History of the Jolly Roger

[Morgan La Scylla]

Legends of the Jolly Roger

One legend has it that the Jolly Roger obtained its appellation from the

French name for the red flag, the "Jolie Rouge." And so it may be, for

the flag was first used by a French order of militant monks known as the

"Poor Soldiers of Christ and the Temple of Solomon" - commonly known

as the Knights Templar.

The Templars, were pious men. They gave up all their worldly

possessions when they entered the Order, only carrying money on

special occasions when they traveled alone, turning over whatever

money that remained upon reaching their destination. They were

ferocious warriors; pitching themselves into the midst of their enemies,

astride charging warhorses, against incredible odds. Contemporaries had

this to say of Templars:

The Templars are most excellent soldiers. They wear white

mantles with a red cross, and when they go to war a

standard of two colors called balzaus is borne before them.

They go in silence. Their first attack is the most terrible. In

going, they are the first. In returning, the last. They await

the orders of their Master. When they think fit to make war

and the trumpet has sounded, they sing in chorus the Psalm

of David, "Not unto us, O Lord" kneeling on the blood and

necks of the enemy, unless they have forced the troops of

the enemy to retire altogether, or utterly broken them to

pieces. Should any of them for any reason turn his back to

the enemy, or come forth alive [from a defeat], or bear

arms against the Christians, he is severely punished; the

white mantle with the red cross, which is the sign of his

knighthood, is taken away with ignominy, he is cast from

the society of brethren, and eats his food on the floor

without a napkin for the space of one year. If the dogs

molest him, he does not dare to drive them away. But at

the end of the year, if the Master and brethren think his

penance to have been sufficient, they restore him the belt

of his former knighthood. These Templars live under a strict

religious rule, obeying humbly, having no private property,

eating sparingly, dressing meanly, and dwelling in tents.1

"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

"in turn lions of war and lambs at the hearth; rough knights

on the battlefield, pious monks in the chapel; formidable to

the enemies of Christ, gentleness itself towards His friends."

-Jacques de Vitry

Being men of principle; their rules of conduct were strict. They were

willing to die for their beliefs, and so were 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 entering the field. Their Rule of Order stated that breaking rank was worthy of losing ones habit. They neither asked nor gave quarter; the 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.

Templars were not to succumb to the temptation of thinking that they

killed in a spirit of hate and fury, nor that they seized booty in a spirit of

greed. For the Templars did not hate men, but men's wrongdoing.

They were dedicated to the protection of travelers and pilgrims of all

religions, though they themselves were Christians, in fact many Templars were of Palestinian birth, spoke perfect Arabic, and were familiar with every religious sect, cult, and magical doctrine, including that of the Islamic Assassins. The Grand Master Philip of Nablus (1167 A.D.) was a Syrian.2 They were great statesmen, politically adept economic traders, and they were allied with the great sailor-fraternity that had created a worldwide trading empire in Phoenician times. They became immensely powerful - had the largest fleet and the most successful banking system in Europe. But they could not sustain their grip on the Holy Land. Their losses3 were too great, and they were eventually driven off the Levant by Saladin, their Moslem adversary, in 1291. They continued to fight for their cause in the only manner they could - on the high seas.

The best known Templar pirate ship was the Falcon, "the greatest that

had been built at that time."4 She was in the harbor when the fortress

of Acre fell "and rescued many 'ladies and damsels and great treasure

and many important people'4 by evacuating them to 'Atlit."

After the orderly navel evacuation of 'Atlit, the Templars retreated to

their Mediterranean island bases on Cyprus, Rhodes and Sicily. Until their dissolution, they, together with the Order of St. John, continued as the foremost maritime powers in the Mediterranean, continuing to effectively wage war on Moslem shipping.

The Templars were still very powerful but in the eyes of European

monarchs and the Church, the Templars raison d'tre had ceased with the

loss of the Holy Lands. Jealousy and covetousness reigned. 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 13th 1307 - and the reason for which Friday

the 13th has become known as an unlucky day - King Phillip IV together

with Avignonese Pope Clement V, ruthlessly suppressed the Order

throughout Europe, with false accusations, arrests, torture and

executions. (Timeline) Though they were offered communted sentences

and comfortable lives if they would renounce their Order and plead guilty to the charges, for some mysterious reason, they preferred to remain true to their principles and received their punishment.

