Top 7 Pirate Flags & The Tales of Their Captains
In celebration of this week's #InternationalFlagDay, I thought it appropriate to share a bit of insight to my favorite classic lore -- historical renowned pirates.
I’ve always loved history of the first buccaneers and pirate-turned privateers because the nature of their notoriety was oft based on legend, mystery and hearsay. Back then, it was common for a pirate to create a fear-mongering reputation across the high seas, because the intent was always to be able to capture a ship without a fight.
While there are a few notable battles that truly took place (we’ll go over a few), many pirates were not the disciplined sea rovers that famous fictions portray them as today. It was more common for a pirate to be inexperienced in battle, or fear the wrath of the tempestuous sea because he wouldn’t know how to swim.
The pirate flag was the first way to communicate a crew’s intent to a prey ship. Striking the colors of a nation’s flag, be it Spanish, English, French or Dutch was a typical tactic in luring prey ship into believing they were in safe and familiar company.
Here are a handful of common symbols used by the golden age pirate and what they stood for:
There are few accounts that if a ship were to surrender, the loot was seized and the ship left immobilized and abandoned like a bird with clipped wings. On the other hand, some of the crueler captains would still lead his men into malevolent antics, even if a prey crew surrendered for mercy. By 1964, privateers were ordered to fly a privateering red flag, commonly known as the “red jack”.
Pirates would seize the opportunity to then pose as trusted privateers. Soon after, black flags began to emerge to create the fearful distinction. The first noted black “Jolly Roger” was used by French pirate Emanuel Wynne as early as 1700. The design featured a skull and crossbones, paired with an hourglass to evoke urgency with the connotation that “time is running out” for their victims.
While the black flag has historically become a more iconic symbol for piracy, it all started with the red flag. It was later that the more feared and notorious captains would strike their own unique symbols to evoke a sure-fire surrender.
Here are some other common symbols used on pirate flags along with their most understood meaning:
Wings: Time is ‘flying away’. Often used as an alternative to the hourglass symbol.
Arm with Blade: Expect a tough fight.
Bleeding Heart: A slow and painful death awaits you.
Devil: Torment in imminent.
Skull and Crossbones: Death approaches.
A Dancing Man / Toasting a Drink: We aren’t afraid of dying.
Some noteworthy pirates used embellished variations of the above symbols, and while the black flag became increasingly common, some symbols remained red to maintain the message of “no mercy.” Here are a few of my favorite, most notable pirate flag designs and the captains that they represented...
(1659 - 1699)
A legend of the late 1600’s, Henry Avery was a man of many names. He is most recognized as the “successful pirate” due to his impressive efforts for a quick retirement with the comforts of his plundered riches. As for many pirates, little is known about his life before he took up his account.
Whole fleets would scatter at the sight of his flag, and Avery would tenaciously pursue until his violent ambition was met with surrender. His most famous capture was that of the “Gang-i-Sawai", which was part of Grand Moghul's of India convoy of ships. This capture is said to have resulted in a prize valued at about 600,000 pounds of plunder gold, silver and jewels. Each of Avery’s men was awarded 1,000 pounds -- worth at about 80 years of honest sea pays.
Avery later sailed to New Providence, bribing a local governor 7,000 pounds of treasure for his protection. When the Grand Moghul set out a bounty for his head with a generous prize of 500 pound, Avery is said to have changed his name to Benjamin Bridgman and fled to Ireland where he successfully vanished into obscurity. While his career as a pirate was short, it has been considered one of the more successful, since, unlike many, he survived his account and retired in the spoils of his exploits with no consequence.
Noted for his bravery and skill in battle, Edward England is most remembered as a man with “a great deal of good nature”. It was that very good-nature that would later become his demise. Notorious pirate-hunter Woodes Rogers would chase him out of the Caribbean, forcing him to sail to Africa to continue his plundering ways. In August 1720, England took to a sea battle that would end in a mutiny. After a several hour stalemate with East Indiaman, the Cassandra, England and his men successfully plundered approximately 75,000 pounds (amounting to tens of millions of dollars today). The beaten Captain James Macrae and his men were forced to flee to shore.
