Did Pirates Really Sail With A Jolly Roger Flag?

Despite there being thousands upon thousands of flag designs, perhaps the most famous, the one that first comes to mind for many people and a popular seller at our flag shop, is the Jolly Roger, the skull and crossbones that struck terror throughout the seven seas.

From Robert Louis Stevenson’s Treasure Island to One Piece, there have been endless depictions and variations on the Jolly Roger flag in fiction, which has often led to questions about whether they were actually flown.

Did pirates actually fly the Jolly Roger? How did it look? How was it used? And who actually is Roger?

Did Pirates Use The Jolly Roger Flag?

Whilst it seems stranger than fiction, there are at least two surviving examples of flags with the classic skull and crossbones design, both of which date back to the 1700s. One is currently based in the Aland Maritime Museum in Finland, whilst the other resides in Portsmouth.

The black pirate flag, sometimes known as the ‘death’s head’, had been used for over a century by that point, with at least one contemporary account from 1687 describing a red flag with the skull and crossbones design similar to the one found in Portsmouth.

Part of the reason why it was adopted so much is that many pirates were part of a large group that standardised many aspects of piracy, including the adoption of the flag.

Did All Jolly Roger Flags Look The Same?

Whilst there were standard designs and the skull and crossbones had been widely adopted by 1730, most Jolly Roger flags tend to have quite significant differences from each other.

There was a range of other elements besides the death’s head that were used, including:

• A full human skeleton, sometimes holding a spear and stabbing a heart.

• An hourglass.

• Swords, sometimes crossed together like crossbones.

• A sword arm.

• Pistols, sometimes crossed together.

• Cannons.

• Horns.

As well as this, whilst black flags were the most common and many pirate ships also had a red variation, it was not unheard of to see blue, green, white, yellow, or flags with red and yellow stripes. Some pirates even used variations of national flags.

How Was The Jolly Roger Used?

Unlike modern pirate stories, where the Jolly Roger was a proud signifier of identity, the black flag was only flown when close to other ships in order to tell other nearby ships who and what they were.

Either this was to let other pirates know of their identity or to give targeted ships a chance to take down their flag and surrender without risking their lives.

In general, this is why most pirates had at least two versions of the Jolly Roger:

• A black flag was a symbol of “quarter”, meaning that a ship that surrendered would be given mercy for its cooperation.

• A red flag, however, signified “no quarter”, and that if the pirate ship were to attack, no lives would be spared. Red flags were not exclusively used in piracy, but variations with death’s head motifs were.

In general, a pirate would either not fly a flag at all or use a false flag of a nation they did not belong to. Owning a Jolly Roger was a crime punishable by execution in the Golden Age of Piracy, so having the flag was generally seen as proof one was a pirate.