The Jolly Roger flag is most readily identified with the golden age of piracy. But a number of different flags and designs were used, and not just the iconic skull and crossbones. 

The practice of flying a Jolly Roger flag first appeared in the 1710s. It signified that a pirate ship was about to attack. 

The Beginnings of the Jolly Roger Flag

There is some disagreement between historians about the history of the term “Jolly Roger.” The first use of the term in print appears in 1724 in Charles Johnson’s The General History of Pyrates. (The book is now attributed to Daniel Dafoe, who wrote Robinson Crusoe).

Some historians point to the French “joli rouge” as the name’s origin. There are others who believe the term “Roger” or “Old Roger,” comes from the common 18th-century nickname for the devil — and the grinning skull inspired the name.

The red flag was used widely during the pirate era. A red flag would indicate that no quarter would be given if a fight broke out during the pirates’ attempt to capture a ship, whereas a black flag meant that quarter may be given. Many pirate ships would display false colors as they approached unsuspecting targets. Once close, they would hoist the pirate flag to frighten ships into surrender. 

Pirates have been preying upon the seagoing merchant fleets since the earliest days of trade.

During the Roman Republic, the trade routes of the Aegean and Mediterranean were preyed upon by Cilician pirates. These pirates were not only tolerated by the Romans, but they also traded slaves with them. However, once the Cilicians threatened Rome’s grain supply in 67BC, they were severely dealt with. 

After Columbus discovered the New World, pirates began preying upon Caribbean shipping. Gold, silver, sugar, and human cargoes were ripe for the picking with an abundance of good ports for the pirates to operate out of. 

While the common perception is that the captain reigned with absolute power, on many pirate vessels, the captain served at the whim of a council governed by the crew. So, if a captain was too strict or cruel with the crew he could be removed. 

Many pirates first served at the behest of their government, plundering ships from enemy countries. Such was the case with the famed English pirate Henry Every. He was distinguished as a “noble pirate,” a title also bestowed upon the likes of Sir Francis Drake and Sir Henry Morgan (whom the book Captain Blood was based on) in recognition of their efforts on behalf of English maritime interests.

In Charles Johnson’s book, he wrote about two pirate captains that had called their flag Jolly Roger – Bartholomew Roberts in 1721 and Francis Spriggs in 1723. What is noteworthy at the time was that although both captains used the term “Jolly Roger” in describing their flags, neither flag had a skull and crossbones on it. 

The Different Designs of the Jolly Roger Flag

One man who was captured by pirates testified that after his capture in 1724 he witnessed a pirate flag with a skeleton stabbing a heart with a spear, which the pirates called “Jolly Roger,” being risen on the ship’s mast. So, the term was generic rather than describing an exact flag design.

The first recorded uses of the now infamous skull-and-crossbones originated among the Barbary pirates of the 17th century. They used the black color of the Jolly Roger to the Muslim Black Standard. 

Francis Drake’s reportedly was flying a black flag as early as 1585, but historians have argued that that was inaccurate. A plain black flag was also attributed to Blackbeard, Charles Vane, and Richard Worley in 1718, and Howell Davis in 1719. Blackbeard was also attributed to using the skeleton with a spear stabbing a heart. 

Modern Use

The Jolly Roger flag is still in use by modern navies although its meaning is quite different from those pirates of 300 years ago. With the advent of submarines and submarine warfare in the early 1900s, First Sea Lord of the British Royal Navy Admiral Sir Arthur Wilson stated that submarines were “underhanded, unfair, and damned un-English.” He vowed to have the crews of enemy submarines captured during wartime hanged as pirates.

However, at the beginning of WWI, the British submarine HMS E9 successfully torpedoed the German cruiser SMS Hela. In typical British fashion, HMS E9’s commanding officer Max Horton instructed his crew to manufacture a Jolly Roger. The flag was flown from the submarine, as she entered port.

A few other subs began the practice of flying the Jolly Roger upon returning from a war patrol after having torpedoed an enemy vessel.

The practice would continue in WWII.

In a sea engagement during the Falklands War in 1982, the British submarine HMS Conqueror flew the Jolly Roger after slamming three torpedoes in the Argentine cruiser General Belgrano, causing her crew to abandon ship within 20 minutes. 

Cmdr. Chris Wreford-Brown, the captain of the Conqueror, later said of the sinking:

“The Royal Navy spent 13 years preparing me for such an occasion. It would have been regarded as extremely dreary if I had fouled it up.”

Twice in 2017, the USS Jimmy Carter, an American attack submarine modified to support special operations forces, returned to its homeport flying a Jolly Roger indicating a successful mission.