As the pirates pursued, but soon grew short of food and water. When Macrae gambled to surrender for mercy, England’s allowed them to walk free. His vengeful pirate crew was unpleased with his decision. So, England’s first-mate, John Taylor immediately organized a group of mutineers to remove him from power and maroon him on the island of Mauritius (off the coast of Madagascar). England would later find himself off the island with what little loyal crew members that stuck with him, where he made his way to St. Augustine's Bay, living out the rest if his days as a beggar.
‘Calico’ Jack Rackham
(1682 - 1720)
While Rackham wasn’t known for being a great fighter, or managing great wealth, he still is remembered as one of the most unique pirate legends from the Golden Age of piracy. He earned the alias of “Calico Jack” for the cheap and colorful calico clothing he was always known for wearing (rather than the silks and velvets that his counterparts would wear). Jack Rackham was more of a diplomat, as was never noted for being cruel, vengeful, or murderous. In fact, he’s remembered for going out of the way to treat his victims with restraint. Rackham was a small-time pirate that operated in the West Indies as quartermaster under the captaincy of Charles Vane (we’ll go into his story in a later blog).
In November 1718, Rackham became captain when Vane refused to attach a promising French man-of-war. Rackham put the decision up for a vote. The crew voted Rackham into captaincy and marooned Vane for his cowardice.
Sources are unsure of how it transpired, but Rackham would later earn a King’s Pardon in 1719 from Captain Woodes Rogers. It was around this time that Rackham would cross paths with Anne Bonny in New Providence, falling in love and taking her into his crew. Since she proved her fierce skill in battle, Rackham and the men let her walk the decks freely without disguise. The infamous Mary Read would also make her way into his crew, later walking freely as a woman after Bonny discovered her true gender.
Attended with two fierce women, Rackham continued to plunder the seas, quickly gaining a notoriety.
In October 1720, Rackham and his crew was bested by pirate-hunter Captain Charles Jonathan Barnet. As the story goes, the men were incapacitated with drink and hid below decks -- meanwhile Anne and Mary fought with bravery for their freedom, though were overpowered by Barnet’s privateer crew. Upon their trial in Jamaica, Read and Bonny were reprieved upon the discovery of their pregnancy. Though, Rackham and his men her hanged for their crimes of piracy. Calico Jack’s body was hung in an iron cage on the islet of Deadman’s Quary (near Port Royal) as a warning for future pirates.
Edward Teach ‘Blackbeard’
(1680 - 1718)
As the most feared and hated pirate of his time, Edward Teach is undoubtedly the most recognizable golden age pirate, even to this day. He was known for his massive beard, embellished with fiery woven rope when in battle to create the appearance of a demon from hell itself. He was a towering man with six flintlock pistols strapped to his person, striking fear to any adversary that may cross his way. While he was known for punishing crews that resisted his capture, Teach still wasn’t the most brutal of pirate captains. His demonic appearance did well enough to create his legacy across the seas.
In his early years of piracy, Teach began his life at sea as a privateer before taking up an account of piracy. He then sailed the seas with one Benjamin Hornigold, who would later retire with amnesty. Blackbeard would then transform his flagship into the renowned Queen Anne’s Revenge, boosting it with the firepower of 40 cannons. In May 1718, Blackbeard blockaded Charleston, holding several prominent citizens for ransom, and still managed to earn a pardon by governor Charles Eden.
Unsurprisingly, Blackbeard continued his account of piracy, carousing the seas with Captain Charles Vane. Blackbeard’s bloodiest battle was also his last. In November 1718, he was outnumbered by Royal Navy Lieutenant Robert Maynard and his men. Teach engaged in a hand-to-hand combat with Maynard, suffering five bullet wounds, and two dozen sword cuts before falling. Maynard would make an example of him as well, returning to Williamsburg with Teach’s head hanging at the bowsprit of his ship.
