, colors, and patterns, as well as examples of prominent pirate battles and how pirate flags were displayed after a successful capture, check out our articles on pirate flag battles and pirate flag display.

The Black Flag

was one of the most famous and feared flags to sail the high seas. Its dark color and association with death and danger made it a symbol of a ruthless and unforgiving crew. Used by many pirate captains, the black flag was a signal to their victims that no mercy would be shown.

The black flag was not always solid black. Some crews added designs or symbols to make their flag unique. One example is the Jolly Roger, which featured a skull and crossbones. The Jolly Roger is believed to have originated from the French words “jolie rouge,” meaning “pretty red,” which referred to a red flag flown by French privateers.

While the black flag was used by many pirates, it was not universally adopted. Some pirates preferred to fly red flags to signal their intention to attack, while others used a variety of colors and patterns. Still, the black flag became synonymous with piracy and remains an iconic symbol of the Golden Age of Piracy.

Here are some notable pirate captains who flew the black flag:

Name Flag Design
Edward Teach Black flag with a skeleton holding an hourglass and spears, and a bleeding heart underneath.
Henry Avery Black flag with a skull and crossbones, and the letters ABH and AMH (which stood for “A Barbadian’s Head” and “A Martinican’s Head,” respectively).
Samuel Bellamy Black flag with a white hourglass and the letters AB (which stood for “A Pirate’s Life is Brief”).

Today, the black flag is still a popular symbol for pirates and is often seen in movies, books, and other media. Its association with piracy and danger continues to capture people’s imaginations.

If you want to learn more about pirate flag design, colors, and patterns, check out our article on Pirate Flag Design: Colors and Patterns.

Golden Age of Piracy Flags

During the Golden Age of Piracy, between the 1650s and 1730s, pirates developed unique and intimidating flags to strike fear in their prey and to distinguish themselves from other ships. These flags were often personalized by individual pirate captains and featured symbols such as skulls, crossbones, hourglasses, and swords. Some notable Golden Age pirate flags include Queen Anne’s Revenge Flag, which depicted a skeleton holding an hourglass, and the Blackbeard Flag, which showed a devil carrying a spear standing on two skulls. Other famous pirates, such as Calico Jack Rackham and Charles Vane, also had their own unique flags. These flags were a symbol of the pirate’s power and fearlessness, and their distinctiveness ensured that their victims knew who they were dealing with.

The Queen Anne’s Revenge Flag

The Queen Anne’s Revenge flag is an enigmatic and mysterious symbol of piracy that was flown by the infamous pirate Blackbeard. This flag is shrouded in myth and has been the subject of much speculation among historians and pirate enthusiasts alike.

Legend has it that the flag depicts a horned skeleton holding an hourglass in one hand and a spear in the other. The meaning behind this grim image is unclear, but it is thought to symbolize the fleeting nature of life and the inevitability of death.

Some historians believe that the Queen Anne’s Revenge flag was simply a variation of the Jolly Roger, with the skeleton replacing the traditional skull and crossbones. Others contend that it was an entirely new design, created specifically by Blackbeard to strike fear into the hearts of his enemies.

Regardless of its origins, the Queen Anne’s Revenge flag is undeniably a powerful symbol of piracy and has become an iconic image of the Golden Age of Piracy. Today, it is often used in pop culture to represent the romanticized notion of swashbuckling pirates and their adventurous lives on the high seas.

Although the true meaning and significance of the Queen Anne’s Revenge flag may never be fully understood, its enduring legacy as a symbol of piracy continues to capture the imaginations of people all over the world. Whether it is viewed as a terrifying emblem of death and destruction or a romantic symbol of adventure and rebellion, the Queen Anne’s Revenge flag remains an iconic representation of the Golden Age of Piracy.

The Calico Jack Flag

The Calico Jack flag is one of the most recognizable pirate flags and is closely associated with the infamous pirate John Rackham, commonly known as Calico Jack. This flag features a skull with crossed swords on a black background, with a heart in the center. Legend has it that Calico Jack designed this unique flag after being inspired by the pirate Anne Bonny, whom he was said to be romantically involved with.

Despite its notoriety, the Calico Jack flag was only flown for a short period of time. Calico Jack and his crew captured a ship in 1718 and decided to adopt its existing flag, which featured a similar skull-and-crossbones design, but with an hourglass instead of a heart. This decision ultimately cost Calico Jack his freedom, as the ship they had captured belonged to a powerful privateer who used his influence to hunt down and capture Calico Jack and his crew.

Despite this short-lived history, the Calico Jack flag has become a popular symbol of piracy and rebellion. Many modern-day pirate enthusiasts and fans of alternative media have tried to recreate the flag, sometimes with a variety of different designs and interpretations. The flag is also often seen in movies, television shows and video games that feature pirates.

