Walk into any seaside gift shop from Key West to Nassau and you'll see it. A black flag featuring a skull centered between two crossed cutlasses. It's sleek. It's aggressive. Usually, the tag on the plastic sleeve identifies it as the Anne Bonny pirate flag. People buy them for boat decks, dorm rooms, and historical reenactments, fully convinced they are flying the colors of the most famous woman to ever prowl the Caribbean.
There's just one problem. It probably isn't hers.
History is messy. While we love a clean narrative with branded logos for our favorite historical anti-heroes, the Golden Age of Piracy didn't work like a modern franchise. Anne Bonny was real, her trial is a matter of public record, and her "theatrical" behavior on the deck of the William is documented by eye-witnesses. But the specific flag design we attribute to her today? That's a bit of a historical ghost.
The Mystery Behind the Cutlass Design
Most of us recognize the "Jolly Roger" as a skull and crossbones. That's the classic. However, the specific variation with the swords—often called the "Calico Jack" flag—is the one most frequently sold as the Anne Bonny pirate flag. This makes some sense on the surface. Anne Bonny sailed under John "Calico Jack" Rackham. They were lovers, partners in crime, and eventually, co-defendants.
Since she was a core member of his crew, his flag was, by extension, her flag.
But if we look at the primary sources, specifically A General History of the Pyrates published in 1724 by Captain Charles Johnson (a pseudonym likely belonging to Daniel Defoe or Nathaniel Mist), the details get blurry. The book mentions Rackham’s flag having "two pieces of white taffety in the shape of a skull and crossbones," but it doesn't explicitly mention the cutlasses in the earliest descriptions. The swords likely became associated with the flag later to distinguish Rackham's brand from the more generic designs used by Edward England or Blackbeard.
Why does everyone call it the Anne Bonny flag now? Honestly, it’s mostly marketing.
In the late 20th century, as interest in female pirates spiked, historians and hobbyists needed a visual shorthand for her. Because she was famous for her skill with a blade—witnesses at her trial specifically mentioned her wielding a machete and a pistol—the "crossed cutlass" design felt right. It fit her "brand."
What Did Anne Bonny Actually Sail Under?
If you were standing on the deck of a merchant sloop in 1720 and saw a ship approaching on the horizon, you wouldn't be looking for a specific "Anne Bonny" logo. You’d be looking for the "Black Flag."
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Pirates used flags as a form of psychological warfare. It was a communication tool, not a fashion statement. Most crews carried a variety of flags, including "false colors" (the flags of friendly nations like England or Spain) to trick victims into letting them get close. Once the pirate ship was within striking distance, they would hoist the "Jolly Roger."
The message was simple: Surrender now, and we might let you live.
If the victim refused, the pirates would sometimes hoist a "Bloody Flag"—a solid red banner. That meant "no quarter." No mercy. Everyone dies.
Anne Bonny’s actual experience with flags was utilitarian. When she, Mary Read, and Calico Jack stole the William from Nassau harbor, they weren't worried about graphic design. They were worried about speed. The Anne Bonny pirate flag they flew was the one that belonged to the ship’s captain, Rackham.
The Trial Evidence
We have the transcripts from the trial of Anne Bonny and Mary Read held in Jamaica in late 1720. They are fascinating. Witnesses like Dorothy Thomas, who was taken by the pirates, testified that the women wore "long jackets, and long trousers, and handkerchiefs tied about their heads" and that they were "very active on board."
The witnesses mentioned the weapons. They mentioned the cursing. They mentioned the courage of the women compared to the "cowardice" of the men during the final capture.
They did not mention a specific, unique flag for Anne.
In the eyes of the law, the flag was evidence of "piracy on the high seas." It didn't matter if it had bones, swords, or an hourglass on it. The act of flying a non-national flag while attacking a vessel was the crime.
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Why the Myth of the Flag Persists
Humans love symbols. We want to believe that Anne Bonny had a specific identity that she projected to the world. The idea of a woman in the 18th century rejecting societal norms, donning men's clothing, and flying a flag of rebellion is incredibly powerful.
The cutlass flag has become a symbol of female empowerment and subversion. It represents the idea that Anne was not just a passenger or a "pirate's girlfriend," but a combatant in her own right.
