Pirate Flags

Stupid Question ™
April 4, 2005
By John Ruch
© 2005

Q: Did pirate ships really fly pirate flags? If so, why? Wouldn’t they want to be stealthy?
—anonymous, Chicago, Illinois


A: Pirate ships indeed flew flags—variously a red flag, a black flag, and/or the infamous “Jolly Roger,” a black or red flag with some morbid motif.

But they didn’t sail around all the time with this dead giveaway flying. The flag would be hoisted at the last minute prior to engaging with a victim ship. The idea was to sneak up and then instill hopeless fear so the ship would peacefully surrender—which often happened. As Stuart A. Kellen’s puts it in his book “Life Among the Pirates,” the pirate flag spoke “the universal language of fear.”

At least one pirate elaborated this by playing martial music—drums and trumpets—at the time of assault.

At a time in which the vicious nature of most pirates was common knowledge, the flag was very effective.

While the language may be universal, the flags weren’t. The classic Jolly Roger is known only from 1700, especially in the Caribbean. Before that, and in other areas, many pirates simply flew national flags (not surprisingly, since many were privateers paid by national governments to disrupt shipping).

Still, the red flag was popular fairly early, raised as a blood-colored sign to indicate an intention to fight. The black flag had similar effect, with connotations of death.

The first known Jolly Roger was sighted around 1700 in the Caribbean flying on the ship of a little-known French pirate, Emanuel Wynne. It was a black flag bearing a skull with crossed bones behind it, and beneath it an hourglass.

Pirates did not invent such symbolism. In fact, most of their designs were common on gravestones of the era, which emphasized an awareness of the shortness of life. The hourglass indicated the fleeting nature of time.

There were many variations on the Jolly Roger, with each pirate crew having its own, much like a gang logo. Edward “Blackbeard” Teach’s flag had a devil-headed skeleton with an hourglass in one hand and a spear in the other, which was jabbing at a red, bleeding heart.

Christopher Moody’s flag was red and featured a winged hourglass, an arm wielding a dagger and a skull and crossbones.

The now-classic design of a skull with bones crossed beneath it, on a black background, was the flag of Edward Seegar, aka Edward England, who flew it from 1717 to 1720. In fact, England wasn’t so bloodthirsty; he ended up marooned by his own crew for showing too much mercy to a captured captain. He was undoubtedly sympathetic, since he himself was originally a captive who chose to join the pirate crew.

The term “Jolly Roger” is first found in print in the late 1700s. It’s unclear if pirates ever actually used it themselves. In any case, it’s a playfully morbid personification of the skull on the flag as a pirate himself.

“Jolly” at the time had connotations not only of fun-loving and agreeable, but also of drunkenness and lust. “Roger” was a generic term for a man, as well as slang for “penis.” “Old Roger,” a slang term for Satan also based on the generic-male usage, may have been an influence.

Pop etymologies that attribute “Jolly Roger” to a corrupted French phrase or Indian name should be made to walk the plank.