Who Are Stede Bonnet and Blackbeard? OUR FLAG MEANS DEATH’s Real Pirates, Explained

Two of our favorite Kiwi comics are reuniting for one of the silliest projects we’ve heard of in a while. Rhys Darby stars in the Taika Waititi comedy series Our Flag Means Death. The HBO Max show follows the extremely-inexperienced pirate Stede Bonnet (Darby), who decides to abandon his life as a wealthy Englishman in Barbados for a life of the seas. Our Flag Means Death promises an extremely loose adaptation of the Gentleman Pirate’s life and sea travails. But, obviously, the show’s Stede Bonnet and the notorious Captain Blackbeard (Waititi) are based on actual historical figures. Here’s what you need to know about the real-life pirates behind the Our Flag Means Death

Rhys Darby wears his fancy green captain suit on his ship in Our Flag Means Death

Stede Bonnet, the Gentleman Pirate: Who Was Stede Bonnet // Stede Bonnet’s Transformation Into a Pirate // How Stede Bonnet Got Named “the Gentleman Pirate” // Stede Bonnet’s Downfall and Death // Stede Bonnet in the Media and Pop Culture

Edward “Blackbeard” Teach: Who Was Blackbeard? // The Early Days of Blackbeard and His Rise to Legendary Pirate Fame // Blackbeard’s Grisly Death // Blackbeard’s Ship and Flag // Film and Television’s Many Depictions of Blackbeard // Blackbeard in Other Pop Culture and Media

Stede Bonnet, the Gentleman Pirate 

Who was Stede Bonnet?
The top of Rhys Darby's head popping up on Our Flag Means Death

By all accounts, Bonnet was not born into a life of piracy.  Stede Bonnet was born in the late 16th century to an English family in Barbados. Bonnet’s family owned and operated a 400-acre sugar plantation. His parents died not long after he was born, leaving Bonnet, his siblings, and the estate he’s inherited in the hands of guardians. (Guardians who, according to the North Carolina Historical Society, ensured his well-educated upbringing.)

For a while there, it seemed like Stede Bonnet was living the life expected of someone in his respectable position. He was married with a trio of children. He even held the rank of Major in the local militia. But by summer 1717, Bonnet abandoned his cushy life and family for piracy.

Stede Bonnet’s Transformation Into a Pirate
A stede bonnet etching
A General History of the Pyrates

Notably, Bonnet had exactly zero experience on the seas before pivoting to piracy. This, of course, makes his turn to professional criminality all the more curious. Historians aren’t exactly positive about why Stede Bonnet chose to become a pirate. Taking on a life of piracy meant leaving his family and comfortable existence for a profession he had no experience in. Not to mention, Stede Bonnet’s decision to turn to piracy held the promise of a noose should he ever get caught. The reason cited most often is the unkind “nagging wife” excuse.

But historian Colin Woodward suggested to Smithsonian Mag a combination of factors drove Bonnet to become the Gentleman Pirate. Some of the reasons cited include his tumultuous family life after his child’s passing and a desire to rebel against England’s King George I. (Woodward alleges Bonnet was a supporter of the exiled Scottish King, James I.)

How Stede Bonnet Got Named “the Gentleman Pirate”
Rhys Darby has a dagger under his nose on Our Flag Means Death

But why is Stede Bonnet called “the Gentleman Pirate”? This moniker has everything to do with Bonnet’s unorthodox turn to piracy by way of ditching his posh life for the gritty seas. For starters, Stede Bonnet outright legally purchased his ship, which was named the Revenge, a far cry from the usual way—stealing. Even the ship’s name was the 18th-century pirate equivalent to naming your dog, Max. But we can start to see how Stede Bonnet’s real pirate history may inform Our Flag Means Death. The interested should note a skull flag with a horizontal long bone, heart, and dagger is commonly attributed to Stebe Bonnet. However, what Bonnet’s flag looked like exactly remains lost to time. 

Still, after securing his ship and crew, Bonnet and the Revenge scoured the East Coast and found success there. He seized several boats before making his way back down to the Caribbean. There Stede Bonnet first crossed paths with Blackbeard. The pair worked together in late 1717. After initially parting ways, Blackbeard and Bonnet became reacquainted just months later. Though Bonnet admired the revered pirate Blackbeard, their second meeting was a bit more complicated. Blackbeard more or less took over the command of Revenge from Stede Bonnet, deeming him to lead a pirate crew. Despite that humiliating setback, Bonnet resumed his pirate ways in the summer of 1718. But to preserve a pardon he allegedly obtained from North Carolina’s governor, Stede Bonnet changed his ship’s name to the Royal James and took on an alias. 

Stede Bonnet’s Downfall and Death
Pirate Flag for Stede Bonnet Death section
Wikimedia Commons

Bonnet’s reign upon the seas lasted about 15 months. In late summer 1718, Bonnet and the Royal James returned to Cape Fear, North Carolina, with their loot for repairs after sailing up and down the East Coast. A hotbed for piracy, the governor of South Carolina, hearing the Gentleman Pirate was sailing his waters, sent Colonel William Rhett after Bonnet and his crew. 

