10 Famous Pirate Flags: A Visual History

10 Famous Pirate Flags: A Visual History

Pirates have captured the imagination for centuries, both in history and in pop culture. One enduring symbol of piracy is the pirates’ distinctive flags, most notably the Skull and Crossbones or “Jolly Roger.” Pirate flags, often referred to as Jolly Rogers, are some of the most iconic symbols of the Golden Age of Piracy.

These flags were used by pirates to identify themselves to other ships and to intimidate their prey. While there were many different pirate flags in use. Here is a some of of 10 of the most famous pirate flags and the stories behind them:

1. Traditional Jolly Roger Flag

Dudaweyll, CC BY-SA 4.0, via Wikimedia Commons

The classic pirate flag is a white skull over crossed bones on a black background. The use of this flag by pirates dates back to the early 18th century Golden Age of Piracy. Though associated with all pirates, the design was particularly used by pirates operating in the Caribbean and Atlantic.

The origin of the name “Jolly Roger” is disputed, with possible sources being the French joli rouge (“pretty red”) referring to blood, or “Old Roger” as a term for the devil. Whatever its etymology, the pirate flag sent a clear warning – surrender or face the consequences!

2. The Blackbeard Flag

RootOfAllLight, CC BY-SA 4.0, via Wikimedia Commons

Edward Teach, better known as Blackbeard, became one of history’s most feared pirates in the early 1700s. He commanded four ships and a crew of 300 at the height of his raiding. He came up with his own make of a flag which featured a horned skeleton holding an hourglass in one hand and a spear pointing towards a bleeding heart in the other.

This gruesome flag reinforced Blackbeard’s menacing reputation. He cultivated a fierce image with braided hair and pistols strapped across his chest. According to legend, Blackbeard lit hemp cord in his hair and beard to appear more demonic in battle. It has since become one of the most famous pirate flags in history.

3. Calico Jack Rackham Flag

Pirate_Flag_of_Jack_Rackham.svg: User:EugeneZelenkoderivative work: HAF 932, CC0, via Wikimedia Commons

Next on our list of the most famous pirate flags is the “Calico Jack Rackham” which was used by an English pirate from the 1700s,known as Jack Rackham. Rackham is remembered for two things – his flamboyant fashion sense and having two female crew members. His nickname “Calico Jack” likely came from his colorful calico clothing.

Rackham’s Jolly Roger featured a skull with crossed swords beneath it, an hourglass beneath that, and a bottom banner reading “Time flies.” This design incorporated common pirate symbols representing death and time running out for their prey. Rackham’s pirate career ended swiftly when he was captured by pirate hunter Jonathan Barnet in 1720.

4. Black Bart’s Flag

RootOfAllLight, CC BY-SA 4.0, via Wikimedia Commons

Bartholomew Roberts also Known as Black Bart’s flag is also one of the most famous pirate flags. The  Welsh pirate Bartholomew Roberts was successful in plundering over 400 ships. His most notable Jolly Roger featured a skeleton holding an hourglass in one hand and arrows symbolizing death in the other.

The background was faded black rather than stark black, giving it an eerie ghostly appearance. This symbolized the inevitability of death and the swift passage of time, striking fear into those who saw it flying high. Roberts and his crew are also credited with pioneering the classic Skull and Crossbones design. He was killed in action against British forces off the coast of Africa in 1722. 

5. Stede Bonnet’s Flag

Charles Johnson, Public domain, via Wikimedia Commons

Stede Bonnet was an unlikely pirate, having been a wealthy landowner before turning to a life of piracy seemingly on a whim. Bonnet’s Jolly Roger featured a skull above a horizontal long bone with a heart. He was nicknamed the “Gentleman Pirate” due to his atypical background.He deviated from the typical designs of pirate flags.

His flag featured a white skull wearing a red bonnet and a long earring, adding a touch of eccentricity to the traditional pirate symbol. Bonnet eventually teamed up with Blackbeard for voyages along the Atlantic coast. He was captured and hanged in Charleston, South Carolina in 1718.