A large number of Templars escaped that day to an uncertain future,

and found refuge abroad. 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 down to this day.

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 as well as Europe, but still

formidable at sea, the refugee Templars found sanctuary in Scotland,

where Templar graves bear witness to them having lived and died there

in the fourteenth century. King Robert the Bruce had no interest in

persecuting the Order, in spite of a papal bull ordering him to do

precisely that. To the contrary, he took advantage of their fugitive

status, offering them asylum in return for their help in his war for

independence against King Edward II of England. Templars have been

suggested as the source of mounted soldiers who assisted Robert the

Bruce's Scots Guard at the battle of Bannockburn, as the Scots did not

have a mounted force.

As the Scots Guard continued through the years, two of the prominent

families involved in its history were the Sinclairs and the Stuarts. Both

families trace their lineage back to members of the Knights Templar, as

well as to prominent figures of the New Testament. Hugues de Payns

the first Grand Master of the Templars was married to a Sinclair.

There is also evidence that the Templar fleet traveled to North America

in 1398 (almost 100 years before Columbus) with the Sinclairs, and

settled there at least temporarily. Connections are made between the

tower ruins along the eastern coast of the United States, objects

discovered in the Oak Island "Money Pit", and the Templar Order.

The Sinclairs (or Saint-Clairs) castle near Edinburgh, was situated next

to Rosslyn chapel, which was constructed by the Sinclairs according to

the floorplan of Solomon's original temple. Engraved in the masonry

around the chapel are maize and aloe plants, which grew only in North

America.

Throughout Scotland, as well as within Rosslyn Chapel, there are

carvings and tombstones dating back to the 15th, 16th, and 17th

century using combinations of Templar imagery (skull and crossbones,

Templar swords, Templar crosses) and Masonic symbols (compass and

square).

The Stuart royal house became one of Freemasonry's biggest supporters during their reign of Scotland and England.

Some also suggest that the rituals used in modern Freemasonry have

their origins in the ancient texts discovered by the Templars in the ruins

of Solomon's Temple while excavating to build their stables. Recent

archaeological digs in the area have supported this theory by finding

serveral Templar artifacts buried beneath the temple. In the 1950's, a

scroll made entirely of copper was discovered in the caves near Qumran.

When translated with the other "Dead Sea Scrolls", this "Copper Scroll",

as it has become known, was identified as a treasure map listing various

precious metals, religious artifacts, and writings supposedly buried

beneath the temple in Jerusalem.

By the 17th and 18th centuries, the skull and crossbones was a symbol

with a powerful reputation but identified with no official organization.

The Templars had long since gone underground and evolved into other

organizations. The symbol was usurped and came to be associated with

the pirates of which we are more familiar. They changed the flag to suit

their needs replacing the crossbones with swords, adding hourglasses or

other symbols.

1. Anonymous Pilgrim V.2, tr. A. Stewart, Anonymous Pilgrims, I-VII

(11th and 12th centuries), Palestine Pilgrims' Text Society 6,

London, 1894 p 29-30.

2. A History of Secret Societies, Arkon Daraul, 1962, Citadel Press,

NY

3. At Harim in 1164 they had sixty dead from a contingent of

sixty-seven; in the space of a little over two months in 1187 they

lost 290 knights at the Springs of Cresson and at Hattin; in 1237,

while besieging Darbsak, the Templars of Baghras were heavily

defeated by Aleppan troops, leaving them with only twenty

survivors from a force of 120 knights; at La Forbie, in October

1244, they emerged with only thirty-three knights from the 300

they had contributed to the army; less than six years later, at

Mansurah, the Grand Master told Joinville that 280 of his knights

had been killed. It is natural to see such losses in human terms,

but at the same time it should not be forgotten that each of these

knights represented a large financial investment. In 1267 the cost

of maintaining a knight for the defence of Acre for a year was

ninety livres tournois. As a good estimate of the average annual

income of the French monarcy at the time of Louis IX's first

crusade is approximately 250,000 livres tournois, this means that

even if each knight killed at La Forbie represents only a year's

investment of Templar resources, the total loss was still little short

of a ninth of the annual Capetian income. - Barber, Malcolm, "The

New Knighthood", p232

4. Ramon Muntaner, Cronica Catalana, p. 368-9, also the Chronicle of

Muntaner tr Goodenough p466-9.

