There are examples of various pirate flags belonging to certain pirate captains ranging from 1690 to 1722 - but most of the actual designs on them are artists impressions drawn from verbal or written statements surrounded by myth and contradiction, difficult to substantiate today at source. The flag flown in 1700 by the French pirate Emanuel Wynne in an engagement with HMS Poole of the Royal Navy is one of the earliest clearly described ; English pirate Captain Edward England also flew The Cross of St George flag but the pirate flag flown by him has come down to us as the archetypal ‘Jolly Roger’ through the mention of him by Long John Silver in the highly successful novel Treasure Island written by Robert Louis Stevenson and ‘stereotyped’ by many illustrators through publications of the book since 1880 as the ‘skull and crossbones’ flag used by pirates.

Pirates did adopt a particular flag aboard their ships to announce their intentions : but this flag - as you can see now popularly known as the ‘skull and crossbones’ - was not of a uniform design and came about through a steady process of individual development.

In ‘The Buccaneer Age’ of the mid to late 17^th Century, these men commonly flew their national colours (or the colours of the nation who had given them their commission as ‘privateers’) or each captain designed and created a simple pennant of his own design under which his own crew or group could muster and were not simply white-on-black but used a variety of colours. Since medieval times, flags have been flown or carried by companies of armed men and these flags spoke a language of their own. Used aboard ships, a flag was a declaration of national identity - and it is just a short step from this to also using them as ‘subterfuge’. A single warship prowling around enemy commerce or approaching battle could and would fly a flag other than their own to try and lure the ‘enemy’ into a false sense of security. Once an action had been joined, a ship would generally hoist its own national colours to avoid any accusation of not being ‘honourable’ in its intentions (in either success or failure). It was also well-established at that time that hoisting a ‘blood-red flag’ on sea or land before an engagement with your national colours signalled your intention to ‘give no quarter’ : in simple terms, you would accept no surrender and take no prisoners. This was a psychological threat to your enemy and didn’t necessarily mean that you wouldn’t take any prisoners and slaughter everyone in the intended action : indeed, your enemy might hoist their red flag in doing exactly the same thing in return to you.

The ‘bloody-red flag’ signalling this intention to their Spanish victims was used by buccaneers and in the early days of ‘The Golden Age of Piracy’ both these tactics were duly adopted by pirates. An approaching pirate ship might fly no colours when first seen to study the intended prize through a telescope : if the victim had few men on deck, appeared relatively unarmed or showed signs of panic, then the pirates would close in, hoisting their ‘pirate flag’ as both a declaration of intent and a warning. Most pirate flags had designs on them in white or red on a black background so as to be easily identifiable at sea : most of these designs incorporated the ‘pirate philosophy’ of the threat of imminent violence within a short space of time indicated in the form of skeletons, crossed-bones, skulls, bleeding-hearts, spears, darts, hour-glasses or swords - or in some cases, all these combined. This flag was intended to instil fear and panic and make the intended victim quickly ‘heave-to’ at once and prepare to be boarded, under the assumed offer of ‘receiving quarter’ if he did so immediately. If any resistance was shown or an attempted escape indicated, the pirates could back up their threat by hoisting a red flag in which instance the statement was that you’d had your warning and in choosing to ignore it, whatever then happened was your fault!

The term ‘Jolly Roger’ has passed into pirate lore and the term has become generally used in describing the black flag with the ‘skull and cross-bones’ as flown by pirates. The first mention of ‘Jolly Roger’ in a dictionary is in 1724 but it is mentioned earlier in a maritime account dated 1719. The first mention of a pirate ‘black flag’ is in 1700 though in the same account it is hinted that the ‘black flag’ was already known by repute as a banner flown by pirates. A slightly later account describes a similar flag flown by a pirate off Brazil in 1703 and in 1718, an account from a merchant captain attacked by pirates states “Captain Howell Davis came in the river with a Black flag showing, which said flag is intended to frighten honest merchantmen into surrender on the penalty of being murdered if they do not.”  In 1724, another account from a merchant captain captured by pirates states (‘they’ meaning ‘pirates’) “… when they fight under the Jolly Roger they give quarter, which they do not when they fight under the red or bloody flag.”

It is doubtful as hinted in several claims that the ‘red flag’ was dyed with the blood of previous victims; probably the flags were made using paint, red cloth or silk but the strong red dye from haematoxylum campeacheata (‘logwood’ or ‘blood-wood’) was pretty common in the Caribbean. The origin of the actual term ‘Jolly Roger’ is somewhat obscure - an English dictionary of 1725 defines the slang term ‘Old Roger’ as being synonymous with The Devil and a development from the term ‘rogue’. Early French buccaneers operating from Tortuga and similar bases are said to have referred to their blood-red flag as the jolie rouge (meaning ‘pretty red’) and these words corrupted through mis-pronunciation by English buccaneers who joined ‘The Brethren of the Coast’ later. It is also given that roger was a corruption of the East Indies term rajah brought back by seamen and some pirates in the very early 17^th Century giving the hint that in having considerable autocratic power over the life and death of his subjects, the term rajah was considered to be the equivalent in those lands and waters as ‘tyrant’ : one rajah in particular was known to be a real tyrant : as his name was Ali Raja and he was also a pirate, it is suggested that through verbal exchanges by English seamen his name became ‘Ally Roger’ or ‘Olly Roger’ in being associated with The Devil as Ali Raja flew a ‘blood red flag’ on his ships on a permanent basis … and he meant it!

The ‘skull and crossbones’ is a Christian symbol drawn from Revelations in The Holy Bible and is meant to symbolise Resurrection rather than Death: an offer of rebirth rather than ceasing to exists!  This particular example is shown on an early 18th Century tombstone and gave rise to the popular local tradition promoted for some years now in guided tours that a pirate is buried beneath it … Authors Collection

In the 17^th Century, a red pennant was commonly hoisted by the ‘senior’ ship in a fleet or the ship upon which sailed the fleet commander as a mark that in signalling that ship had ‘priority’ in transmitting orders and manoeuvring and could be another reason why pirates flew the ‘red flag’ by following this sea-faring tradition and declaring that their ship had total control. The ‘skull and crossbones’ motif was worn as a badge by elements belonging to the European military before and after the period in question (it is still the ‘Death or Glory’ cap-badge worn by the Queens Royal Lancers Regiment in the British Army).

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(well we couldn't miss out our own could we!)