Jolly roger depicting several different pirate symbols

Pirate Symbols and Their Meanings: More Than Just a Skull and Crossbones

Pirate symbols are the most enduring part of the Golden Age of Piracy, thanks largely to novels and movies. In an era when men had fanciful names like Calico Jack, Black Bart, and Blackbeard, it’s easy to imagine equally fanciful symbols adoring their flags. But which symbols were fact and which ones were works of fiction? 

Pirate Flags Were Powerful Pirate Symbols

Jolly roger used by pirate Ned Low
Jolly roger used by pirate Ned Low

Flags have become the most iconic pirate symbols in the modern world. But, in the heyday of Caribbean piracy, pirate flags conveyed a sinister meaning. Employing symbols connected with violence and death, pirate flags were used to instill fear in the hearts and minds of the crews they attacked. One captain noted in 1719 that a pirate flag “is intended to frighten honest merchantmen into surrender on penalty of being murdered if they do not.”

Pirates, however, flew more than one type of flag. Let’s breakdown the three main types of pirate flags and how they were used.

Black Pirate Flag

Black pirate flag

Pirate ships used a black flag to signal to an enemy vessel that they were about to attack, but that quarter would be given. This meant, essentially, the pirates would not kill everyone on board. How nice.

Black flags became, by far, the most used flag among pirates during the Golden Age of Piracy. So much so, in fact, that the term “black flag” became synonymous with “pirate” during this period. 

Pirates seemed to have chosen black as a flag color rather intentionally. In Western culture, the color black had long been associated with death (think, “the Black Death” in medieval Europe). 

By the end of the Golden Age of Piracy, simply hoisting a black flag was enough to draw the attention of naval officials. In 1726, Captain Delgarno of the English Royal Navy recorded that, while sailing in the Caribbean, he was “resolv’d to bring in all such pirates, where he shall find a black flag.”

Red Flag

Red pirate flag

While seeing a black flag was bad news, seeing a red flag was even worse. 

Pirate ships used a red flag to signal to an enemy vessel that no quarter would be given. If they did not surrender to the oncoming pirates, they could expect violence. 

Here again, pirates chose their colors well. In the Western mind, the color red has long been associated with blood (for obvious reasons). This connection between blood and the red pirate flag was so obvious to contemporaries that such flags became known as “bloody flags.” 

One seventeenth-century account of piracy notes that “when they [pirates] fight under the Jolly Roger, they give Quarter, which they do not when they fight under the Red or Bloody Flag.”

Jolly Roger Flags

Jolly roger of Bartholomew Roberts
Jolly roger of Bartholomew Roberts

Now this is where it gets fun. 

A jolly roger is what we think of when we imagine a classic pirate flag. A jolly roger flag consisted of a black or red background (though usually black) with a symbol that denoted violence. Anyone sailing the Caribbean during the Golden Age would have understood what these symbols meant (more on what these symbols were below).

The term “jolly roger” first appeared in the historical record in 1724 Charles Johnson’s book, A General History of the Pyrates. But how the term originated is a matter of some debate. Some historians believe it was derived from the French word for pirates’ red flags, “joli rouge.” Some say that it comes from a common eighteenth-century term for the devil: “Roger” or “Old Roger.” And one historian has said that it could be name for King Roger II of Sicily, a Templar who may have flow such a flag on his sea voyages.

Related: 13 Best Pirate Books for Swashbuckling History Lovers

No matter where the name came from, the first pirate flag matching the description of a jolly roger was noted in 1700. Flown by the pirate Emmauel Wynne, this jolly roger continued skull, crossbones, and hourglass designs.

Skull and Crossbones

Skull and crossbones pirate symbol
Skull and crossbones flag used by pirate Henry Every

The skull and crossbones symbol has a long history in Europe. As far back as the Middle Ages, people used a skull and crossbones to decorate graves, catacombs, and other funerary places.

The inspiration, interestingly enough, was originally religious. According to the Bible, Adam’s bones somehow came to rest at the base of Jesus’s cross. Due to this legend, skulls and “crossed bones” became a powerful symbol of funeral rites. 

Gravestone with a skull and crossbones
Early Modern gravestone with a skull and crossbones

When, several centuries later, Europeans hit the high seas during the Age of Exploration, ship captains began using the skull and crossbones symbol in their ledgers to denote that a member of the crew had died. Many pirates then took this well-known symbol of death and turned it into a symbol that emblazoned on their flags. 

When an enemy ship saw a jolly roger with a skull and crossbones, they knew they were in trouble.

