The Jolly Roger with its white skull and crossbones set against a black background has become a rather jovial part of pirate folklore but, in its day, this flag and others with similar blood-curdling designs, had a single and terrifying purpose. The raising of the pirates’ flag, usually only hoisted at the last minute, signalled that the ship under approach should immediately surrender or face not only attack and boarding but the execution of all on board. The threat that no quarter was to be given was often reinforced by raising an additional flag, an all-red one. Pirates flew many other types of flags to signal their terrible purpose in approaching a ship, usually with gruesome imagery like skeletons, swords, and bleeding hearts. National flags were also used, often as a ruse to disguise the pirates’ intention to plunder and murder.
The Jolly Roger
The term 'Jolly Roger' originally referred to any sort of flag raised by pirates and privateers (state-sponsored pirates) and designs certainly varied. The name 'Jolly Roger' has since come to signify one particular type of pirate flag: a black background with a white human skull set above two crossed bones, also in white. The origin of the name is not known for certain, but it may derive from the word 'Roger' which in that period signified the Devil, a figure often referred to as 'Old Roger'. A group of pirates hanged in Newport, Rhode Island in 1723 had called their flag showing a skeleton holding an hourglass and a bleeding heart as 'Old Roger'. The term 'roger' was also applied to wandering beggars or vagrants and privateers were sometimes referred to as 'Sea Beggars', particularly in the Netherlands. An alternative origin is the French term le jolie rouge (the "pretty red"), which was applied to the red flag commonly flown by privateers for centuries. Another possible origin (and there are many), is the Welsh pirate Black Bart Roberts (aka Bartholomew Roberts, c. 1682-1722) who was so famous for wearing bright red silks in battle that the French also nicknamed him le jolie rouge. Roberts was known to fly the skull and crossbones flag, amongst others on his fleet of ships and so this flag became the 'Jolly Roger' by association.
Although pirates and other mariners may have used skulls and bones on flags much earlier in history, the first recorded use of a Jolly Roger 'black flag' is on the ship of Emmanuel Wynne, a Breton pirate who used a skull, crossbones, and hourglass design in an engagement in 1700 off Santiago. Despite Wynne’s use of it, the Jolly Roger was really only used with regularity by British and American pirates in the first quarter of the 18th century and then after the plain black flag had already been in common use for about a century. Christopher Condent, who plundered the Caribbean and Pacific between 1668 and 1672, had perhaps an early version of the Jolly Roger with three skulls and matching sets of crossed bones. The British pirate Richard Worley (hanged in Charleston in 1718) flew a version with the skull superimposed on top of the crossbones. Edward England, who operated in the Caribbean between 1717 and 1720, was known to have flown the Jolly Roger in the form we would recognise today (he also simultaneously flew the Union Jack and a red flag for good measure). Henry Jennings, an English pirate active in the Caribbean and Atlantic from 1715 to 1717, was another who flew the now-classic Jolly Roger.
Certainly, the meaning of the black flag, in particular, and by extension the Jolly Roger, was known to most law-abiding captains. One captain Snelgrave reported in 1719 that the Jolly Roger "is intended to frighten honest merchantmen into surrender on penalty of being murdered if they do not" (Rogozinski, 174). It may be that the Jolly Roger was intended as a first warning, and if not heeded, the hoisting of a red flag indicated that no quarter would be given. This is certainly how the two flags were used by the pirate ship which attacked one Captain Richard Hawkins, an episode he recorded in a letter of 1724.
Despite its rather brief use in practice, the Jolly Roger has firmly established itself into the popular imagination thanks to its appearance in celebrated pirate stories like R. M. Ballantyne’s 1858 novel The Coral Island and Robert Louis Stevenson’s Treasure Island, first published as a magazine serial in 1881 and as a novel in 1883. In both books, the main pirate vessel flies the Jolly Roger and it is recognised by all for its significance. The flag then gained even further prominence following countless appearances in Hollywood films from silent movies to 21st-century blockbusters.
Pirates were nothing if not colourful individuals and so it should come as no surprise that they often wanted a flag that was unique to themselves. The most common background of a pirate’s flag was black or red and the images on them were to remind victims of the dreadful consequences of resistance. Skeletons, skulls, a bloody heart, an hourglass (signifying one’s time on this earth was coming to an imminent close), and wings (one’s time was flying away) were all common designs on flags. As many of these symbols were frequently seen, too, on gravestones of the period, everybody knew what they meant. Weapons were another favourite symbol, such as swords, curved-bladed cutlasses, flaming cannonballs, and spears. For example, the English pirate John Rackham (d. 1720), whose nickname was ‘Calico Jack’, famously sported a black flag with a white skull above two crossed cutlasses on his ships which plundered the Atlantic and Caribbean.
Henry Every, a British pirate active in the Red Sea and Atlantic between 1692 and 1695, had a human body on his flag with the figure holding an hourglass in one hand and a heart bleeding from a spear wound in the other. The most famous pirate of all, Edward Teach ('Blackbeard', d. 1718), at least according to legend, had a similar flag but made it more frightful by changing the body to a skeleton. Black Bart Roberts went for a more amusing flag, which showed him drinking a cup of wine with a skeleton or devil grasping a burning spear. Pirates were not above a bit of self-promotion, either. Roberts’ personal banner showed him with a sword and standing on top of two skulls. Under the skulls were the letters ABH and AMH, signifying that they represented the decapitated heads of the governors of Barbados and Martinique respectively ("A Barbadian Head" and "A Martiniquan Head"), both of whom sent ships in pursuit of Roberts. Finally, some pirates seem to have had difficulty in deciding which symbol to use on their flag and so rather cluttered ensembles were created such as one attributed (perhaps incorrectly) to Christopher Moody, which included a skull, crossbones, a sword, and an hourglass with wings, all on a red background.
Coloured & National Flags
Flags might also be used for the pirates’ own communications. The great Chinese pirate Cheng I (aka Zheng Yi, l. 1765-1807) terrorised the seas of East Asia from Vietnam to Hong Kong. Cheng eventually headed an alliance of six Asian pirate leaders from 1801, and each of the commanders’ fleets hoisted a coloured flag to differentiate themselves. The colours employed were red, black, white, green, blue, and yellow. In addition, each flag was a different shape. Each commander operated in a particular area, but the use of the flags ensured no confusion came about when enemy ships sailed across zones of attack.
Some pirates flew the flag of their principal sponsor, either a family flag or a national one. The use of national flags was also an attempt to provide a wafer-thin veneer of respectability to the actions of pirates who saw themselves more as privateers and legitimate enemies of their sovereign’s own enemies. In 1694, the British Admiralty obliged all privateers operating in the Crown’s name to fly a red flag, 'The Red Jack' besides a national flag. In the 18th century, American privateers tended to fly a red flag with horizontal white stripes.
Some organisations like the Barbary States of North Africa and the Knights of Malta (aka the Knights Hospitaller) who targeted Muslim merchant vessels insisted pirates working for them flew their flag. Other captains were proud of their nationality and flew a suitable flag, such as the corsair/privateer Hamidou Reis (1790-1815) who operated in the Mediterranean and sailed under an English flag.
Finally, some pirates used ordinary national flags to fool their victims. One famous captain to employ this ruse was the English pirate John Deane, who operated in the Caribbean in the 1670s. Dean would fly Dutch, Spanish, and French flags to lure his victims into a false sense of security. Sometimes the authorities used the same trick, as in the case of the American ships that raised English flags in 1815 and approached near enough to Hamidou Reis’ ship to fire a cannonball that cut the privateer in half. Clearly, for both sides, flags could be a deadly element in the sea battles which involved pirates and privateers.