5. Principle - guiding sense of the requirements and obligations of

right conduct: a man of principle.

Paraphrasing the crusade historian William of Tyre, "Accepting that

'mistakes tend to creep into lengthy communications' [Prov 10:19], we

invite our reader to correct errors in the spirit of kindness." - CC LXIII,

p 101.

[Morgan La Scylla]

Jolly Roger Symbols Explained

The Jolly Roger, Old Roger, or just plain Skull and Crossbones is the definitive symbol of the pyrate. Although no one knows for certain, it is believed that the name derives from joli rouge, which means "Pretty Red" in French. This was taken to describe the blood red flags flown by particularly harsh pyrates. No matter where the name came from, the essential use of this banner was to strike fear into the hearts of the crew under pyrate attack. While pyrates often flew "false colours" of any given country, inevitably they used "truer" colours to communicate and threaten potential victims.

Around 1700 the first such flag was flown by Emmanuel Wynne as he plundered the Caribbean. In general, a white flag was flown when pyrates were in chase of a potential victim. In some cases the victim would "strike his colours", or take down the king's flag and submit to the bandits. If the victims refused, the black and white flag was raised to indicate the intentions of the pyrates.

In the event that a ship was particularly evasive, or a pyrate was particularly brutal, the red flag was raised to indicate that no quarter would be given once the ship was captured. In short no lives would be spared. The flags contained symbols designed to indicate a certain message.

Of course, the skull was a sign of death in general, but a skeleton, often with horns, was to indicate a tormented death. On the otherhand, a dart or spear was used to indicate a violent death in contrast to the bleeding heart denoting a slow and painful death. A raised fist or hand clutching a dagger or cutlass was to indicate a general willingness to kill and the hourglass gave a threat that time was running out or that capture was inevitable.

Curiously, Blackbeard managed to incorporate practically every one of these main symbols into his flag. Jack Rackham (Calico Jack) used a graceful set of crossed swords in place of bones to boast ironically of his willingness to fight. Similarly, Thomas Tew took the image of the sword before that of death. In his flag, no symbol of death is present, but the message is no less clear regarding the fate of any who opposed his advance. Sir Thomas Tew seemed to think it more polite to suggest violence without that nasty death image. These images were, of course,

interpretive, but well known in the golden age of pyracy. A flag could be a simple variation like Henry Every's (page top) skull at a profile, or it could be all inclusive like Stede Bonnet's rather bland jumble of images. As was the case often, a flag could be altered or customized to fit a particular need. In the case of Bartholomew Roberts (Black Bart) his "principle" colours showed him toasting death with an ambiguous glass of drink or an hourglass (pun intended for sure!). After a long hard time of pyratin' Black Bart came to hate the islands of Barbados and Martinique. To show his vendetta he crafted another flag showing him astride two skulls and the letters "ABH" and "AMH". The letters were to indicate "A Barbadian's Head" and "A Martinician's Head". While it is unclear if Bart ever got his Barbadian, in 1720 he hung the governor of Martinique from his yardarm.

[Morgan La Scylla]

Pirate Flags

For more than two centuries a black flag with a white skull and crossbones (Jolly Roger) has been the symbol for pirates throught-out the western world. In popular fiction all pirates flew the jolly roger. However, this special flag was used only by British and British-American pirates from about 1700 to 1725. Other pirates attacked either under their own ruler's flag or under the flag of the official issuing their privateering commission. By flying a national flag, pirates made a symbolic statement (often false) that the attack was legal under that country's laws. Some nations sponsored piracy and lived off pirate booty, including Barbary states, the Knights of Malta, and 17th-century England. In law, corsairs operating from one of these havens had to fly its flag. This showed that the raiders recognized and paid taxes to the ruler's law courts.

