The Jolly Roger 

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The “Jolly Roger” is the term applied to any of the flags flown bearing versions of a skull and crossed bones. Below is some background on the possible origins of the term. Note that the discussion of Scotland and the use of skull and crossed bones imagery dates back well before the 1500's, into at least the middle ages.

One One theory is that the “Jolly Roger” obtained its appellation from the French name for the flag with a red cross, or a red flag, the "Jolie Rouge." And so it may be that the flag was first used by a French order of militant monks known as the "Poor Fellow-Soldiers of Christ and the Temple of Solomon" - commonly known as the Knights Templar. The Templars were pious men who gave up all their worldly possessions when they entered the Order. They had the reputation of being ferocious warriors; pitching themselves into the midst of their enemies, astride charging warhorses, against incredible odds. Historical accounts noted that contemporaries had this to say of Templars:

"The warriors are gentler than lambs and fiercer than lions, wedding the mildness of the monk with the valor of the knight, so that it is difficult to decide which to call them: men to adorn the Temple of Solomon with weapons instead of gems, with shields instead of crowns of gold, with saddles and bridles instead of candelabra: eager for victory -- not fame; for battle not for pomp; who abhor wasteful speech, unnecessary action, unmeasured laughter, gossip and chatter, as they despise all vain things: who, in spite of their being many, live in one house according to one rule, with one soul and one heart." -- St. Bernard of Clairvaux

Being men of principle, the rules of conduct for the Templars were strict and they were willing to die for their beliefs. This made them feared on the battlefield, and respected in life. Such was their reputation that, in battle, there were instances where the enemy would turn and run at the very sight of Templars taking to the battlefield.

One rule of their Order stated that breaking rank was worthy of losing ones “habit,” so they neither asked nor gave quarter. They were expected to fight until death stayed their sword arm. Retreat from an enemy would not be countenanced unless the odds were greater than three to one against them, and they were forbidden to ransom themselves if captured. They fought like men possessed, either prevailing in their cause, or suffering death under the banner of Gol'gotha, the place of the skull, where their Christ died.

They were also dedicated to the protection of travelers and pilgrims of all religions, and were considered great statesmen, politically adept, and economically sound traders. More importantly for the purposes of our discussion here, it is also believed that they were allied with the great sailing fraternity that created a worldwide trading empire in Phoenician times. Over time, the Templars became immensely powerful, and had the largest fleet and the most successful banking system in Europe. However, they suffered the fate of all such great and powerful dynasties when they could not sustain their grip on the Holy Land. Their losses were too great, and they were eventually driven off by Saladin, their Moslem adversary, in 1291.

The Templars retreated to Mediterranean island bases on Cyprus, Rhodes and Sicily. They, together with the Order of St. John, continued as the foremost maritime powers in the Mediterranean, effectively waging war on Moslem shipping. The Templars were still very powerful, but in the eyes of European monarchs and the Church, the Templars reign should have ended with the loss of the Holy Lands. Jealousy and covetousness reigned, and Phillip IV, who was deeply in dept to the Order, had seen their treasures stored in Paris and designed to make it his own. On Friday morning, October the 13th, 1307, King Phillip IV, together with Avignonese Pope Clement V, ruthlessly suppressed the Order throughout Europe with false accusations, arrests, torture and executions. This is believed to be the reason Friday the 13th has become known as an unlucky day.

On the eve of the arrests, the entire Templar fleet mysteriously vanished from the port of La Rochelle, carrying with it a vast fortune, the fate of which remains a mystery to this day. When they were driven out of Europe, a large number of Templars escaped that day to an uncertain future. Those that survived continued to fight for their cause in the only manner and place they could – aboard ships on the high seas.

Just as a terrorist to one is a freedom fighter to another, so it was with the Templars and their fleet. Wanted by the Pope and all the crowns of Europe, they came to be viewed, by the comfortable folks on the mainland, as “pirates.”

After being driven out of the Holy Land and Europe, many refugee Templars found sanctuary in Scotland. Templar graves bear witness to them having lived and died there in the fourteenth century. And, throughout Scotland and within Rosslyn Chapel, there are carvings and tombstones dating back to the 15th, 16th, and 17th centuries using combinations of Templar imagery (Templar swords, Templar crosses), Masonic symbols (compass and square), and the skull and crossed bones.

The “Templar theory” suggests that after the knights were driven out of Europe and the Holy Land, and members of their order were persecuted, they adopted the skull and crossed bones as an emblem of their fierce reputation, and because the shape of the crossed bones resembled the shape of their red cross.

By the 17th century the Templars had long since gone underground and devolved into other organizations, so the skull and crossbones was a symbol with a powerful reputation but identified with no official organization. The extension of the Templar theory is that since the Templar ships became known as pirates, the symbol was usurped and came to be associated with all pirates. Pirates then changed the symbol on the flag to suit their needs. They replaced the cross-bones with swords or guns to imply the threat of violence; added hourglasses to signify that time was running out; and sometimes changed the skull into the shape of a man or other symbol which they could use to particularly identify themselves. Pirates would then fly their “Jolly Roger” whenever they attacked a ship to use the imagery on their flag to strike fear in the hearts of the crew they were about to attack. The “Jolly Roger” showed that the pirate ship intended to take no quarter (meaning leave none alive).

However, one maritime historian, Mr. Ed Foxe, has made an in-depth study of pirate flags and contends that while the “Templar theory” is not a bad theory, quite attractive in fact, it does have one major flaw. There is no documentation to show that the skull and crossed bones were ever actually used as a Templar symbol. According to Mr. Foxe, the origin of the Templar theory seems to be a book called "Pirates and the Lost Templar Fleet," by David Hatcher Childress.
Mr. Foxe notes that while the skull and crossed bones certainly appear on some Templar graves, it also appears on hundreds and hundreds of other, non-Templar, graves from the medieval period to the 18th century. It was a symbol of mortality and death, but was never ever specifically associated with Templars. Nor did it ever fly from any ship known to be in the Templar fleet.
Whichever theory you adhere to, one thing is certain, when a ship approached and you saw a “Jolly Roger” run up its halyard, you knew it was going to be a very unlucky day! Shown below are “Jolly Rogers” known to have flown aboard pirate ships, and the person with whom they were primarily associated.

Bartholomew Roberts (2)
Bartholomew Roberts
Edward "Blackbeard" Teach
Christopher Condent
Christopher Moody
Edward England
Edward Lowe
Emanuel Wynne
Henry Every
Jack Rackham
Richard Worley
Stede Bonnet
Thomas Tew
Walter Kennedy
 

The “Jolly Roger” shown below is the one flown by Captain Thomas Maclaren of the Dauntless, but only when attacking a ship under Letter of Marque, of course. The skull with the bloody scarf, and the crossed bones, are intended to warn the crew of a ship being taken that the intentions of the Dauntless are serious, and that failing to “heave to” could be deadly. The outline of the red cross in the background is intended to imply that the crew of the Dauntless has the fierceness and conviction of the once feared Knights Templar, and the warning offered by the skull and cross-bones is not to be taken lightly.

So... Heave To, And Prepare To Be Boarded… Or ELSE!