Glen is a professional writer and illustrator from Cape Cod who writes on an array of subjects including science, history, music, and more.

The Golden Age of Piracy, a period spanning the mid 17th and early 18th centuries, was when high-seas piracy was at its peak. It was during this time that pirate flags began to bear symbols of violence and death—such as the skull and crossbones—designed to frighten and intimidate a pirate's intended victims. (Prior to the advent and popularization of the "Jolly Roger" we know today, pirates flew simple red or black flags devoid of design.)

Here's a look at the decorated pirate flags of that era, with explanations of their most common symbols and examples of flags used by some of the most famous pirates in history.

Though the term "Jolly Roger" has come to symbolize the ubiquitous skull-and-crossbones design, in the 1700s, it was used to describe any pirate flag (even if it sported no design at all).

History of Pirate Flags

The earliest pirate flags of that era actually bore no designs, but were flags of solid red or black. The origin of the red flag can be traced back to the English privateers of the late 1600s, who were required to fly red flags to distinguish their vessels from those of the Royal Navy. Many of these privateers later turned to piracy and continued to use the red flag.

Black Pirate Flags

Other pirates chose to fly a black flag. Black, of course, has long been associated with death, and black flags were often flown at the time by ships containing plague victims as a warning to stay away. By flying a black flag, a pirate was saying that his ship, too, was a "death ship".

Red "No Quarter" Flags

The red flag, when used by pirates, came to mean "no quarter given", meaning that no mercy would be shown and no life would be spared, while a black flag usually meant that those who surrendered without a fight would be allowed to live.

Where Did the Name "Jolly Roger" Come From?

There's no one answer to this oft-asked question, but there are a few good theories. Here are just a few:

It's a loose version of "Jolie Rouge" ("pretty red").

It's a play on "Old Roger"—another name for the devil.

It's a rough phonetic variant of "Ali Raja" ("King of the sea").

These are just three of the possible origins of the Jolly Roger moniker, but there are many more!

How They Were Used

A pirate vessel usually did not fly the pirate flag at all times. A vessel at sea can be seen from a long distance away, so pirates would usually fly the "friendly" colors of one nation or another, enabling them to approach another vessel without raising suspicion. Only when they were close to a vessel that they intended to take would they raise their own flag.

Pirates who raised a black flag were usually hoping to intimidate their prey into surrendering without a fight. Although pirates were usually excellent in combat (those who weren't didn't last long), they generally preferred to take a vessel without a battle. Fighting was risky and might damage the contents of the ship being taken—the pirate's booty.

Pirate Symbols and Their Meanings

Many pirates continued to fly plain black or red flags, but some captains began to embellish their flags with symbols representing violence, death, and even the devil himself. These objects were usually white, although red (representing blood or the devil) was sometimes used. Yellow was also used occasionally, most likely because it could easily be seen against a black or red background.

Symbol Meaning Skull, skeleton or bones Death Red skeleton A particularly violent and bloody death Skeleton with horns The devil Dripping blood A slow, painful death Weapons (swords, spears, daggers) Violence, a pirate's willingness to fight Hourglass (sometimes with wings) Time is running out or flying away, death is near Initials May refer to the captain, or to his enemies Raised glass A toast to death or to the devil Clothed figure Usually represented the pirate captain Naked figure A pirate's lack of shame

Why Did Pirate Have Flags on Their Ships?

Famous Pirates and Their Flags

The skull-and-crossbones design was used by pirates such as Edward England and "Black Sam" Belamy, but other designs have become associated with specific pirate captains. There are no surviving pirate flags from the 17th and 18th centuries, so many of these designs are based on eyewitness accounts. Some designs have become associated with certain captains over time, but not all of these have actually been confirmed as having been flown by the pirates in question.

Emanuel Wynn's flag is often credited as the first to sport the now-classic skull and crossbones. Public Domain via Wikimedia Commons

Emanuel Wynn

Among the earliest pirates to put a Jolly Roger on his flag—in fact, often credited as the first to do so—was the French pirate Emanuel Wynn. Eye-witnesses described a flag depicting a skull, crossed bones and an hourglass being flown on Wynn's vessel around the year 1700.

The meaning of the hourglass is disputed. It could either be interpreted as a message to the pirate's victims that their time was almost up, or that their only chance of survival was to surrender immediately.

Wynn was active in the Carolinas and the Caribbean, but not much else is known about him. In fact, the only written report about him comes from British Admiralty's Captain John Cranby of the HMS Poole and notes Wynn's escape.