The pirate flag, or Jolly Roger as it was also known was designed to strike fear into victims and encourage a hasty surrender. It probably traces its origins to the plain black flag that a ship would fly to warn another to surrender at once, or else it would be replaced by the red flag, or Jolie Rouge in French, meaning no quarter given (no mercy would be given to the crew). Many showed skulls and crossbones or skeletons, meant to warn of death if the victim did not surrender. Many of these symbols were probably borrowed from gravestones of the time. A few of the flags also contain an hour glass, meaning that time is running out for the victim to surrender peacefully. The pirates wanted to project fearlessness in the face of death, and some flags pictured the captain toasting, dancing with, or literally conquering the skeletal dead. Hearts to were often pierced to symbolize "no mercy".

While they were hunting, many pirates either flew no flag or used one that was meant to fool their intended victim. Normally their battle flag was raised only when they were close enough to attack. On one occasion the famous pirate Bartholomew Roberts was able to deceive the shipping off the island of Martinique by flying Dutch flags and making signals normally used by Dutch ships arriving from the Guinea coast of Africa with black slaves. This ruse enabled him to capture fourteen French sloops which came out to meet him with large sums of money on board for trading in slaves. Naval warships also used these tricks. In 1815 American ships thus trapped the 'Hamidou Reis' by flying the British flag. Some pirates, such as Edward Teach, better known as Blackbeard, kept a collection of flags on board and simply raised whatever was most convenient in any given situation.

[Morgan La Scylla]

More Infamous Flags

[Black Syren]

I was doing an image search on these and came across this article. Thought to post it for others to read.

Jolly Roger History

[Fox]

Puts spoil-sport hat on yet again

Alas, the supposed link between Templars and pirates is fanciful and speculative at best. Despite many claims that the Templars used the skull and cross-bones as a flag there has yet to be produced one single piece of evidence to support them.

Although David Hatcher Childress in his book "Pirates and the Lost Templar Fleet" tries to make a case for the "jolly roger" originating with the Templars his theory is based on well... nothing. There's no real reason at all to suppose that the famous pirate flag was any older than the late 17th century. As a motif the skull and cross bones is certainly older, but there is no continuity between say, medieval gravestones and pirate flags other than an obvious symbol of mortality.

What was your original line of enquiry? I'm currently involved in seriously researching pirate flags, I may be able to help.

[Black Syren]

Actually I was studying the diffrent designs of the Jolly Roger to make my own. I have one that was created for me..But I wnated to make it a little diffrent and enlarge it to pain and put on a purse. I stumbled across that and found it intresting enough to post.

[Fox]

These are genuine historical jolly rogers which contain devices other than the normal ones found on the web, maybe they might give you some ideas.

[Tempest Fitzgerald]

It is to my understanding in regard to research that I have done in the past, that the original "colors" coming into play were that of a solid red field with no adornment and have noted reference to a solid black field, as well. These used well before the adorned flags that most are familiar with. (The red signaling "no quarter", the black signaling "death".) I have seen reference to the red flag being called the Joli Rouge, a French term meaning "pretty red". There are certain schools of thought that theorize the term, "Jolly Roger" is an evolution from the french term in origin.

[Fox]

It is certainly true that plain red and black flags pre-date "jolly rogers", Drake for example is known to have flown black flags at the seige of Cartagena in 1585, and at least one ship in the English fleet of 1588 had aboard a "bluddey flagge". What isn't certain is the continuity between these early flags and later pirate flags. The history of the red flag can be traced through most of the 17th century but the case for black flags is weaker. For example, although there are several records of Caribbean buccaneers flying red flags I have not yet found one flying a black flag.

The question of the meanings of flags is an interesting one. George Roberts, who was captured by Spriggs, certainly says that the black flag is one of intimidation and the red flag was a signal of no quarter. On the other hand, at least one other source suggests that actually a black flag was considered more terrifying. On the whole though, most sources back up the notion that black flags were used for identification and intimidation, and that red meant no quarter.

As to the origin of the phrase "jolly roger", the joli rouge theory is perhaps the most likely on the face of it, but the best supported by the evidence is that the term comes from "Old Roger", meaning the devil. The term "Old Roger" to describe a pirate flag predates "jolly roger" by about 20 years, and if indeed "Old Roger" is the older term then it cannot have derived from "joli rouge", or the somewhat ridiculous idea of "Ali Rajah".

[Tempest Fitzgerald]

Very Interesting, Foxe! You have enlightened me further and one can never have to much familiarity with said subjects. Thank you for your studious pursuits.