In late August, Rhett forced Bonnet and his crew to surrender. While Bonnet briefly escaped custody, he didn’t get far.  On November 12, 1718, Bonnet and his crew faced trial for piracy (The transcript of the trial, which is available to read in full, is downright fascinating.) While he made a second go for a pardon—he was a gentleman after all—it was to no avail; the government did not grant Stede Bonnet a second pardon.  Bonnet was hanged and ultimately died on December 10, 1718, in Charleston, South Carolina’s White Point Garden. Still, he managed to outlive Blackbeard. Stede Bonnet even went down in history as a good and revered pirate, though his reputation at sea is more than a little odd. And, of course, ripe for satire.

Stede Bonnet in the Media and Pop Culture
Stede Bonnet in Assassin's Creed IV: Black Flag

While certainly not one of the most feared or famous pirates of all time, Stede Bonnet’s eclectic road to piracy—and his legendary nickname—lends a certain notoriety of its own. Meaning, of course, he pops up from time to time in pirate-related media. Bonnet plays a supporting role in Assassin’s Creed IV: Black Flag. Alongside the likes of “Calico Jack” Rackham, Anne Bonny, and Blackbeard, Bonnet is one of many famous pirates that appear in Assassin’s Creed IV.  The protagonist Edward Kenway, a former privateer, encounters him on his journeys. 

Most recently, the villainous pirate Stephen Bonnet appears in season four of Outlander. Many often wonder is Stephen Bonnet really Stede Bonnet? But the fictional character isn’t explicitly based on Stede Bonnet. This feels especially apparent when we consider their widely differing backstories. (Outlander‘s Stephen Bonnet hails from Ireland and grew up aboard ships, something the real Stede Bonnet would not understand.) Outlander season four also takes place in 1767 South Carolina—several decades after Stede’s death. It’s likely though that Diana Gabaldon, who wrote the novels, drew direct connections to the Gentleman Pirate as an homage to the Golden Age of Piracy.

Of course, we will soon see Stede Bonnet take center stage among Our Flag Means Death‘s pirates.

Edward “Blackbeard” Teach

Who Was Blackbeard?

A profile of Taika Waititi and his beard in Our Flag Means Death

The name Blackbeard is more or less synonymous with piracy… Much more so than Stede Bonnet’s. As one of the most prolific and feared pirates to ever sail the seas, Captain Blackbeard often feels more like a legendary figure than a real person. (Though Blackbeard was very much real.) As such, so much about his life before piracy remains shrouded in mystery. 

As one of the most notorious pirates of the era, Blackbeard’s given name is likely a pseudonym. Although, like everything else about the pirate’s early life, Blackbeard’s real name is up for debate. But, more or less, people know Blackbeard as Edward Teach—or a close variation such as Edward Thatch and the like. By most accounts, Blackbeard was born in Bristol, England, sometime towards the late 17th century before making his way over to live in Jamaica. In the Caribbean, Blackbeard became acquainted with the seas and the pirate life. Blackbeard got his start as either a British privateer or in the Royal Navy.

The Early Days of Blackbeard and His Rise to Legendary Pirate Fame
Etching of Blackbeard from A General History of the Pyrates
A General History of the Pyrates

A lot of what we know about Blackbeard stems from A General History of the Pyrates. This 1724 account of several major pirates comes to us written by Captain Charles Johnson. (Though Johnson’s actual identity is also disputed. Most agree Johnson is a pen name. And many believe Daniel Defoe actually authored the history.) According to General History, Blackbeard spent his early pirate days, beginning in late 1716, under the tutelage of Benjamin Hornigold. Hornigold eventually gave the budding pirate his own sloop to man before retiring soon after.

In just a short time at the center of his own pirating operation, Blackbeard was incredibly successful, raiding ships and towns alike. One of Blackbeard’s most famous ventures involved creating a blockade around Charleston harbor in 1718, seizing ships and their crews and holding them for ransom. This ransom was eventually met after about a week. Due to his demands involving medicine, many believe Blackbeard was likely suffering from Syphilis—which is a supremely tough break for the pirate as his requested medicine probably didn’t work on his illness. He also finagled a deal with the governor of North Carolina. Blackbeard secured a pardon under the guise of retirement. But, of course, that doesn’t last long.

Blackbeard’s Grisly Death 
Blackbeard's head hanging after his death
Wikimedia Commons

But like a pirating Icarus, Blackbeard flew a little too close to the sun with his brazen activities. Eventually, Virginia’s governor, Alexander Spotswood, had enough of Blackbeard and his crew terrorizing the coast. And thus, he gathered a crew commanded by Robert Maynard to track down the pirate and end his reign on the water.