The Calico Jack flag was even adopted by the US Army’s 82nd Airborne Division during World War II, as a symbol of their mission to “strike with speed”. Since then, it has become a popular military insignia and is often worn by soldiers to signify their bravery and courage.

The Calico Jack flag remains a popular and iconic symbol of piracy and rebellion, and its unique design and history continue to captivate pirate enthusiasts and casual onlookers alike.

The Blackbeard Flag

The Blackbeard Flag, also known as the “Edward Teach Flag,” is one of the most recognizable pirate flags to date. This flag, which was used by the infamous pirate Blackbeard, featured a devil holding a spear, which seemed to poke the heart of a bleeding figure. According to historians, this flag was designed to intimidate enemies, and it certainly did that job well.

The color scheme of the Blackbeard Flag was also significant, as it featured a black background which symbolized death and destruction. The devil on the flag represented Blackbeard himself, who was known for his fierce and ruthless nature. The heart represented Blackbeard’s enemies, who he aimed to strike fear into with this flag.

Blackbeard’s flag was a clear indication of his intentions, as it was designed to strike fear into the hearts of his enemies. Interestingly, it is believed that the skull and crossbones flag, which is widely associated with pirates, was not commonly used during Blackbeard’s time.

Despite its menacing appearance, the Blackbeard Flag was not very complex in design. However, its simplicity added to its effectiveness, as it was easy to reproduce and display on various surfaces such as sails or hats. It also helped distinguish Blackbeard from other pirates, as many of them used similar flags.

The Blackbeard Flag served as a symbol of terror for many years and is still recognized today as a representation of piracy. Although Blackbeard met his demise in 1718, his legacy and flag continue to fascinate many people to this day.

To summarize, the Blackbeard Flag was a symbol of terror used by the infamous pirate Blackbeard to intimidate his enemies. With its menacing design, color scheme, and simplicity, it was highly effective in doing so. Its legacy as a representation of piracy continues to this day.

The Rackham Flag

The Rackham flag, also known as the “Calico Jack” flag is one of the most recognizable pirate flags in history. This famous flag features a skull with crossed swords, set on a black background with two hearts below it. It was flown by the pirate Calico Jack Rackham during his brief but successful career as a pirate.

Calico Jack was known for his ruthless tactics and his penchant for violence, all of which were reflected in the design of his flag. At the time, pirates often used their flags to send messages to their victims. The skull and crossed swords symbolized death, while the two hearts below it were interpreted as a symbol of the pirate’s love for danger and adventure.

The Rackham flag was first seen in the Caribbean in the early 18th century, and it quickly became a popular symbol among pirates. Its fame was cemented when Anne Bonny and Mary Read, two of Rackham’s crew members, were arrested and sentenced to death. According to legend, Rackham told the judge, “if he had fought like a man he need not have been hang’d like a dog,” further solidifying the flag’s notoriety.

Today, the Rackham flag remains one of the most famous pirate flags in history. Its design has been used in countless movies, TV shows, and video games, and it continues to inspire fear and awe in those who see it. Despite the flag’s association with piracy and violence, it has become a beloved symbol of adventure and rebellion, making it an enduring and iconic image in popular culture.

Later Pirate Flags

Later Pirate Flags
During the later years of piracy, several new pirate flags were designed to represent various crews. One of the most famous was the flag of Bartholomew Roberts, which showcased a figure of Death holding an hourglass with the inscription “Avaunt” (meaning “begone” or “go away”) above it. Another popular flag was that of Emanuel Wynne, which featured a human skull atop crossed bones with the letters “S.P.R” underneath (likely standing for “Surrender the Prize” or “Surrender Poor Rogues”). The flag of Stede Bonnet showcased a skull with an hourglass and the inscription “Our Time is Short,” while also prominently featuring a heart with an arrow through it. These later pirate flags continued the tradition of using ominous symbols and motifs such as skulls, bones, and Death personified.

The Flag of Bart Roberts

The Flag of Bart Roberts was unique and distinctive due to its design and the interesting message it conveyed. Bart Roberts was one of the most successful pirates of the Golden Age, and his flag represented his fierce reputation on the seas.

The flag featured a skull with crossed swords beneath, while on the top was an hourglass with wings. The skull represented death, while the swords represented the pirate’s willingness to fight and defend themselves. The hourglass symbolized that time was running out, and life was fleeting, so they needed to make the most of each moment.

Roberts understood that life was short, and he wanted to convey this message with his flag. The hourglass and wings showed that he and his crew were always on the move and never wasted a moment. This flag was a clear indication that they were ready to fight till the last breath, living their lives to the fullest.

Roberts was known for his philosophical leanings, and his flag was a symbol of his beliefs. The hourglass and skull together represented the idea that death comes to all, no matter who they are. The crossed bones under the skull were also a reminder of mortality, but with the swords, it represented the fight to overcome death.