[Fox]

Oops, my bad. Richard Hawkins was captured by Spriggs and described his flags, not George Roberts. Roberts described one of Low's flags...

You're welcome Tempest.

[Jolly Roger the Red]

Pirates have many nations of origin and cover a vast period of time including the 21st century. I think you may find during your research many conflicting stories. I suggest that more then one source for the term "Jolly Roger" is likely to be the truth since languages get rearranged as time passes. I know of an island named "Bois Blanc" which is french for White Wood. The current residents of Bois Blanc pronounce it "Boblo" You may find that a strange way of pronouncing it but they think nothing of it at all. It has been that way so long they take offence when it is pronounced properly. Just a thought!

Now I be Jolly Roger the Red so I be leanin heavy towards the "No Quarter" Flag and I be called "Old" many a time so if'n ye be thinkin me the devil; Thinks what yer will says I. What say You?

[Rumba Rue]

I too question the Jolly Roger being associated with the Knights of the Templar. It's the first I've heard of it.

I'd like to know where this source(s) of information comes from and what true history there is to back it up.

[Fox]

Weeeell, whenever I've managed to ask someone who espouses the Templar/Jolly Roger link what the actual evidence is the answer is almost always the same. An assurance that the evidence exists, but nobody seems to know (or is prepared to say at any rate) what or where this evidence is. You believe it? Nope, me neither.

Of course, since the Jolly Roger connection is one of the corner stones of the whole Pirate-Templar link if we discount it then we might have to admit that the whole attractive Templar-Pirate "history" is just a load of sham and hogwash, and that would be very sad.

Here's to decent historical research winning the day.

[Cire]

But Foxe! The pirate-Templar link is real! It is as true as the pirate-ninja conflict, and we all know that is no lie.

[Fox]

I will grant, quite happily, that the Pirate-Templar link is every bit as real as the pirate-ninja conflict.

[Fox]

Ok, so I decided it was about time I read "Pirates and the Lost Templar Fleet" by David Hatcher Childress. I've been slating his theories for long enough based on a few excerpts I've read and other people's summing up of his work, but due to the relative difficulty of finding a copy over on this side of the pond I'd not read it right through until now.

I tried so hard to keep and open mind, I really did, honest! It's just so hard when the "facts" being given are so completely self-contradictory. A child of ten could break down his theories based only on what he's written himself - but that's getting off the point.

The point is that when one asks people who espouse the Templar-Jolly Roger connection what the evidence is, if they are able to provide any at all it's a recommendation of this "book". About half way through the third chapter Childress tells us that Templars flew the skull and cross bones. No evidence, no reasons, no nice period pictures, just a statement that we are required to believe. Since one of my main purposes in reading this book was to find out the source of that statement I naturally found it a little frustrating. And it got more frustrating every time he repeated the statement without qualifying it.

Finally, near the end of the book he tells us what his source for the statement that Templars flew the Jolly Roger is: unequivocally he states that it's "Under the Black Flag" by David Cordingly. Now, I challenge you pirate people to find a mention of Templars flying the jolly roger in "Under the Black Flag". I've checked and can't find it. Didn't even find a mention of the Templars at all in fact.

What Childress has done is made up a "fact" from his own imagination and in order to give it more credibility had falsely attributed it to a respected historian of the type he spends half the book railing against.

There we go folks. Even the most ardent exponent of the Templar-Pirate connection is reduced to plainly and obviously making stuff up.

[MadMike]

Foxe,

And now my favorite topic of discussion... what materials were used for these flags?

We know that some pirates used silk, but were the devices painted on or sewn on?

Many 17th and early 18th century flags were painted, but we have one 1840's pirate flag which was sewn on (with what appears to be a partially painted skull and crossbones highlighting certain features).

I painted a black cotton fabric 3'x5' flag with Edward Englands motif, came out pretty well.

One should imagine that it wouldn't take too long for a pirate crew to hand sew devices on their flag. Then again, it's just as easy to paint it (better than using a dirty tarpaulin!).

Yours, &c.