In November 1718, Maynard and his fleet cornered Blackbeard and his men in Ocracoke Island. There, they engaged in a bloody battle—during which Blackbeard and his crew fell to Maynard. Allegedly, the notorious pirate captain sustained five gunshot wounds and more than 20 stab wounds before he died at the British Royal Navy’s hands. Some accounts, including General History of the Pyrates, state that Blackbeard was beheaded after death. Instead of a grave, his head got stuck up as a warning to pirates of the fate awaiting them. In all, Blackbeard was a pirate for just about two years. But he still managed to cultivate a legendary, if notoriously evil, reputation. (A reputation of spreading fear and villainy that some scholars now dispute.)

Blackbeard’s Ship and Flag
An artist Rendering of Blackbeard's Flag
Royal Museums Greenwich

Blackbeard used a few different ships during his tenure plundering the seas between the West Indies and the East Coast of North America. But Blackbeard’s flagship vessel was the  Queen Anne’s Revenge. The ship, which he commandeered from French privateers, was allegedly originally a British merchant ship from, ironically, Bristol. The Queen Anne’s Revenge appears to have sunk off the coast of North Carolina. The remains of Blackbeard’s ship were recently discovered near the town of Beaufort. 

Like everything else about Blackbeard, his flag lives on in infamy—even if its validity is up for dispute. Unlike the other Jolly Roger flags in history, Blackbeard’s is a bit grisly. It feels devilish, like the man whose ships bore it. It depicts a horned Devil pointing a spear towards a red heart, with a glass in the other hand. According to the Maritime Museum Greenwich, Blackbeard’s flag suggested an “alliance with the Devil.” Definitely a proper intimidation tactic for the vessels he was about to seize. And probably something Stede Bonnet would have co-signed as true. 

Film and Television’s Many Depictions of Blackbeard
Ian McShane in Pirates of the Caribbean: On Stranger Tides
Walt Disney Studios

As the ultimate figure of piracy’s Golden Age, Blackbeard is a mainstay in pirate-related media—both fiction and non-fiction. Whether explicitly or as an inspiration for a fictional character, Blackbeard often appears across pop-culture’s movies and TV shows. It’s too overwhelming to detail every single time we’ve seen Blackbeard on our screens, in our books, and our blackened evil hearts—but here’s a small smattering.

Naturally, Blackbeard’s anchored several documentaries, films, and TV series, including a 1952 RKO Radio Pictures film, 2005 BBC miniseries, and a short-lived 2014 NBC series. Ray Stevenson plays Blackbeard in seasons three and four of the TV series Black Sails. The Starz series serves as a prequel to Robert Louis Stevenson’s seminal pirate novel, Treasure Island. As such, it features the fictional Walrus crew on their ventures through the Caribbean and their encounters with their real-life contemporaries. 

Interestingly, Blackbeard doesn’t appear until the fourth installment in the Pirates of the Caribbean franchise, On Stranger Tides. In the film, Blackbeard, played by Ian McShane, survived his recorded 1718 death during battle at Ocracoke Island to make life difficult for Jack Sparrow. (Notably, it’s through a very Pirates-appropriate bit of mysticism that he lived.) 

Additionally, Blackbeard has also wormed his way into another famous pirate’s story—Captain Hook. In Once Upon a Time and the 2015 Pan, he’s depicted as a rival to Captain Hook. (Hook, in both cases, has a bit of an image rehab as less cartoonish villain and more roguish and morally dubious.) Hopefully Stede Bonnet doesn’t feel too jealous about it. 

Blackbeard in Other Pop Culture and Media
Taika Waititi and Rhys Darby drink tea on Our Flag Means Death

Like Stede Bonnet, Blackbeard also appears in a supporting role in the video again, Assassin’s Creed IV: Black Flag. He shows up numerous times throughout the game to aid Edward Kenway, his infamous violent demeanor more of a front for a kinder, tactical pirate. He’s even a character in a beloved pirate manga. Blackbeard appears in One Piece, which follows a young pirate, Monkey D. Luffy, and his crew on their quest to become the next King of the Pirates. The title refers to the ultimate treasure that’ll help them meet their goal. Marshall D. Teach a.k.a. Blackbeard—named for the infamous pirate—is one of their most notable foes. 

Stede Bonnet and Blackbeard: Our Flag Means Death‘s Real-Life Pirate Inspirations

How much of Stede Bonnet and Blackbeard’s pirate histories Our Flag Means Death will use remains to be seen. The series will have 10 episodes in its first season. But if its terrific cast, including Taika Waititi, Rhys Darby, and more has anything to say about it, we hope we’ll see news of Our Flag Means Death season two soon. And hopefully, we’ll get to see some of these fascinating facts from the past come to life. Blackbeard’s roguish life and Bonnet’s gentlemanly ways seem ripe for a deep exploration. And who knows maybe Our Flag Means Death could even add more famous pirates to the mix. Plus, who doesn’t love a pirate bromance? We know we do.

Our Flag Means Death released on March 3, 2022. It currently streams on HBO Max.

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