Richard Worley's flag was one of the earliest versions of the Jolly Roger. Orem, CC BY-SA 3.0, via Wikimedia Commons

Richard Worley

Richard Worley, who spent a mere five months as a pirate before meeting his end, is better remembered for his design of the now universally recognized Jolly Roger flag—a skull and crossbones on a black background. Though he was not the first to fly a flag adorned with these symbols—an honor often attributed to Emmanuel Wynn—Worley's version is one of the most famous.

Worley's relatively short and unsuccessful career in piracy ended in a bloody battle in the bay of Jamestown, Virginia, where all but himself and one other were slain by the Governor's ships. Worley and his cohort were publicly hanged the next day—the 17th of February, 1719. (There is some dispute, however, over the accuracy of these claims, as other eye-witness accounts report that Worley died in battle along with the rest of his crew.)

"Calico Jack" Rackham

The flag designed by "Calico Jack" Rackham, an English pirate who was active during the early 1700s, was a variation on the basic skull-and-crossbones design, substituting two cutlass swords for the bones beneath the skull.

Why Is "Calico Jack" Famous?

In truth, Rackham was a fairly unsuccessful pirate, mainly targeting fishermen and traders. His fame is primarily due to two female pirates who served under his command—Anne Bonny and Mary Read. Unsurprisingly, female pirates were rare, especially ones as fierce as Bonny and Read, who matched their male counterparts in drinks, crassness, and combat. It is thanks to these women that history has remembered Rackham at all.

Blackbeard (a.k.a. Edward Teach)

One of the most dramatic of all pirate flags, Blackbeard's flag featured a horned skeleton holding a spear aimed at a heart that is dripping blood in one hand, while raising a toast to death with the other.

But contrary to popular belief, the real Blackbeard was not at all the way legends have made him out to be—wildly successful and bloodthirsty. In addition to being rather bad at plundering, he was also a fairly peaceful pirate. In fact, according to some accounts, Blackbeard didn't kill anyone until his last battle, when he was slain by Lieutenant Robert Maynard.

Yet the legend of bloodthirsty Blackbeard looms large even today. In one story, his decapitated body swam laps around the enemy ship that sported his head on the bowsprit before finally sinking from view.

Thomas Tew, the "Rhode Island Pirate"

The flag widely associated with Thomas Tew, an English privateer turned pirate from the late 17th century, depicts an arm holding a sword (although it has not been confirmed that Tew flew this flag). Unlike Moody's red flag (below), the black background on this flag suggests that violence could be avoided.

After a middling career privateering against Spanish and French vessels, Tew turned to piracy. Tew only made two major voyages as a pirate, however, the second of which ended in his bloody demise—he was reportedly disemboweled by a cannonball.

He is remembered for pioneering the Pirate Round—a sailing route used by many pirates in the 17th and 18th centuries.

John Phillips

A flag with a figure in the center, a pierced heart dripping blood on one side and an hourglass on the other has been attributed to 18th-century pirates John Phillips and John Quelch. Contemporary descriptions of Phillips' flag match this design, but less evidence exists that Quelch also used this design.

John Phillips began his seafaring life as a skilled ship carpenter. While aboard an English vessel bound for Newfoundland, his ship was captured by pirates, whom—as a skilled artisan—Phillips was forced to join. He had only served his new captain, Thomas Antis, for a year before running into trouble with a British Warship. He managed to escape, eventually finding his way back to Bristol and abandoning piracy . . . for a time.

Phillips quickly grew bored of life as a law-abiding citizen; in 1723, he stole a ship, renamed it the Revenge, and took to the sea as a pirate once more. Unfortunately for Phillips, his career as a pirate captain was short-lived. He was killed by his own prisoners in a surprise attack on April 18th, 1724.

Phillips is most well known for the "articles" found aboard his ship—one of only four extant sets of pirate code. Each code is unique to its captain. Phillips' nine articles are as follows (Fox, 324–5):

I. Every Man Shall obey civil Command; the Captain shall have one full Share and a half of all Prizes; the Master, Carpenter, Boatswain and Gunner shall have one Share and quarter. II. If any Man shall offer to run away, or keep any Secret from the Company, he shall be marooned with one Bottle of Powder, one Bottle of Water, one small Arm, and Shot. III. If any Man shall steal any Thing in the Company, or game, to the Value of a Piece of Eight, he shall be marooned or shot. IV. If any time we shall meet another Marooner that Man shall sign his Articles without the Consent of our Company, shall suffer such Punishment as the Captain and Company shall think fit. V. That Man that shall strike another whilst these Articles are in force, shall receive Moses’ Law (that is, 40 Stripes lacking one) on the bare Back. VI. That Man that shall snap his Arms, or smoke Tobacco in the Hold, without a Cap to his Pipe, or carry a Candle lighted without a Lanthorn, shall suffer the same Punishment as in the former Article. VII. That Man shall not keep his Arms clean, fit for an Engagement, or neglect his Business, shall be cut off from his Share, and suffer such other Punishment as the Captain and the Company shall think fit. VIII. If any Man shall lose a Joint in time of an Engagement, shall have 400 Pieces of Eight ; if a Limb, 800. IX. If at any time you meet with a prudent Woman, that Man that offers to meddle with her, without her Consent, shall suffer present Death.