Mike

[Master Sully]

I have read theories on how the skull and crossbones became a symbol on the Jolly Roger. The Vatican produced many Crusifixes with a symbol of the skull and crossbones under Christ's feet , to represent his triumph over death. Many Catholics used the same symbol on headstones and other epitaphs. Many English, Irish,and Scottish captain's would use a skull and crossbones marking next to a deceased sailor's name in their logs. The sailors recognized the symbol as death. As an intimidation factor, the sailors ( turned pirates ) would fly this symbol as they shadowed their prey for some time. The sailors of the other ship would feel as if Death was following them and scare the $#*! out of them.

[Pirate Petee]

I've never heard of this. What is this link between knights and pirates? Who are they?

[Fox]

The Knights Templar were a religious order of crusading knights from the 12th-14th centuries who had absolutely nothing whatsoever to do with pirates of the 17th and 18th centuries and who didn't fly a skull and cross-bones from their ships.

Master Studley has it just about right in my opinion, except I would say that the use of the skull and cross bones on gravestones was not an exclusively Catholic practice by any means - it was a really common symbol signifying mortality, hence its use in ships' logs and pirate flags.

Mike, although there are several records of the materials used to make flags by GAoP era pirates I can only think of one description of the actual method of applying the design specifically described. Since there are no extant pirate flags from that period we are entirely dependent on literary sources for this information.

At the trial of Roger Hews and other pirates in Scotland one of the witnesses who had been a member of Cocklyn's crew deposed that cocklyn's flags were painted with their devices. Of course, it's quite likely that they were sometimes sewn, but I don't know of any period source to support that for certain.

[MadMike]

Foxe,

I looked through a flag book recently and was amazed at the 17th and 18 century hand painted unit insignia, coats of arms, etc., on British and French flags, simply amazing. I have a book on the War of 1812 by Rene Chartrand which also shows hand painted ensigns.

It's really unfortunate we don't have a Caribbean GAoP flag.

I used oil based paint on my flag, hand painting it in. The design shows through the other side of the cloth so working it is no problem (just time consuming). Used two coats, flies great in a breeze.

Just located some black silk, so my next expenditure will be to hand make a Bartholomew Roberts flag.

Yours, &c.

Mike

[Fox]

The last big flag I made was oil based paint on black cotton and it worked much the same. Outlined the design in chalk, painted it in, then turned the flag over and painted the other side where it had come through.

If you're going for historical accuracy with a Bart Roberts flag then this one is authentic

But this one is probably a later invention (it's an 18th century invention, but there's no good evidence that Roberts flew it)

However, Bart Roberts is also known to have flown these flags if you're looking specifically for one of his.

- -

As well as an English red ensign, RN pennant, plain black pennant and Dutch pennant.

He may also have flown these two.

-

[Tall Paul]

I think that if the red flag represented "No Quarter Given", There is a degree of logic to it being superseded by the black flag.

I read somewhere that a common practice was to fly the black flag whilst attacking, but after a period of time had passed, if the pirates had the advantage, the black flag was struck, and replaced with the red flag indicating that it was too late for surrender, as no quarter was to be given. Presumably the intention of this practice was to persuade the attacked crew that once the battle had turned against them, they should surrender before the red flag was raised.

If the pirates attacked flying the red flag, indicating that no quarter would be given. There is no benefit in surrendering. Although the message of attacking flying the red flag is the more terrifying, there would be no benefit to the attacked in surrendering. It would be in a pirates best interest to persuade their victims to give up without a fight. (As sometimes happened so I believe.) So experience would have shown the benefit of flying the Black flag instead of the red.

As for the skull and cross bones, its use was wide spread during the 17th and 18th It appears on gravestones funeral invites and pious people sometimes carried small fobs or other jewellery in the form of a skull or even a skeleton as a reminder of their own mortality. (incidentally, I think that this is why it is unlikely that a pirate would have be-decked himself with skull jewellery, he had probably long since come to terms with his own mortality, and even if he hadn't, he would be unlikely to be openly wearing items that were associated with a fear of death.) Remember that during the second half of the 17th century, the black death was within living memory, and epidemics were still common. Pirates simply exploited their intended victims familiarity with these symbols, and used them to install fear.

likewise, during this time period, Death was represented not as the scythe carrying be-robed figure that we think of today, but by an emaciated, skeletal figure carrying a lance and an hour glass. another common figure on pirate flags.