Maritime flags had long been used to communicate from vessel to vessel at sea and were used for centuries before the first sighting of the infamous 'Jolly Roger' emblem in the early 1700s, or “Golden Age of Pirates”. Typically pirate vessel wouldn't fly “colors” (flags) at all times, they would wait until they were in attacking range of another ship and hoist their flag as an ominous warning of what was to come. Pirate captains took this form of communication to show off their own personal brand of piracy, with many of the symbols shown having a deeper meaning. Below we shed some insight on some of the historical pirate styles we carry.
Not too much is know about Emanuel Wynne, but he was considered the first pirate to fly a Jolly Roger flag. Though the skull and crossbones design was used by many seafaring pirates, Wynne added an hourglass motif to signify that the ship under attack only had a short amount of time to surrender.
Edward Teach, better known by the fearsome moniker Blackbeard, is the most famous pirates of the 'Golden Age'. His nickname came from his appearance, his long black beard covered most of his face. Blackbeard kept himself well armed, often wearing a sling that housed three pairs of pistols and a plethora of knives. Most surrendered at the sight of the notorious captain, but he was known as being cooperative to those who surrendered quickly. His flags depicts a horned skeleton, holding a glass in one hand and a spear aimed at a heart. This was to mean that Blackbeard himself was a sort of devil who toasted to death and wasn't afraid of violence.
Edward Lowe had a short career span of only 3 years, but in that time frame he was able to gain a reputation as being the most violent pirate on the seas. He grew more brutal over the course of his career, bringing unwanted attention from the Caribbean government who quickly dispatched to capture Lowe. He and a skeleton crew managed to escape but historians still dispute his fate; Some say he was marooned on an island by his crew, found by the French and executed in Martinique, others say he escaped to Brazil and lived out the rest of his days. Regardless of his fate, the message his flag conveyed was obvious, a blood red skeleton on a black background meant to give heed to those who saw it: death would be brutal and swift if they did not surrender immediately.
C. Condent was known by many names but was more notoriously known as One-Hand-Billy. Over the course of his piracy career Condent seized many ships in the Indian and Caribbean oceans, although he wasn't considered one of the most memorable pirate captains of the 'Golden Age of Pirates' he was one of only captains to have a comfortable life post-seafaring. Condent became a merchant and lived the rest of his life as a wealthy man until his death.
Christopher Moody was infamous for his 'No Quarter' policy, meaning he didn't spare the lives of prisoners. With the blood red color, a winged hourglass, skull & crossbones and a dagger clad arm; his policy was clearly communicated to fellowships he attacked: Their time was running out and no lives would be spared.
Henry Avery was known as 'The Successful Pirate', he began his career on a Spanish gun ship named 'Charles II' where he led a mutiny that resulted in him being named Captain. Henry Avery's history is steeped in mystery but the legend says he retired with his large bounty after only a year of pirating under an assumed name, giving clout to his moniker.
Stede Bonnet lived as a wealthy plantation owner in Barbados until the day, without warning, he decided to turn to a life of piracy. He was originally known as the 'Gentleman Pirate' due to his substantial upbringing and manners, but quickly became known as an incompetent pirate as he had no previous sailing experience. Though, in a stroke of luck, he made a power ally in the fearsome Blackbeard; who thought of Bonnet as polite and well spoken. The alliance lasted until Blackbeard left him with only a ship and small crew marooned on a small island.
Jack Rackham, better known as 'Calico Jack' to his fellow pirates, was a member of the 'Golden Age of Pirates'. Although he sailed during the time period of high piracy he was not remembered for being a particularly good fighter or a navy strategist, he was more so known for his backstabbing politics. He was also of the first pirates to fly what is now considered a standard 'Jolly Roger' with a prominent skull and two objects crossed below in, in this case two cutlasses.
John Quelch, a lieutenant turned pirate, was infamous for being the first to be tried for piracy outside of England. He and his crew, upon being found guilty were marched to the gallows where all but Quelch showed remorse for their actions.
Edward England, a sailor turned pirate, sailed the seas in the early 1700s when piracy was rampant. England was revered as one of the more humane pirates of the Golden Age, though his flag displays crossed swords which meant a willingness to fight.
Jean Thomas Dulaien sailed the Caribbean seas in the early 1700s. He became famous for his version of the Pirate Code, which included parameters for all aspects of pirate life from deserters to splitting loot. After attempting to leave his crew stranded with no loot, he was denied pardon by French officials and was taken to jail, his fate remains unknown.
Richard Worley was a sailor in Queen Anne's war, quickly becoming tired of the hostilities he turned to a life of Piracy. While his career as a pirate only lasted a mere 6 months he has left a lasting impression in history, as he and his crew wrote the infamous 'Pirate Code' and began use of the pirate flag motif most are accustomed to.
Black Bart was considered 'The Most Successful Plunderer' of the Golden Age of Pirates and was known to be a particularly cruel as he had burned 20 ships over the course of his plundering career. In particular he had a special hatred for the Caribbean Islands of Martinique and Barbados, which is why his flags shows him standing atop two skulls ABH (A Barbadian Head) and AMH (A Martinician's Head).
Thomas Tew was one of the most notorious pirates of the Red Sea. He was mentioned by name in a warrant issued by King William III, and was noted as a "wicked and ill-disposed person". His flag is emblazoned with an arm holding a cutlass, meaning a willingness to fight but the black background color symbolized that violence could be avoided.
The Brethren of the Coast was a loosely held together coalition of Pirate Captains and Privateers of the time. The Brethren was formed during the 'Golden Age of Pirates' in the early 1700s, this group regulated the privateering at the time and attempted to uphold the 'pirate code' amongst themselves.