Top 15 Most Famous Pirate Flags And Their Meanings

Almost since the end of the Golden Age of Piracy in 1720, pirates have captured the imagination of the public. When it comes to pirates, perhaps nothing has captured people’s attention more than one of the most famous pirate flags in existence, the Jolly Roger. But what does the pirate flag mean?

Pirates Symbols and Meanings

Symbol	Meaning
Red Pirate Flag	Warning sign for no mercy
Skull and Bones	Death
Bleeding Heart	Slow painful death awaits you
Edward Low (red skeleton)	Torment with eventual death
Hourglass Symbol	Time is running thin
Nude Pirate	Pirates with no shame
Clothed Pirate	Most likely stood for pirate captain
Lifted Drinking Glass	A toast to dying or to Satan
Horned Skeleton	Satan
Weapons	Incoming fight

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A Short History of the Jolly Roger Pirate Flag

While pirates had been around as early as 1650, the first Jolly Rogers weren’t flown until after the Golden Age of Piracy. These first flags, flown by Bartholomew Roberts and Francis Spriggs, looked nothing like what we would expect a modern Jolly Roger to look like.

For example, Francis Spriggs’ flag was a red skeleton on a black flag. Bartholomew Roberts’ first flag was a caricature of him sharing an hourglass with Death.

No matter how they looked, all Jolly Rogers had one purpose: to send a message. They announced to anyone who saw them that the crew of the ship was pirates and that if they surrendered, they’d be given mercy.

The earliest use of a black flag with a white skull and crossbones is credited to the French pirate captain Emanuel Wynn in 1700. Wynn’s flag also used an hourglass image to symbolize that whoever saw it was running out of time. This hourglass image was then picked up by other pirates and appears on several other flags.

The skull-and-crossbones design of the Jolly Roger flag has been used in many different styles and variations. Many different pirates have used it, including “Black Sam” Bellamy, Christopher Condent and Edward England. We’ll take a look at the top ten most famous real pirate flags of all time.

15. Olivier Levasseur

Levasseur has had more than one flag attributed to him. They all include black and white designs. A very popular one has a black skeleton on a white background. This makes it one of the few black on white pirate flag designs rather than the other way around.

Levasseur was a French pirate also known as “The Buzzard” or “The Mouth”. This comes from his reputation for verbal insults. He was also known for having a large treasure with cryptic clues to its whereabouts. This has inspired much lore about pirates and treasure hunters over the years.

While many pirates gave up their piracy for amnesty, Levasseur refused to because he would have had to give back much of his treasure. This caused him to secretly settle on some islands. He was eventually captured near Madagascar and hanged for his crimes at Saint-Denis in 1730.

14. Jacquotte Delahaye

This flag showcases a woman and a skeleton dancing over a heart. The inclusion of a woman is because Jacquotte Delahaye was a woman pirate. She was, however, also believed to be fictional. This is because there are no firsthand stories of Delahaye.

Her character was given an interesting background of a French father and Haitian mother. She turned to piracy when her father was murdered, and her mother suddenly died. Delahaye faked her death and donned a male alias. These tales are likely the imaginations of fiction writer, Leon Treich, who is responsible for many of her stories.

Her fabricated history also included having red hair, resulting in the nickname “Back from the Dead Red”. She was given a Hollywood-style death in a shoot-out defending the island of Tortuga.

13. Brethren of the Coast

The design of a skull with two swords in a cross position is now attributed to the Bretheren of the Coast. Instead of being the flag of one pirate, it’s now the flag of a group of them. The Bretheren of the Coast was a coalition of pirates who roamed the Atlantic, Caribbean, and Gulf of Mexico in the 17th and 18th centuries.

The Brethren of the Coast was headquartered on the island of Tortuga and Port Royal. The pirates in the group had a code of conduct to follow, authority, rights, and divisions of earnings. This association is now connected with the Pirates of the Caribbean film series where a fictional version of the Brethren figures into the plot.

12. Christopher Condent

Christopher Condent’s pirate flag shows three skulls and crossbones across the flag. While this flag is now connected to Condent, its history with the famous pirate is unclear. The design first appeared in the Mariner’s Mirror magazine in 1912, but it wasn’t credited as Condent’s. It would later be contributed to Condent when it began showing up in other publications. There is only one period source describing his flags as having “Deaths Hand on them”.

The real name of Christopher Condent is not officially known. He was, however, given the nickname of “Billy One-Hand”. He was a ruthless pirate known for cutting the ears and noses off his prisoners . He was later pardoned by the French governor and settled in Bourbon. He married the governor’s sister-in-law and worked as a merchant.

11. Black Sam Bellamy

The Black Sam Bellamy flag depicts a skull and bones often associated with pirates. This one is just a plain skull on top and two crossbones below with a black background. While this is the flag now linked with Bellamy, the historical accuracy is debatable.