While some pirates swore in their code on a Bible, apparently Phillips' men did so on a hatchet!

John Quelch flew the Flag of St. George—dragon-slayer and patron saint of England. Public Domain

John Quelch

While Quelch is often said to have flown the same flag as John Phillips, this is likely a myth. Evidence suggests that Quelch flew the Flag of St. George (pictured above) or a privateer-style variant thereof.

Though he was a fairly successful pirate, Quelch's career only lasted a year. He is mainly remembered by history as the first person tried for piracy under Admiralty Law outside of England (i.e., without a jury). (Admiralty courts were designed as a way to combat the rise of piracy in colonial ports where no other legal system seemed to be working.) Quelch was found guilty and sentenced to hang. Allegedly, he tipped his hat and bowed to his spectators from the gallows.

Edward "Ned" Low

Edward Low, a pirate known for being particularly brutal and savage, displayed a blood-red skeleton on a black flag. Those who saw this flag knew that a particularly grisly death would be theirs if they refused to surrender at once. With a youth spent thieving, gambling and beating up anyone who stood in his way, perhaps Low was predisposed to a life of piracy.

He was a strong young man and would often beat up other boys for their money. Later, as a gambler, he would cheat brazenly: if anyone called him on it, he would fight them and usually win. — Christopher Minster

When he grew tired of the landlubber life, he signed on aboard a vessel destined to cut logwood in the Bay of Honduras. Low soon became enraged at the captain and fired a musket at him (and missing). Naturally, the captain was displeased, and he marooned Low and several other discontented men in recompense.

Unwilling to accept their fate, the men captured a boat and became pirates, soon joining on with a larger pirate force under the command of George Lowther. Low was made lieutenant, and shortly promoted to captain of his own captured sloop. (All of this happened in a matter of weeks!)

Low enjoyed increasing success, eventually splitting from Lowther and becoming one of the most feared pirates in the world, robbing dozens (perhaps even hundreds) of other vessels. He was particularly ruthless and bloodthirsty, and his fearsome flag inspired terror in all who saw it.

It is not certain what happened to Low. He may have spent the remainder of his years living in Brazil or been set adrift by an incensed crew and eventually hanged in Martinique. No one knows for sure how Low met his end, but one way or another, his piratical ways came to an end in 1725.

Francis Spriggs, Low's Former Quartermaster

Low's former sailing partner Spriggs later struck out as a pirate captain in his own right and flew the same flag (or one very similar to it) on his ship, the Delight. Like Low, Spriggs was vicious and cruel, doing everything from making prisoners eat candle wax and go through "the sweats" to burning them alive on their own ships. Spriggs' ultimate fate is unknown.

Bartholomew "Black Bart" Roberts

The flag of "Black Bart" Roberts, who had particular animosity toward the islands of Barbados and Martinique because their governors sent pirate hunters after him, featured a figure of himself standing on two skulls, with the letters ABH (A Barbadian Head) and AMH (A Martinico's Head) beneath the skulls. In some variations of this flag, Roberts' sword is engulfed in flames.

In fact, this is just one of the four black flags associated with Black Bart. The other three are as follows:

a skeleton with an hourglass in one hand and crossbones in the other, with a spear and three drops of blood nearby

an hourglass held between a pirate and a skeleton

a skeleton and a man with a fiery sword

Though his contemporaries Blackbeard, Low, Rackham and Spriggs were all more famous, Roberts captured and looted more ships than all of them combined, making him the most successful pirate of the Golden Age of Piracy.

Christopher Moody's vibrant flag was known as "The Bloody Red". Bastianow, CC-BY-SA-2.5 via Wikimedia Commons - commons.wikimedia.org/wiki/File %3AFlag_of_Christopher_Moody.svg

Christopher Moody

One of the most distinctive pirate flags was flown by Christopher Moody—a former member of Black Bart's crew—during the 18th century. The flag's red color, along with the winged hourglass, arm holding a dagger and the skull and crossbones told Moody's prey that their time was running out and no lives would be spared.

In addition to his frightening flag, Moody is also reported to have flown red pennants from his ship's main mast—as if his no-quarter policy weren't already clear enough!