The Flag of Bart Roberts was a unique combination of death, time, and philosophy. It represented the pirate’s fierce and uncompromising attitude towards life, and that death was inevitable. His flag was one of the most recognizable in pirate history, and it is a testament to his legacy as one of the greatest pirates of the Golden Age.

The Emanuel Wynne Flag

The Emanuel Wynne Flag is another famous pirate flag that was used during the Golden Age of Piracy. This flag was named after Captain Emanuel Wynne, who was known to have sailed as a pirate during the early 18th century. The flag features a skull and crossbones, along with an hourglass which was a symbol of the pirate’s mortality.

This flag was unique in that it had a red background, which was unusual for pirate flags at the time. The red color was likely chosen to symbolize danger or warning to other ships. This flag was also known to have been flown by other famous pirates such as Edward Low and Francis Spriggs.

The inclusion of the hourglass was a stark reminder to all who saw it that time was running out, not only for the pirates but also for their intended victims. The skull and crossbones was a universal symbol of danger and death. Together, these elements created a fearsome flag that struck fear into the hearts of those who saw it.

The Emanuel Wynne Flag was a testament to the creativity and ingenuity of pirates during the 18th century. It showed that pirates were not just bands of lawless miscreants but could also be cunning and strategic in their approach to piracy. The symbolic elements of the flag were carefully chosen to convey a message of danger and mortality, which added to the mystique and legend of the pirates.

Today, the Emanuel Wynne Flag remains a popular pirate symbol and has been used in various pirate-themed merchandise and entertainment. Pirates continue to capture the imagination of people around the world, and the flag serves as a reminder of the daring and adventurous spirit of the Golden Age of Piracy.

The Stede Bonnet Flag

The **Stede Bonnet Flag** is one of the most interesting pirate flags of the early 18th century, largely due to its unique design. Unlike the majority of pirate flags, which featured symbols such as skulls and crossbones, the Stede Bonnet flag was emblazoned with a **man standing with a sword in hand**. The sword is pointing up, suggesting a willingness to engage in combat. This has led many historians to believe that the design of the Stede Bonnet flag is a reflection of Bonnet’s desire to be seen as a gentleman pirate.

Stede Bonnet, also known as the “Gentleman Pirate,” was a wealthy landowner from Barbados who turned to piracy in 1717. Bonnet’s decision to become a pirate was likely fueled by a midlife crisis and a desire to escape his unhappy marriage. Unlike most pirates, Bonnet had no experience at sea and quickly gained a reputation as an incompetent leader. Despite this, his unique flag design helped to cement his place in the history of piracy.

The Stede Bonnet flag was flown by Bonnet and his crew during several successful pirate raids. However, the flag did not bring Bonnet the respect he craved, and he eventually fell out of favor with his crew. In September 1718, Bonnet was captured and taken to Charleston, South Carolina, where he was imprisoned and eventually hanged.

Today, the Stede Bonnet flag remains a popular symbol of piracy and is often featured in movies, TV shows, and video games. The flag’s unique design and association with a wealthy landowner-turned-pirate make it a popular choice among fans of pirate lore.

Modern Interpretations of Pirate Flags

In modern times, pirate flags have taken on new meanings and interpretations. One such example is the use of the Jolly Roger by hacker groups and online activists. The skull and crossbones symbolize the fight against authority and the desire for freedom. The flag of the Pirate Party, a political party in several countries, also draws inspiration from traditional pirate flags. The party advocates for digital rights, freedom of information, and greater government transparency. The use of pirate flags in popular culture has also led to a surge in merchandise featuring the iconic symbols. From t-shirts to phone cases, the Jolly Roger has become a trendy fashion statement for those looking to add a rebellious edge to their style. These modern interpretations show that pirate flags continue to hold a place in contemporary society as symbols of resistance and individualism.

The Flag of the Pirate Party

The pirate flag has become a popular symbol that signifies rebellion and freedom. It has even inspired political parties, such as the Pirate Party, to use variations of the Jolly Roger for their flag. The Pirate Party is an international political organization that promotes freedom of information, transparency, and privacy rights.

The flag of the Pirate Party typically features a skull and crossbones, sometimes with a cutlass or other weapon included. The skull and crossbones are often depicted in colors such as purple or orange, giving the flag a modern look that sets it apart from traditional pirate flags.

Interestingly, the Pirate Party’s flag is often seen flying at political rallies and events, making it a striking and instantly recognizable symbol of social and political activism. The use of the skull and crossbones represents a rejection of traditional authority and a call for change.

In recent years, the Pirate Party has gained considerable attention and support in countries around the world, including Germany, Sweden, and Iceland. The party’s platform on digital rights and Internet privacy has struck a chord with many, particularly young people who are increasingly concerned about online security and surveillance.

