Skull and Crossbones - Rubber hand stamps

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. 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.