Some sources cite the flag as the standard skull and bones design while others depict a heart and dagger. Either way, the skull and bones artwork is now connected with Black Sam. Bellamy got the nickname “Black Sam” for his long black hair.

Bellamy was known as the Prince of Pirates for his gentlemanly and fair demeanor. He was also considered the wealthiest pirate, even though his career only lasted a year. He turned to piracy to win enough money to satisfy the parents of Maria Hallett so he could marry her. His ship, the Whydah Gally, sank. It’s considered the first authentic pirate shipwreck to be discovered in 1984.

10. Francis Spriggs/Edward Low

Spriggs’ flag was one of the first flags to be called a Jolly Roger. However, it lacks almost all of the symbols we’ve come to associate with Jolly Rogers. The design of Spriggs’ flag, a red skeleton on a black flag, doesn’t even originate from him. Instead, it comes from one of Spriggs’ former sailing partners, Edward Low.

Although it’s unknown when Spriggs began his career of piracy, he and Low had split by Christmas of 1724. Spriggs then took his ship, the Delight, and set sail for the Caribbean.

Francis Spriggs was still active by April of 1725, when he set some of the crew from his Caribbean conquests free on the island of Roatan off the northern coast of Honduras. He and his crew captured several more ships around Bermuda and Saint Kitts later that year. His ultimate fate after 1725 is unknown.

9. Stede Bonnet, “The Gentleman Pirate”

Bonnet’s flag is traditionally thought to have been a skull over a horizontal long bone and between a heart and a dagger (shown below). However, there is no contemporary source for this having been his flag. The earliest source listing this is from an unknown, undated manuscript that was gifted to the Maritime Museum of Britain in 1939.

Contemporary sources say that Bonnet flew either a dark red flag or a flag with a death’s head on it. If Bonnet did indeed use the flag that popular culture had associated with him, it would have had a very clear meaning. The heart and dagger represented life and death, with the skull and bone being a crude approximation of a scale.

8. Christopher Moody

Moody is yet another pirate who completely eschews the standard conventions of the Jolly Roger that we’ve come to know. Operating from 1713 to 1718 in the waters around North and South Carolina, Moody was a particularly bloodthirsty pirate. His flag, shown below, only confirms that.

Instead of the traditional white designs on a black background that most pirates favored, Moody chose designs picked out in gold on a red background. The use of a red background is particularly ominous. Among pirates, privateers and naval captains, flying a red flag often meant that no quarter would be given.

Add this to the designs on Moody’s flag — an hourglass with wings, representing time flying away; an arm holding a dagger; and a gold skull with crossed bones — and you get a flag that is particularly chilling to see coming closer to you on the horizon.

7. Emanuel Wynn

Wynne is one of the first to fly a Jolly Roger pirate flag as we know it today. His flag consisted of a white skull over crossed bones with an hourglass underneath. This was a symbol to anyone who saw it that time was running out and that they could only avoid death by surrendering.

One of the few contemporary descriptions of Wynn’s flag comes from Captain John Cranby, who commanded the HMS Poole. The Poole attacked Wynn off the Cape Verde islands in July of 1700. Cranby’s description is as follows: “a sable ensign with cross bones, a death’s head, and an hour glass.”

Following the attack by the Poole, Wynn left the Cape Verde islands for the Caribbean and more profitable raiding opportunities, attacking British and Spanish shipping. His eventual fate is unknown.

6. John Quelch

When it comes to the pirate flags on the list, John Quelch’s flag stands alone. That’s because it isn’t really a pirate flag at all: it’s the national flag of England. Before beginning his career of piracy, Quelch sailed on the English privateer ship Charles as its lieutenant. In July of 1703, the crew mutinied and elected Quelch as the new captain.

Quelch immediately sailed south for the Portuguese colony of Brazil. By the time the crew returned to their original port of call, they had over £10,000 in goods in the hold. Quelch’s prize is equivalent to about $2,416,024 today.

However, the Portuguese were not valid targets for Quelch to privateer. He was arrested and sentenced to death through an Admiralty trial — the first of its kind in America. Quelch was hanged on June 30, 1704 in Boston.

5. Thomas Tew

The flag of Thomas Tew eschews most of the standard Jolly Roger imagery except for the black flag background. In its place, his flag is an arm holding a cutlass — one of the most universal symbols of violence out there.

Tew’s use of a cutlass was a pretty unambiguous warning. He wouldn’t hesitate to kill anyone who stood in his way, so his enemies should just surrender. The warning was well-heeded: even though Tew was only a pirate for three years (1692 – 1695) he had managed to amass a wealth of about £8,000 ($1,651,137.49 today) by the time he died in 1695.

4. “Calico Jack” Rackham

Rackham was made famous thanks to his portrayal in the Starz TV show “Black Sails” and the video game “Assassin’s Creed IV: Black Flag”. However, he was not actually active as a pirate for very long — only two years (1718 – 1720).

