He scanned the water. Aha. There. If he squinted, he could just make out the ship’s flag. Black and white. A cricket bat -- no, two. No, maybe swords. Two crossed swords and a giant…apple…no. A skull. A skull and…He dropped the spyglass.A skull and crossbones. Pirates.
The flag flown to identify a particular ship usually identified its country of origin. Since pirates were under threat of capture and execution, they were outlaws without a homeland.
Some pirates did maintain an allegiance to their native countries. For example, English pirate Benjamin Hornigold refused to attack any ship flying
British colors .
But it was much more common for pirates to consider themselves wanted men (or wanted women) -- which, indeed, they were. Although there’s the occasional story of a pirate who retired or gave up the sweet
trade, the reality is that most pirates died in battle or on the gallows.
Given that there really was no safe ‘home’ nation, they considered their own crews, the deck beneath their feet, the company of other pirates, to be their homeland.
There were
sovereign nations ruled by kings and queens, but on the sea, pirates bowed to no authority but their own. Hence, they were, in the collective, a nation of their own. And a nation must have a flag.
Pirates lived with the constant threat of death -- they might be injured or killed in a fight to take a ship, they might die of an infected wound or contagious disease spread in close quarters, they might be captured and strung up.
So, rather than fear death, pirates grudgingly acknowledged this ever-constant, unwanted companion, with signs and symbols that acknowledged that the dark reaper was the shadowy captain of any pirate vessel that ever sailed.
Common emblems or symbols found on pirate flags, then, were the deadly tools of their trade, like spears or
cutlasses and the marks of death victorious --skeletons, bones and blood, or that badge of piracy immediately
recognizable even to contemporary audiences, the skull and crossbones.
The background of flags were often black; this particular color choice likely originated from a grim maritime tradition -- black flags were flown on plague ships, as a warning that to board could be to risk a terrible death.
The tradition of hoisting a black flag -- or, in later days, a checkered yellow and black flag for improved visibility -- to warn other seafarers away from a plague ship, was still being used in 1896, as noted in
this entry from the
Encyclopædia Britannica, Vol. 22:
The existing British regulations are those of 9th November 1896;
they apply to yellow fever, plague and cholera. A stricken ship within
three miles of the shore must fly at the main a yellow and black flag
borne quarterly from sunrise to sunset.
Flags could identify a friendly ship, that of the same nation, or it might be used to signal a requested meeting alongside. Flags were used to communicate intent or origin in the
Golden Age of Piracy, and they’re even used today, via the
International Code of Signals (ICS), to communicate quickly in a visual form.
What pirate flags signified was trouble ahead for whoever was unlucky enough to see one…
Hoisting the skull and crossbones, or any flag with a similar motif, could be used as a visual threat to convince the captain of a pursued ship to surrender. Pirates weren’t bound by the traditional rules of engagement, and resistance might be met, not with capture and a ransom demand, but with death.
It was, in fact, better to take a ship with little or no resistance, otherwise pirate crews themselves faced the danger of death or serious injury in close, hand-to-hand combat. An easy capture also prevented damage to the ship being taken, and the treasures it held.
Of course, it was also easier to take a ship if the crew had no forewarning and couldn’t bolt. A common ruse was to fly the colors of a particular nation, especially the colors of the same nation as the targeted ship. When within hailing distance, the false colors were dropped and up went the black flag.
Hoisting the colors wasn’t something that could be taken on lightly, as just the possession of a flag could be enough to get a crew hanged for piracy, as noted in this paper by economics scholar (and pirate
aficionado) Peter T. Leeson:
Ships attacking under the death head's toothy grin were considered
criminal and could be prosecuted as pirates. Since pirates were
criminals anyway, for them, flying the Jolly Roger was costless. If
they were captured and found guilty, the penalty they faced was the
same whether they used the Jolly Roger in taking merchant ships or not
-- the hangman's noose...