And she was.
Even if she didn't sit down with a needle and thread to sew a specific design, the black flag with the crossed blades captures her spirit. It’s the visual version of her famous quote to the imprisoned Rackham before his execution: "If you had fought like a man, you need not have been hang'd like a dog."
How to Spot a "Fake" Historical Flag
If you’re a history buff or a collector looking for an authentic representation of an Anne Bonny pirate flag, you have to accept a certain level of ambiguity.
Most "authentic" pirate flags from that era didn't look like the crisp, screen-printed versions we see today. They were handmade. The skulls (or "Death's Heads") were often crude and anatomically incorrect. Sometimes they looked more like weird aliens than humans.
- Fabric: Authentic flags were usually made of wool or silk (taffeta). Polyester didn't exist.
- Color: While black was the standard, "blood red" was just as common and significantly more terrifying to 18th-century sailors.
- Size: These weren't small. To be seen from miles away, flags were often 6 to 10 feet long.
- Design: Symbols often included skeletons holding spears, hearts dripping blood, or hourglasses (to show the victim their time was running out).
The crossed cutlass design is historically "plausible" for the Rackham crew, but it’s more of a 20th-century consensus than an 18th-century fact.
The Cultural Impact of the Banner
Today, the flag is more popular than ever thanks to shows like Black Sails and various pirate-themed video games. In these fictionalized accounts, the flag is often used to give Anne her own agency. It separates her from the male pirates.
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In the gaming world, the Anne Bonny pirate flag is often a "skin" or an unlockable item. It’s a way for players to signal that they value the history of female pirates. This digital afterlife has solidified the cutlass design as "hers" in the collective consciousness, regardless of what the dry dusty archives in Jamaica say.
It's a weird quirk of history. Sometimes the myth becomes more "real" than the truth because the myth serves a purpose. The cutlass flag tells a story of defiance that a plain black cloth just can't match.
Actual Steps for Historical Accuracy
If you are writing about this, teaching a class, or just want to be the smartest person at the Renaissance fair, here is how to handle the topic of the Anne Bonny pirate flag accurately:
- Acknowledge the Source: Explain that the "Calico Jack" flag (skull and crossed cutlasses) is the one associated with her because of her partnership with John Rackham.
- Clarify the Ownership: Make it clear that there is no evidence Anne Bonny had a personal, unique flag separate from the ship she served on.
- Highlight the Weapons: Focus on the cutlasses. While the flag's design is debated, her use of the weapon is not. She was a documented combatant who used blades and pistols effectively.
- Differentiate the "Jolly Roger": Note that "Jolly Roger" was a generic term for any pirate flag, and different captains had different motifs.
- Contextualize the "Bloody Red": Remind people that a red flag was actually scarier than a black one. If Anne saw a red flag, she knew a fight to the death was coming.
The real story of Anne Bonny is wild enough without needing to invent a graphic design career for her. She was a woman who escaped a stifling marriage, dressed as a man, fought off navy boarding parties, and vanished from history after her pregnancy saved her from the gallows.
Whether she sailed under a skull, a sword, or a plain black sheet, her legacy of rebellion is what actually carries the weight. The flag is just the souvenir we take home to remind us that she was there.
To truly understand the era, you should look into the High Court of Admiralty records from 1720. They provide the most "unfiltered" look at what the crew was actually doing day-to-day. You’ll find that their lives were less about cool logos and more about the grueling reality of maritime theft and the constant threat of the "hempen jig" (the noose).
If you want to represent her correctly, don't just fly the flag. Tell the story of the trial. Tell the story of the William. And definitely mention the "pleading the belly" legal maneuver that kept her alive when all the men around her were swinging from ropes.
Next Steps for Research
- Primary Source Reading: Search for a digitized copy of The Tryals of Captain John Rackam and Other Pirates (1721). It is the most accurate account of the events leading to the capture of Bonny and Read.
- Museum Archives: Check the online database of the National Maritime Museum in Greenwich. They have some of the few remaining fragments of authentic 18th-century maritime flags.
- Visual Analysis: Compare the "Rackham" flag to the flag of Thomas Tew or Henry Every. You'll notice how the "skull and crossbones" evolved from a generic symbol of death into a specialized branding tool for different crews.