Flying Jolly Roger Pirate Flag

Pirate Flags - Symbols of Terror on the High Seas

The flags of history’s most notorious pirates, and why they flew them.

The mere sight of a pirate flag has been enough to strike fear into the hearts of sailors and coastal dwellers throughout history. These iconic symbols, with their sinister imagery and unmistakable message, have come to define the very essence of piracy. This article will delve into the fascinating story of pirate flags, exploring their origins, the meaning behind their designs, and the ways in which they were used to terrorize and manipulate their victims.

What is the most famous pirate flag?

The use of pirate flags can be traced back to the late 17th and early 18th centuries, during the Golden Age of Piracy. The term "Jolly Roger" is believed to be derived from the French phrase "joli rouge," meaning "pretty red," a reference to the blood-red flags flown by privateers in the early 17th century. These red flags were a symbol of defiance and a declaration of no mercy, signaling that no quarter would be given to any captured enemy.

As piracy evolved, so did the flags that these maritime outlaws flew. Pirates sought to distinguish themselves from privateers and create their own unique symbols of terror. The Jolly Roger transformed from a simple red flag into the distinctive black flag adorned with menacing symbols that have become synonymous with piracy.

What was the original pirate flag?

Symbolism and Design: Pirate flags often featured macabre imagery designed to instill fear in their victims. The most iconic design consists of a white skull and crossbones set against a black background, a simple yet chilling symbol of death. However, the world of pirate flags was far more diverse, with many notorious pirates creating their own unique designs.

Some flags incorporated additional elements such as swords, hourglasses, and bleeding hearts, each with their own symbolic meaning. Swords represented violence and combat, while hourglasses symbolized the fleeting nature of time and the urgency for victims to surrender. Bleeding hearts, on the other hand, were a warning that no mercy would be shown.

Tactics and Usage

Pirate flags were not only symbols of terror but also served as tactical tools in the hands of cunning pirates. One of the most common strategies employed by pirates was to fly a false flag, often that of a friendly or neutral nation, in order to approach their target unnoticed. Once they were close enough, pirates would then hoist the Jolly Roger, revealing their true identity and striking fear into the hearts of their victims.

This tactic allowed pirates to capitalize on the element of surprise and minimize the risk of resistance. The sight of the dreaded pirate flag often prompted ships to surrender without a fight, allowing pirates to take their prizes with ease.

Famous Pirates and their flags.

What was Blackbeard's actual flag?

Blackbeard Flag
Edward Teach (Blackbeard): Blackbeard's flag featured a white horned skeleton holding an hourglass in one hand, symbolizing that time was running out for his victims. The skeleton was also depicted stabbing a bleeding heart with a spear, indicating no mercy would be shown. BUY FLAG
Calico Jack Flag
"Calico Jack" Rackham: John Rackham, known as "Calico Jack," had a flag with a white skull and crossed swords on a black background. The crossed swords emphasized his crew's readiness for combat.
Captain Kidd flag
William Kidd: Captain Kidd's flag displayed a white skull with two crossed bones beneath it, set against a black background. This design closely resembles the iconic Jolly Roger and is among the most well-known pirate flags.
Thomas Tew flag
Thomas Tew: Tew's flag featured a white arm holding a cutlass on a black background, symbolizing the violent nature of piracy and the readiness of his crew to engage in combat. Onlookers be warned: we will fight to the death.
Black Bart Flag
Bartholomew Roberts (Black Bart): Black Bart flew a number of different flags during his career as a pirate. One was described in Johnson's General History as, "The Flag had a Death in 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."
Stede Bonnet Flag
Stede Bonnet: Known as the "Gentleman Pirate," Bonnet's flag displayed a white skull with a long bone beneath it, set against a black background. A heart pierced by a dagger was situated between the skull and the bone, symbolizing a violent end for those who opposed him.
Edward Low Flag
Edward Low: Low's flag featured a red skeletal figure on a black background, holding an hourglass in one hand and a dart pointed at a heart dripping blood in the other. This imagery was designed to terrify potential victims and convey a sense of impending doom.


The story of pirate flags is one of intrigue, terror, and cunning tactics. From their origins as blood-red declarations of defiance to the iconic skull and crossbones, pirate flags have evolved into powerful symbols of piracy that continue to captivate our imaginations. The strategic use of these flags allowed pirates to exploit fear and deception, seizing their prey with minimal resistance. Today, the Jolly Roger stands as an enduring testament to the ruthless and cunning nature of pirates, a symbol that will forever be associated with the thrilling world of high-seas adventure and maritime outlaws.