Jolly Roger Flags

Jolly Roger History

The use of “Jolly Roger” flags have been traced back to the 1700’s in what was considered to be the “Golden Age” of piracy. The term “Jolly Roger” has no definite origin but most scholars believe it comes from the term “jolie rouge” – a French term for “pretty red”. Pretty red refers to the red flags originally flown by pirates to indicate that there was “no vacancy” on the ship. Black flags were originally flown to indicate mercy would not be given to overtaken ships.

It is believed that Emanuel Wynn was the first pirate to use a “skull and crossbones” design, which has become the most common depiction, somewhere at the beginning of the 1700’s which eventually led to many other pirates creating their own Jolly Roger flags. These flags were designed to intimidate the crews of ships that the pirates were to overtake. This often led to many captains surrendering their ships without a battle at all. The flags displayed to other ships that the pirates were not bound by the common laws of engagement.

Many different elements could be added to the flags to signal different meanings. For example, an hourglass on the flag meant that the victims’ time was running out; a cup or chalice signaled that the pirates often toasted the devil; handshakes between a skeleton and person indicated making deals with the devil; stabbing hearts meant they would attack to end the lives of opponents:

Emmanuel Wynne flag featuring hourglass design

Bartholomew Roberts making deal with the devil

Walter Kennedy featuring chalice toast to the devil

They have since become the main symbol for piracy and can be seen in television and movies of today.

The Most Famous Jolly Roger Flags


Skull and Crossbones:
The Skull and Crossbones design has been used by many pirates and is the most common “Jolly Roger” design of our day. Many pirates used variations of this design, including “Black Sam” Bellamy, Stede Bonnet, Christopher Condent, Henry Every and Emanuel Wynne.



Edward Teach:
Edward Teach (Blackbeard)-Edward Teach, better known as Blackbeard, flew this flag from his ship Queen Anne’s Revenge between 1717 and 1718. His name referred to the long, thick beard and dark demeanor which he carried. Even though Teach did not become the “most successful” pirate, he has become the most famous due to stories and folklore regarding his life and death. The flag features a skeleton stabbing a heart which is carrying a chalice in the other hand. The chalice is meant to show that he is giving a toast to the devil.



Jack Rackham (Calico Jack):
Jack Rackham (Calico Jack)-A Caribbean pirate from 1717-1720, Calico Jack became famous for two different reasons. Jack designed the now famous skull and swords Jolly Roger flag and he allowed female pirates onto his ships, including two of the most famous female pirates: Mary Read & Anne Bonny. He captained the “Kingston” which originally was a Jamaican ship which he captured. His skull and crossed swords design is still used in one of the two most common Jolly Roger designs.