Moody was eventually captured and hanged in Ghana along with other former members of Black Bart's crew.

Stede Bonnet, the "Gentleman Pirate"

Though it uses many of the familiar symbols, Bonnet's flag is very unique in appearance. The heart and dagger represent life and death, while the skull acts as a scale.

An educated man who earned the rank of Major in the British army before becoming a prosperous sugar planter in Barbados, Bonnet was once a well-respected citizen in Bridgetown. His sudden turn to a life of piracy was, therefore, quite surprising to all who knew him.

Unlike most pirates, Bonnet did not steal his ship. Instead, he purchased a sloop, which he dubbed the Revenge, and paid his crew members out of his own pockets. Perhaps this is what earned him the moniker of the "Gentleman Pirate".

After an unfortunate run-in with Blackbeard, Bonnet changed the name of his ship to the Royal James and continued his life of piracy under a new name—Captain Thomas. But after capturing only a few ships, that career soon came to an end. Captain William Rhett, receiver-general of South Carolina, captured Bonnet (twice) and eventually put him to trial. He was executed on the 10th of December, 1718.

A Short-Lived (But Long-Loved) Fad

Flags with elaborate designs such as these were actually used for a relatively short period of time, with the first skull and crossbones appearing around 1700 and the Golden Age of Piracy ending by about 1740. The designs are so powerful, however, that they continue to be associated with piracy to this day.

References

Websites

Books

Konstam, Angus (Author), McBride, Angus (Illustrator). Pirates, 1660-1730. Oxford, UK: Osprey Publishing, Limited, 1998.

Rose, Jamaica and MacLeod, Michael. The Book of Pirates: A Guide to Plundering, Pillaging and Other Pursuits. Layton, Utah: Gibbs Smith, 2010.

Selinger, Gail and Smith, W. Thomas. The Complete Idiot's Guide to Pirates. New York: The Penguin Group, 2006.

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2012 Glen Nunes

The End on June 12, 2020:

What happens when this piracy ring of flagships and vessels gets exposed by yours truly

colleges rabelais on March 12, 2020:

there is very beautiful article it is very complated

damarcus 10 on December 06, 2019:

that cool

bob Tomas on September 19, 2019:

what

Hollywood7777 on May 06, 2019:

wow that is really cool!

Bob on September 16, 2018:

redbeards flag

BrianE01876 on August 06, 2018:

In Blackbeard's Flag the Skeleton isn't Raising a Toast, he's obviously holding a Hourglass. You can tell by the way he's flatly gripping the wide base. You don't hold a Wine Glass like that you hold a Wine Glass by the stem not the base. Also pirates didn't drink from wine glasses, they drank from probably Mugs mostly.

BTW nice page, I really enjoyed it and I'm from Massachusetts myself, the Spirit of America.!

Glen Nunes (author) from Cape Cod, Massachusetts on April 08, 2018:

whippoorwill: in response to your question, I believe the term Jolly Roger was a generic name that referred to any pirate flag. Thanks for the question.

whipoorwill on March 26, 2018:

Was'nt the skull and crossbones also called The Jolly Roger?

DJ on February 28, 2018:

Thanks for the information with the flags and who owned them.

harry on October 17, 2017:

put more flags on!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

Mashumi Qwabe on September 27, 2017:

Thanks I read something today, so all symbol and flags means something in this world?

Nug on August 28, 2017:

Who was the first pirate to fly the skull and crossbones flag (without the hourglass)?

Tyler on August 18, 2017:

This is very good one of the best i"ve see good job

kalae on February 10, 2017:

good research

wolfbanana on February 02, 2017:

cool. :)

Lee Cloak on March 09, 2015:

Very very interesting hub, lots of great detail,Thanks!

Glen Nunes (author) from Cape Cod, Massachusetts on July 16, 2013:

Thanks aj! I really appreciate it.

AJ Long from Pennsylvania on July 16, 2013:

Doc Sonic, thanks so much! I had no idea that these flags existed! I thought I knew about Pirates! So many flags, so few ships or pirates left to use them! Shared!! :o)

Geekdom on November 02, 2012:

That was an interesting read. I knew flags were used for signaling between ships but I never realized how complex and diverse it was.

Glen Nunes (author) from Cape Cod, Massachusetts on September 30, 2012:

Michael and Mhatter99, thanks for stopping by and commenting. It is much appreciated!

Martin Kloess from San Francisco on September 27, 2012:

Thank you for sharing this pece of history.

Michael Kromwyk from Adelaide, South Australia on September 27, 2012:

I thought that there was only the skull and cross bone before reading your article Doc Sonic. Imagine the feeling you would have had when you saw the more violent flags on the horizon! Cheers Michael