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7 Most Notorious Pirate Flags and Their History

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.

Pirate flags were used to intimidate anyone who stumbled upon them. These flags were also used to distinguish the pirate or privateer who committed the crime. It was the Jolly Roger holder’s signature or seal on their ship.

The following list features seven famous pirate flags, the sight of which would frighten seafarers across different channels of the sea and oceans.

A Brief History of the Jolly Roger Pirate Flag

Although pirates were known as far back as 1650, the first Jolly Rogers was not flown until the Golden Age of Piracy. The first pirate flags flown by Bartholomew Roberts 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 the crew of their ship were pirates and that they would be granted mercy if they surrendered.

Many styles and variations have been made of the skull-and-crossbones Jolly Roger flag to create different pirate flags. It has been used by many pirates, including Christopher Condent, Black Sam Bellamy, and Edward England.

Without further ado, let’s take a look at some of the most famous pirate flags and their history.

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 richest pirates of all time. 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 own 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 your focus is on the number of captured ships, then Bartholomew Roberts beats him by a mile.

Also known as Black Bart, he took in 400 ships over his three-year career that took him from Brazil to Newfoundland to the Caribbean and Africa. During this period, Black Bart used multiple flags.

Black Bart was associated with the black flag with a white skeleton, a white pirate, and an hourglass between them. In historical pirate flags, he was the first to signal that the 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 vessel being attacked didn’t surrender.

His flag would eventually gain fame as the most iconic pirate flag in modern culture.

The Flag of Stede Bonnet

Bonnet was an English landowner who was wealthy before he turned to piracy in the 18th century. He often attached ships to the Atlantic Ocean and Caribbean Seas. He was often referred to as “The Gentleman Pirate” because of his previous status as a highly-ranking member of society.

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. It represented the scale of pirate justice.

The Flag of Edward Low

At the conclusion of 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 the anger and sheer evil of Low and his crew 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 accomplishment is 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. Even though Tew had only been a pirate for three years, he had amassed a wealth of approximately over 1 million dollars in today’s currency by the time that 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 has it 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 to indicate that he would be a slow, torturous death to all those who attacked him.

Raise Your Flag on Sunshine Scenic Tours’ Pirate Ship

Experience what Blackbeard, Henry Avery, or any of the 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 it’s like to sail on a pirate vessel.

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.

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