The flag of the Pirate Party is a powerful emblem of political resistance and dissent, and its bold design and modern colors reflect the party’s commitment to innovation and progress.

The Jolly Roger in Popular Culture

The Jolly Roger pirate flag has become an iconic symbol in popular culture. It has been featured in numerous movies, TV shows, video games, and even on merchandise such as t-shirts and posters. One of the most popular depictions of the Jolly Roger in popular culture is the portrayal of pirates with black eyepatches, wooden legs, and parrots on their shoulders.

However, not all depictions of the Jolly Roger in popular culture are accurate. Some portrayals show the flag as having a skull with crossed pistols or swords, instead of the traditional skull and crossbones. The use of the Jolly Roger as a symbol of rebellion and nonconformity has also become popular in certain subcultures, such as punk and goth.

One famous example of the Jolly Roger in popular culture is the Pirates of the Caribbean movie franchise. The main character, Captain Jack Sparrow, is often seen brandishing the flag and even uses it to escape danger in a few scenes throughout the series. The Jolly Roger also appears in the logo of the Pittsburgh Pirates baseball team, as well as on the uniforms of some sports teams.

Another popular use of the Jolly Roger in modern times is as a symbol of piracy in the digital age. The flag has been used by various groups advocating for internet freedom, such as the Pirate Bay file-sharing website. The Jolly Roger has also been adopted by the Pirate Party, a political party with a focus on digital rights and civil liberties.

Despite its varied uses in popular culture, the Jolly Roger remains a powerful symbol of adventure, rebellion, and piracy. Its widespread recognition and association with high-seas adventure have cemented its place in both history and modern popular culture.


As we can see, the evolution of pirate flags throughout history is a fascinating subject. From the early days of piracy to the present, pirate flags have always been an iconic symbol of the pirate lifestyle. The different designs and meanings behind the flags show the progression of piracy and the changing pirate culture throughout history.

The Jolly Roger remains the most recognizable pirate flag, even today. Its design has been reproduced in countless movies and TV shows, making it the quintessential pirate symbol. However, as we have seen, the Jolly Roger was just one of many different flags flown by pirates throughout history.

The Golden Age of Piracy saw the emergence of some of the most famous pirate flags, such as the Blackbeard Flag and the Calico Jack Flag. These flags represented the individuality and independence of pirates during this time, showcasing their unique personalities and personal beliefs.

In the later years of piracy, flags became more standardized, as pirates began to form alliances and work together. However, pirate flags still remained an important symbol of the pirate way of life.

In modern times, the Jolly Roger has taken on new meanings. It has become a symbol of rebellion and anti-establishment thinking. The Flag of the Pirate Party is also an example of how pirate flags have been adapted to fit with modern political ideologies.

In conclusion, pirate flags have a rich and complex history, reflecting the changing nature of piracy throughout the years. The iconic Jolly Roger may be the most well-known pirate flag, but the history of piracy is filled with many different designs and motifs. From the early days of piracy to the present, pirate flags have remained an important symbol of the pirate lifestyle, embodying the rebellious and individualistic spirit of piracy.

Frequently Asked Questions

What is the Jolly Roger?

The Jolly Roger is a famous pirate flag that dates back to the early 1700s. It was typically depicted as a white skull and crossbones on a black background.

Why did pirates use flags?

Pirates used flags to intimidate their victims and send a message of their reputation and strength. It was also useful to identify friendly ships and to differentiate between pirates from different crews.

What does the red flag represent?

The red flag was used to signify that no mercy would be shown to those who were captured. It was considered a warning of bloody consequences.

What is the black flag?

The black flag was used by pirates to indicate that they intended to attack and capture a ship. This was a signal to prepare for battle.

Who was Queen Anne’s Revenge?

Queen Anne’s Revenge was the flagship of the infamous pirate Blackbeard. The ship’s flag was a white skull with an hourglass, indicating that time was running out for those who crossed Blackbeard.

What is the Calico Jack flag?

The Calico Jack flag featured a skull with crossed swords underneath. This pirate was known for his flamboyant style and distinctive flag.

What was Blackbeard’s flag?

Blackbeard’s flag was a black background with a white skeleton holding a spear. This was a frightening image that struck terror into victims.

What was the Rackham flag?

The Rackham flag featured a skull with crossed swords and an hourglass, similar to the Queen Anne’s Revenge flag. It was used by pirate Calico Jack Rackham and his crew.

What was the Pirate Party flag?

The Pirate Party flag is a modern interpretation of a pirate flag, used by a political party advocating for internet freedom and digital privacy. It features a black flag with a white pirate skull wearing a headband with the letter P on it.

What are some popular culture references to the Jolly Roger?

The Jolly Roger has been featured in many popular culture references, such as in the movie “Pirates of the Caribbean” and as the logo for the Pittsburgh Pirates baseball team.


Leave a Comment