For legitimate ships, however, things were different. To retain at
least a veneer of legitimacy, privateers and Spanish coast guard ships
could not sail under pirate colors. If they did, they could be hunted
Pirates flew the Jolly Roger for all these pragmatic reasons -- but also just because they really had nothing to lose. Pirates already defied kings, queens, governors and the seafaring crews of nearly all nations just by virtue of their profession, and lived every day under the threat of death. Perhaps it was a grim pleasure to see a jolly death’s head grinning back at them.
In contemporary popular culture, the typical skull and crossbones pirate flag is nicknamed the Jolly Roger -- but the term was actually in effect as far back as 1724.
The term ‘Jolly Roger’ or ‘Jack’ to denote a pirate flag is mentioned in
A General History of the Pyrates
(1724), by
Captain Charles Johnson ; the author’s name is generally
acknowledged to be pseudonymous, and authorship usually attributed to
Daniel Defoe, who wrote the now-classicadventure novel,
Robinson Crusoe.
The term ‘Jolly Roger’ is possibly an English variation of the French,
jolie rouge, or pretty red. English privateers (privateers were effectively something like legalized pirates, given royal or legal
sanction to attack the ships of other nations) were to fly the Red Jack, by
Royal Proclamation in 1694.
Disbanded privateers might have carried on under the same flag, although a red flag flashing from the mast of a pirate ship usually took on a more sinister meaning. Red flags usually denoted that any fight would be to the death, with no
quarter given or expected.
Another possible explanation for the origin of the term, ‘Jolly Roger,’ was the combination of ‘Old Roger’ (a 17th century nickname for the devil), and the fact that the skinless skulls seem to be perpetually grinning at the beholder -- thus, a grim kind of jolly smile.
It’s really anyone’s guess where the term Jolly Roger initially came from; as with most slang, it’s nearly impossible to pinpoint the exact origin of the term. In any case, though, it was already being used in
1724.
A General History of the Pyrates specifically mentions the use of various designs and uses the names Jolly Roger or Jack as generic terms for pirate flags.
As noted, elements in pirate flags served as a warning to others and so the skull and crossbones motif was a common theme, signifying death. Actually,
the image is even used today, on warning labels for poison or other toxic materials.
A combination of yellow and black, as used in later maritime tradition to signal infectious disease onboard, is also used in messages warning of a biohazard, as shown in the image above.
And now, here’s a gallery of pirate flags, and the pirates who reportedly flew them from their masts and
ensign staffs.
Black Bart: Bartholomew ‘Black Bart’ Roberts was one of the most successful pirates alive during the
Golden Age of Piracy , capturing over 470 vessels.
He treated prisoners relatively humanely and his crew was so loyal to him that when he was killed in a sea battle with English pirate hunters, they threw his body overboard rather than let his corpse be seized for a reward.
His fatalistic but chipper philosophy, given in
The Pirates Own Book, by
Charles Ellms , was, ‘A merry
life and a short one, shall be my motto!’
His flag in particular is mentioned in
A General History of the Pyrates:
Roberts was so enraged at the attempts that had been made (to capture him) that he ordered a new Jack to be made, which they ever after hoisted, and under them the letters A.B.H. and A.M.H, signifying a Barbadian's and a Martinican's head. (
Read excerpt, pg. 221)
The reason for Black Bart’s enduring ire is explained in the book
Black Barty, by archaeologist
Aubrey Burl :
The inhabitants of Barbados equipped two well-armed ships, the Summerset and the Philipa, to try to put an end to the pirate menace. On 26 February, they encountered the two pirate sloops (Bart’s ship, the Fortune, and French pirate Montigny la Palisse’s ship, the Sea King). The Sea King quickly fled, and after sustaining considerable damage, the Fortune broke off the engagement and was able to escape.
Roberts headed for Dominica to repair the sloop, with twenty of his crew dying of their wounds on the voyage. There were also two sloops from Martinique out searching for the pirates, and Roberts swore
vengeance against the inhabitants of Barbados and Martinique. He had a new flag made with a drawing of himself standing upon two skulls, one labeled ABH (A Barbadian's Head) and the other AMH (A Martiniquan's Head).
