Are pirates cool?
“To Err is human. To Arr is pirate.” I saw that on a t-shirt yesterday.
A fairly large percentage of recreational boaters fly pirate flags—the Jolly Roger or some variation. They fly them because they look cool, but this is a touchy subject among sailors.
Take these headlines:
“American Yacht Captured by Somali Pirates – Crew Hostage”
"Somali pirates anchor Danish family yacht, threaten death"
“Couple held hostage by Somali pirates for more than a year”
That’s not cool. That’s the opposite of cool. That’s the least cool thing that could ever happen to a sailor.
Today’s pirate flag flyers obviously don’t support that kind of piracy. Their message is more like “Rum drinks may be served on this vessel without warning…yo ho ho.”
Today’s pirate flag flyers are giving a nod to the spirit of piracy during the Golden Age of Piracy, about 300 years ago. So after a few hundred years murder, theft, and hijacking become romantic and cool?
Do Somali pirates fly pirate flags? Did pirates hundreds of years ago even fly pirate flags? It seems like the element of surprise would be a big part of piracy, and you wouldn’t want to have a big flag visible at 500 yards that said, “Guess what? We’re pirates and we’re coming toward you.”
It turns out pirates of old really did fly Jolly Rogers to distinguish themselves from privateers and other government vessels that roamed the seas and took other ships as prizes. The “legitimate” prize-taking vessels were bound by rules of engagement that prevented them from torturing, raping, or just killing everyone aboard. True pirates were bound by no such rules, and announcing this with a flag was often enough to make the other ship surrender without a fight.
The first pirate flags were probably red, or the black and red flags might have each had their uses. Jolly Roger comes from the French joli rouge, the happy red, because the red flag meant a ship would fight to the death and neither give nor expect quarter. Not very happy. Let me digress in saying that while it sounds exciting, salty, and romantic, had I or the average pirate flag flyer of today lived in those times we probably would have got ourselves jobs as clerks in the customs house.
A pirate’s motivation was to take the prize with as little damage as possible to his own ship, the prize, or his own men. Wounded men or a ship with a cannonball hole in it (either the pirate ship or the prize) were not good for the pirating business. A pirate’s bread and butter was built on a reputation for “surrender or die,” but of course he always preferred surrender. Once the reputation was established that a resistant crew would be annihilated and a surrendering crew would be given mercy, the pirates had it just the way the wanted: fly the jolly roger, the prize surrenders, pirates take the booty, nobody gets hurt.
So ironically, rather than suggesting a sadistic desire to murder, torture, and fire broadsides, the Jolly Roger signaled the pirate’s motivation to avoid conflict and to reach a peaceful hand-over of the prize…which brings us right back to our pirate flag flyer of today, who also has a strong desire for peace, mai tais, and Jimmy Buffet.








