During the Golden Age of Piracy, pirates roamed the world, from the Indian Ocean to Newfoundland, Africa, and the Caribbean. Many ships were seized by legendary pirates such as Charles Vane and “Calico Jack,” Rackham, and “Black Bart Roberts,” who were easily recognizable by their pirate flags or “jacks” that they waved to friends and adversaries alike.
The sight of these pirate flags was enough to strike fear into the hearts of anyone who stumbled upon them, a testament to the power and influence of these notorious pirates.
Each of these flags bore a unique design, serving as a signature or seal for the pirate or privateer who committed the crime. The creativity and symbolism behind these designs were as diverse as the pirates themselves.
These flags, each with its own unique design and meaning, hold a significant place in history. The sight of these flags would send shivers down the spines of seafarers across different channels of the sea and oceans, a testament to their historical impact.
A Brief History of the Jolly Roger Pirate Flag
Although pirates were known as far back as 1650, the first Jolly Rogers were not flown until the Golden Age of Piracy. Bartholomew Roberts’s first pirate flags were not what we would expect from a modern Jolly Roger.
Bartholomew Roberts’ first flag was a cartoon of him sharing an hourglass and Death.
This was a Jolly Roger, no matter the appearance. The purpose was to communicate a message. Anyone who saw these pirate flags announced that their ship’s crew were pirates and that they would be granted mercy if they surrendered.
Many styles and variations of the skull-and-crossbones Jolly Roger flag have been created to create different pirate flags. Many pirates, including Christopher Condent, Black Sam Bellamy, and Edward England, have used it.
Let’s look at some of the most famous pirate flags and their history without further ado.
The Flag of Henry Avery
Henry “Long Ben” Avery had a brief but notable career as a pirate. He only ever seized a dozen or so ships, but one of them was none other than the Ganj-i-Sawai, the treasure ship of India’s Grand Moghul.
Long Ben’s seizure of the ship alone places him at or near the top of the list of the wealthiest pirates ever. He vanished not long after that.
According to mythology, he established his own country, married the lovely daughter of the Grand Moghul, and had his war fleet of 40 ships.
Avery’s flag depicted a skull in profile with a kerchief over crossbones.
The Flag of Bartholomew Roberts
Henry Avery was the most successful pirate in his day if you only consider the loot, but if you focus on the number of captured ships, then Bartholomew Roberts beats him by a mile.
Also known as Black Bart, he took 400 ships over his three-year career from Brazil to Newfoundland to the Caribbean and Africa, using multiple flags.
Black Bart was associated with the black flag, which featured a white skeleton, a white pirate, and an hourglass between them. In historical pirate flags, he was the first to signal that time was running out for his victims.
His most iconic flag, however, depicted him holding a sword and standing on two heads. Below him were the initials ABH and AMH.
The Flag of John Rackham
Calico Jack is a well-known English pirate. His career was more active when the Golden Age of Piracy was ending. Calico Jack and his crew terrorized the Caribbean Sea.
Because it is one of the most famous historical pirate flags (considering it is a Jolly Roger variant), his flag is even more remarkable. Rackham’s version replaces the bones with swords. The original Jolly Roger was a black flag with two crossed bones and a white skull underneath. The swords were intended to signal that the pirate and his crew were prepared to use violence if the attacked vessel didn’t surrender.
His flag would eventually become the most iconic pirate flag in modern culture.
The Flag of Stede Bonnet
Bonnet was a wealthy English landowner before he turned to piracy in the 18th century. He often attached ships to the Atlantic and Caribbean Seas. Because of his previous status as a highly-ranking member, he was usually called “The Gentleman Pirate.”
Bonnet’s flag had a black skull and a white skull with a bone in its middle. On either side of this skull was a dagger or a heart, representing the scale of pirate justice.
The Flag of Edward Low
After the Golden Age of Piracy, another 18th-century English pirate, Edward Low, rose to notoriety. Low is well renowned for his brutality and cold-bloodiness. From 1722 to 1724, he assumed command of nearly 100 ships in only two years.
Low’s flag was one of the interesting pirate flag designs— and was used as a warning to other ship crew members that their deaths would be excruciating. Low flew a black Jolly Rodger adorned with a red Skeleton. This was to signify Low and his crew’s anger and sheer evil and that a violent and bloody end was near.
The Flag of Thomas Tew
Thomas Tew was an English pirate from the 17th century who was known as “The Rhode Island Pirate.” Before his career in piracy, he was a privateer. His most famous accomplishments are his two major pirate cruises. He died on the second cruise.
His flag is free from most Jolly Roger imagery, except for the background of the black flag. His flag is instead a hand holding a knife — one of the universal symbols of violence.
Tew’s warning was well-received. Although He had only been a pirate for three years, he had amassed approximately 1 million dollars in today’s currency by the time he died.
The Flag of Edward Teach
“Blackbeard” was Edward Teach’s second most famous name. He was known for his tricks and commanding ships with fear and force.
Legend believes that he would light fuses in his hair and then give off a demonic appearance to instill fear in his enemies.
The Blackbeard flag featured a horned skull holding a spear in one hand and making a toast with the other. It was pointed at a blood-red heart. The Blackbeard flag was designed to look devilish and indicate that he would be a slow, torturous death to all who attacked him.
Raise Your Flag on Sunshine Scenic Tours’ Pirate Ship
Experience what Blackbeard, Henry Avery, or any famous pirates felt while cruising the seas with their pirate flags displayed for others to be wary of with Sunshine Scenic Tours. We have everything you need to see what sailing on a pirate vessel is like.
Sunshine Scenic Tours offers a thrilling pirate cruise in John’s Pass and nearby areas. Contact us for inquiries or reservations! We are looking forward to making your Florida vacation unforgettable.