Edward ‘Ned’ Low : An English pirate infamous for his extreme cruelty. Born into poverty in Westminster, London, into a reputed family of thieves. Moved to Boston, Massachusetts as a young man. His wife died in childbirth in late 1719. Two years later, he became a pirate.
As recounted in <
The Pirates Own Book (1837) by Charles Ellms,when Low decided to go to the devil, he didn’t do it by halves:
Of all the piratical crews belonging to the English nation, none
ever equaled Low in barbarity. Their mirth and their anger had the
same effect. They murdered a man from good humor, as well as from
anger and passion…
One day, Low, having captured Captain Graves, a Virginia man, took a
bowl of punch in his hand, and said, ‘Captain, here's half this to
you.’ The poor gentleman was too much touched with his misfortunes to
be in a humor for drinking, he therefore modestly excused himself.
Upon this Low cocked and presented a pistol in the one hand, and his
bowl in the other, saying, ‘Either take the one or the other.’
Shown above: Pirate Edward Low offers an unhappy guest on his ship a bowl or a bullet.
Low next captured a vessel called the
Merry Christmas, mounted her with thirty-four guns, went on board her himself, assumed the title of admiral, and hoisted the black flag.
His next prize was a brigantine half manned with Portuguese, and half with English. The former he hanged, and the latter he thrust into their boat and dismissed, while he set fire to the vessel.
The success of Low was unequalled, as well as his cruelty...All wickedness comes to an end and Low's crew at last rose against him and he was thrown into a boat without provisions and abandoned to his fate. This was because Low murdered the
quartermaster.
His flag is described in an excerpt from
A General History of the
Pyrates:
The latter end of July (1723), Low took a large ship, called the
Merry Christmas, and fitted her for a pirate, cut several ports
in her, and mounted her with 34 guns. Low goes aboard of this ship,
assumes the title of admiral, and hoists a black flag, with the figure
of death in red, at the main-topmast head, and takes another voyage to
the Western Islands, where he arrived at the beginning of
September.
Emanuel Wynn: His flag, featuring a skull with an hourglass below to let his prey know that their time had run out, was one of the first mentioned in maritime
reports or elsewhere, in histories about pirates.
One of the earliest references to this flag is made by Captain John Cranby, a pirate hunter, who reported an encounter with Wynn in 1700. This is reported in the book,
The Pirate Wars, by economics history scholar and maritime researcher
Peter Earle :
and tenacious pirate, but his chief claim to fame in pirate annals is
his flag , which was described by Cranby
as 'a sable ensign with crossbones, a death's head and an hourglass,'
the very first reference to this classic symbol of piracy.</i> (The
The availability of historical materials on Emanuel Wynn is minimal, so the source of information for this brief bio is the report, excerpted above, by maritime researcher Peter Earle.
Richard Worley: An 18th century English pirate whose preferred territory was the Caribbean Sea and the east coast of the
American colonies (the American colonies later unified to become the
United States of America).
Worley was one of the earliest pirates to fly the skull and crossbones. He and his crew agreed upon a set of articles, which included a provision on the subject of pirate hunters and possible capture -- Worley and his crew vowed to fight to the death rather than surrender.
Worley is mentioned, and his flag described, in an excerpt from
A General History of the Pyrates:
Worley had by this time increased his company to about five and
twenty (25) men, had six guns mounted, and small arms as many as were
necessary for them, and seem'd to be in a good, thriving sort of a
way.
He made a black ensign, with a white death's head in the middle of it,
and other colors suitable to it. They had all signed articles, and
bound themselves under a solemn oath, to take no quarters, but to
stand by one another to the last man, which was rashly
As the account doesn’t include mention of a set of crossbones, history buff
Ed Foxe puts forward an alternate image that he thinks could be a more accurate representation of
Worley’s ensign :
Shown above: An alternate representation of the flag attributed to pirate Richard Worley. The reasons for this alternate pick are given
here.
You can find a gallery of pirate flags
here and browse some historical notes about
which pirate flags are likely to be real, and which might be later fabrications,
here.
Feel free to join us on
Random Magic Tour: Pirates! for lots of other interesting features about pirates -- pirate gear, pirate grub, and pirate queens.