Famous Pirate Flags: Beyond the Skull and Crossbones

Pirate Symbol and Flag Meanings

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 (or infamous) pirates in history.

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

When used by pirates, the red flag 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 Pirate Flags 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.

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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

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

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, 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):