6. Edward Low’s Flag

RootOfAllLight, CC BY-SA 4.0, via Wikimedia Commons

A British pirate infamously known for his cruelty, Edward Low started his piracy career later than most, in his mid-30s. His Jolly Roger depicted a red skeleton stabbing a heart with a spear. This flag clearly demonstrated Low’s penchant for brutality. He subjected victims to gruesome tortures such as cutting off ears and pouring hot wax or burning sulfur on bare flesh.

The red skeleton flag was effectively used to instill fear in potential prey. Merchants and ships would quickly surrender once they recognized Low’s distinctively cruel Jolly Roger flag. For many, the flag represented a fate worse than death. Captured by French forces in 1724, Low was hanged after refusing to reveal the location of his treasure hoard.

7. Black Caesar’s Flag

Geo. S. Harris and Sons, CC0, via Wikimedia Commons

Black Caesar, a legendary African pirate, used a flag that featured a black man holding a spear, representing his African heritage and his determination to fight against oppression. This flag became a symbol of resistance and freedom for many enslaved Africans who joined his crew.

Black Caesar’s flag is a variation of the Jolly Roger flag. It features a skull and crossbones above two crossed swords, but it also has a heart below the skull and crossbones. The heart is believed to represent Blackbeard’s love for his two female crew members, Anne Bonny and Mary Read. Black Caesar’s flag is a reminder of Blackbeard’s power and ruthlessness. It is also a symbol of his love for his crew members.

8. William Kidd’s Flag

Jean Leon Gerome Ferris, Public domain, via Wikimedia Commons

William Kidd was a Scottish sailor who turned to piracy late in the 17th century. He used several different pirate flags during his exploits on the Indian Ocean and Red Sea. His most notable flag featured an arm holding a sword and dripping blood. The arm wielding a bloody sword was meant as a clear threat of violence to potential prey. It signified that resistance would be met with death.

This was in line with Kidd’s reputation as a pirate who would kill captives if provoked. The flag’s background varied – sometimes plain red or sometimes white or black flags with the red arm and sword. The latter version closely resembled flags used by French privateers at the time. This may have been an attempt by Kidd to blur the lines between pirate and legitimate privateer.

9. Anne Bonny’s Flag

RootOfAllLight, CC BY-SA 4.0, via Wikimedia Commons

Another famous flag used by pirates is the Anne Bonny‘s flag. She is one of the most famous female pirates in history. She sailed with captain “Calico Jack” Rackham and fellow female pirate Mary Read in the early 18th century. Bonny used a distinctive Jolly Roger flag that featured a skull with crossed swords below it, which was the common symbol used by Calico Jack’s crew.

What made Bonny’s flag unique was the addition of a woman’s head with flowing hair on one side of the flag. The female head is believed to represent Bonny herself, incorporating her infamy as a female pirate raiding alongside the men. It was highly unusual for women to become pirates during this era, so Bonny’s inclusion of a woman on her flag was a bold statement about her unconventional role.

10. John Phillips’ Flag

RootOfAllLight, CC BY-SA 4.0, via Wikimedia Commons

John Phillips began his seafaring career as a carpenter’s mate on a British privateer during the War of Spanish Succession. Turning to piracy around 1721, he led raids along the African coastline before sailing for the Caribbean. His Jolly Roger design featured a skeleton and bleeding heart, with the words “Both or None” written beneath. The meaning of this phrase remains unclear, with theories ranging from referring to treasure or no mercy given.

The shield on Phillips’ flag is a symbol of strength and protection. It represents the fact that Phillips and his crew are well-armed and well-defended. The heart on Phillips’ flag is pierced by a bloody lance. This is a symbol of love and loss. It is believed to represent the love that Phillips had for his family and the loss of his life at sea. Phillips died of fever in 1724 off the coast of Hispaniola, leaving his enriched followers to continue his exploits.

In conclusion all these flags left a lasting legacy and the lasting legacy of colorful Jolly Roger flags is a testament to both the romantic lore and grim reality of the Golden Age pirates. Both feared and celebrated, pirates left an indelible mark through their bold adventures and Symbolic flags warning foes to surrender or suffer dire consequences. Jolly Roger flags continue to capture popular imagination and emblem the rebellious, free-wheeling spirit of piracy.