Winged Hourglass

Skull and hourglass pirate symbols
Skull and hourglass jolly roger used by Captain Napin

We’ve all heard the phrase, “life is short.” It was even shorter in the seventeenth- and eighteenth-centuries, especially if you ran into a pirate. The hourglass as a pirate symbol is a not-so-subtle nod to this philosophy. 

  • The hourglass symbol meant that your time was running out and/or that your life would be short. 
  • The winged hourglass meant that the time you have left in life is flying away. 

We actually have records of several pirates using the hourglass symbol in their jolly roger. Pirate Francis Spriggs flew a flag with a “a large white Skeleton, with a dart in one hand, striking a bleeding Heart, and in the other an Hour Glass.”

According to A General History of the Pyrate, Bartholomew Roberts was once so mad at the governors of  “Barbadoes and Martinico” for issuing a warrant for his arrest that he hoisted a: 

“black Silk Flag flying at their Mizen-Peek, and a Jack and Pendant of the same: The Flag had a Death’s Head on it, with an Hour-Glass in one Hand, and cross Bones in the other, a Dart by it, and underneath a Heart dropping three Drops of Blood – The Jack had a Man pourtrayíd in it, with a flaming Sword in his Hand, and standing on two Skulls, subscribed A.B.H. and A.M.H. i.e. a Barbadian’s and a Martincan’s Head.”

Two Crossed Swords

Skull and crossed swords pirate symbols
Skull with crossed swords used by Jack Rackham

As far as pirate symbols go, swords may have been the most versatile. Swords have always been a symbol of power. This is one reason why surrendering generals, for centuries, handed over their sword to their victorious foe.

As a pirate symbol, swords were meant to communicate that a pirate captain and his crew were powerful and unafraid of violence. And, in pirate culture, it was common for new crew members to swear oaths upon a sword.

Two crossed swords took this symbol to another level. If a pirate ship had two crossed swords on their jolly roger, they were threatening their enemy with death in battle.

The famous pirate Jack “Calico Jack” Rackham used two crossed swords underneath a skull as his jolly roger.

Skeletons as Pirate Symbols

In the world of pirate symbols, a skeleton was the embodiment of death. Sometimes called the “king of death,” the eighteenth-century version of the grim reaper was a skeleton that would pierce a mortal in the heart with a spear and drag them to the land of dead. Creepy, right? 

The motif of a skeleton stabbing a heart proved popular among many pirates and was featured on quite a few jolly rogers (a few of which we’ve included in this post).

While a skeleton stabbing a heart was probably terrifying enough to most men aboard merchant ships that ran into a pirate ship, pirates didn’t stop there with their skeletal symbolism.

Horned Skeleton

Horned skeleton pirate symbol
Example of horned skeleton pirate symbol

Seeing a jolly roger with a horned skeleton was very bad news. 

This pirate symbol represented the devil himself. Pirates would have used a horned skeleton to tell enemy ships that their time had run out, Death himself had come to collect their souls, and that they could expect a slow, painful death.

Red Skeleton

Flag with red skeleton pirate symbol
Red skeleton flag flown by pirate Ned Low

Similar to its horned cousin, a red skeleton on a jolly roger connoted violence. When a pirate used a red skeleton on their flag, it meant that their enemies could expect a bloody, violent death.

Sources for Pirate Symbols and Their Meanings

  1. Mark Cartwright, “The Jolly Roger and Other Flags,”
  2. E.T. Fox, Jolly Rogers, the True History of Pirate Flags (Fox Historical, 2015), 31
  3. Fox, Jolly Rogers, the True History of Pirate Flags, 32
  4. “The Jolly Roger and Its Not-So-Merry Origins,”
  5. M.R. Reese, “The Ultimate Pirate Branding Symbol – The Origin of the Jolly Roger,”
  6. Cartwright, “The Jolly Roger and Other Flags,”
  7. Emily Miranker, “Pirates, Poison, and Professors: A Look at the Skull and Crossbones Symbol,”
  8. Peter T. Leeson, “Pirational Choice: The Economics of Infamous Pirate Practices,”
  9. Ibid
  10. Jamaica Rose and Michael Macleod, The Book of Pirates: A Guide to Plundering, Pillaging and Other Pursuits (Gibbs Smith: Layton, Utah, 2010), 140
  11. Ibid
  12. Fox, Jolly Rogers, the True History of Pirate Flags, 29
  13. Rose and Macleod, The Book of Pirates, 139

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