The first record of Rackham participating in piracy comes from 1718, when he was quartermaster aboard Charles Vane’s ship Ranger. After Vane was removed from captaincy of the Ranger, Rackham was voted to the captaincy. He would command several vessels throughout his time as a pirate, most notably the Kingston. No matter which ship he commanded, Rackham would use the same exact Calico Jack flag: a skull above a pair of crossed swords (shown above).

3. Henry “Long Ben” Every

One of the more famous pirates on this list, Every captured the attention of both contemporary and modern audiences. Although he was only active between 1694 and 1696, Every holds the record for the largest heist of treasure ever pulled in by one pirate crew.

In a raid on Mughal merchant ships in 1695, Every and his crew pulled in a treasure worth 300,000 to 600,000 British pounds — the equivalent of 50 to 120 million US dollars today. Following the raid, Every largely vanished from public life. All records of his location and activities cease to exist after 1696 — including what he did with his shares of the Mughal treasure.

2. Bartholomew Roberts

Even though he was only a pirate for three years, Bartholomew Roberts is perhaps the most successful pirate on this list. From 1719 to 1722, Roberts captured over 400 prizes.

Roberts began his career of piracy June of 1719. The ship he was on was captured by pirates under Howell Davis. The pirates forced Roberts and several of his men to join them. Then they set sail for the island of Principe off the west coast of Africa.

At Principe, Captain Davis was shot dead by the Portuguese garrison, who had found out that he and his crew were pirates. With Davis dead, a new captain had to be elected — Roberts.

Although he initially had not wanted to join the pirates, Roberts accepted his promotion to captain. He reasoned that if he was going to be a pirate, it was better to be captain than a common man.

After his election to captain, Roberts drew up his first flag (shown below), which showed him together with Death, holding an hourglass.

Roberts is the only pirate to have used two flags, both of them famous pirate flags in their own right. While the first came soon after his election to captaincy, the second wouldn’t come until February of 1720. Roberts found himself pursued by two pairs of sloops, one from Barbados and one from Martinique. He swore vengeance against the inhabitants of both islands and had a new flag drawn up (shown below). On it, he was standing over a pair of skulls: one labelled ABH (A Barbadian’s Head) and the other AMH (A Martiniquian’s Head).

1. Edward “Blackbeard” Teach

Without a doubt the most famous pirate on this list, Edward Teach, also has the distinction of having one of the most famous pirate flags on this list.

He has become who most people think of when they hear the word “pirate”. Teach and his first ship, Queen Anne’s Revenge, have been made famous thanks to their portrayal in media such as “Sid Meier’s Pirates!” and “Assassin’s Creed IV: Black Flag”. The Blackbeard flag, shown below, is almost as famous as Blackbeard himself is.

The Blackbeard Flag Meaning

Depicting a skeleton raising a toast while spearing a heart, the Blackbeard flag is almost certainly meant to intimidate one’s enemies. However, there is not as much information on the Blackbeard flag meaning.

Historians dispute that the flag publicly accepted as Blackbeard’s is actually his. The first mention of the flag that would later be accepted as Blackbeard’s is in 1912. The most widely-accepted contemporary source, “A General History of the Pyrates,” doesn’t even list Blackbeard as having a particular flag. The woodcut of his ship included with the book is simply flying a regular flag.

This hasn’t stopped the public from embracing it, however. The state of North Carolina flew Blackbeard’s flags from its ferries in 2018 to celebrate the 300th anniversary of the battle of Ocracroke Island and Blackbeard’s death.

If you’re looking to get your own Jolly Roger, or to design a custom flag, head over to the Vispronet.com webstore and pick one up today!

Sources

1. 1. Infamous Pirates — Francis Spriggs: https://goldenageofpiracy.org/pirates/francis-spriggs.php
   2. At The Point Of A Cutlass: https://books.google.com/books?id=VWG0AwAAQBAJ&printsec=frontcover#v=onepage&q&f=false
   3. Francis Spriggs: https://www.thepirateking.com/bios/spriggs_francis.htm
   4. Pirates — Christopher Moody: https://www.crwflags.com/fotw/flags/pir-mody.html
   5. The Biography of John “Calico Jack” Rackham: https://www.thoughtco.com/biography-of-john-calico-jack-rackham-2136377
   6. The Trials of Joseph Dawson, et al: https://catalog.loc.gov/vwebv/search?searchCode=LCCN&searchArg=19011844&searchType=1&permalink=y
   7. Henry Every’s Bloody Pirate Raid: https://www.history.com/articles/henry-everys-bloody-pirate-raid-320-years-ago
   8. A General History of the Pyrates: From Their First Rise and Settlement In The Land Of Providence To The Present Time: https://books.google.com/books?id=oipEAQAAMAAJ&pg=PA230#v=onepage&q=AMH&f=false