Bartholomew ‘Black Bart’ Roberts
Roberts is another figure that is best known for an incredibly successful career. In his short career of a little under 3 years, Roberts is noted to have captured over 400 vessels. Bartholomew was known for his dashing figure and was a devout Christian who forbade gambling among the ranks of his men. Don’t let his image fool you, for he also was remembered for killing troublesome crewmembers and inflicting torture on resistant victims. His life of piracy began when his captain, Howell Davis was killed in battle in 1719. Roberts was elected captain and became a reluctant pirate. His reasoning was “since he had dipped his hands in muddy water, and must be a pirate, it was better to be a commander than a common man.”
Soon, he would earn the alias of “Black Bart”. Roberts would lead his screaming men into battle with beating drums, quite literally striking fear into the hearts of his prey. Under the sails of his flagship, Royal Fortune, he would continue to capture over 100 ships, along with notably killing and hanging the governor of Martinique from the yardarm. Other devilish practices included cutting off the ears of his victims, or using them as target practice for his men
Though, his cruel reign came to an end in 1722, when he was killed by a broadside attack of grapeshot, fired by the HMS Swallow. His crew threw his body to the sea to keep him from being captured and defiled in a similar manner as other notorious pirate captains. The later surrendered after a 3-hour battle, resulting in the following: 54 hanging men, 37 sentenced to hard labour and 70 black pirates sold into slavery.
(1688 - 1718)
Often known as the “pirate gentleman” for his worldly background as an ex-army major, like Rackham, Bonnet was better known for his “not-so-pirate” ways. Historically, many believe that he became a pirate for no particular reason, crediting his change of lifestyle to boredom with the simple life.
Lacking experience of life at sea, Bonnet purchased his first pirate ship -- a measly sloop, Revenge complete with 10 cannons. He then hired his crew who would carry him into victory for his first several sea battles. Bonnet is also noted to have sailed alongside Edward Teach for some time, only to be convinced by his companion to abandon his leadership (because he was pretty useless as a captain.
While the advice would seem to be coming from the concern of a friend, Blackbeard would later dispatch one of his lieutenants to take control of the Revenge, where the crew accepted with no note of resistance. The trickery didn’t come with mercy, as Blackbeard would later steal all of Bonnet’s spoils, leaving him with the Revenge and 25 of his men. Bonnet vowed that he’d have his revenge. However, he would never have it, as in October 1718, pirate hunters would catch up to Bonnet, ensuing in a 5-hour battle that ended with Stede’s surrender. Bonnet tried to elude his fate to the very end, petitioning for forgiveness and attempting to escape his imprisonment (house-arrest in a private estate). Still, he was tried and hanged in November, along with 30 of his crew-mates.
(1690 - 1724)
Known as one of the more bloodthirsty of pirate captains, Low built his legacy with bloodshed. English government tenaciously pursued the sea criminal upon hearing word of his cruelties among own men and his victims. Coming from a destitute life of poverty, Low turned to piracy to earn his way.
During his voyage to the New World, Low would become a pirate captain when his shipmates organized to a mutiny against his pirate captain (name unknown). Low’s fame slowly rose as he captured and refitted his new flagship, The Fancy.
Stories of his violence spread across the sea, as he would often leave survivors to tell the tales of his victories, many describing him no less than a psychopath. Low’s torments included burning alive, chaining, mutilating and even forcing his captives to eat the heart of their captain.
Horrified by his acts of violence, British authorities dispatched a force to capture him in 1723. Many historians are uncertain of the details of his ending. Though several sources suggest that the French captured Low, immediately bringing him to his end with a quick hanging with no trial. Some sources suggest that he managed to escape and fled into hiding in Brazil for the rest of his days.
These tales only scratch the surface of pirate lore.
There are several others who made their name in their exploits as scourge of the sea, still these captains were not only most notorious for their acts, but for their “calling card” symbols used to startle victims into surrender. The best of pirates were often considered as those who would plunder without the need to go into battle.
Which captain captured your intrigue the most? Which flag do you fancy most? Leave your thoughts in the comments below and stay tuned for more pirate lore upon the horizon!
Stay tuned for a special reveal of the flag design of original character Silver Sallie, from my upcoming historical fantasy thriller fiction series,
The Black Tide Chronicles!
Fair winds and following seas --
the romantic rover.