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The real pirates behind Our Flag Means Death

If you've watched the first season of this HBO Max series, you may have accidentally learned something about real pirate history.

Image credit: Our Flag Means Death

Our Flag Means Death holds a special place in our hearts among the suite of yet-uncanceled or unlisted HBO Max original programming. A rarity among cult hit shows these days, there’s no series of comics or films or video games for us to pick apart and analyze to understand background and context. Our Flag Means Death is a show that stands all on its own thanks to smartly written comedy, emotionally resonant romance, impeccable stunt casting, and some unbeatable needle drops.

All the same, that’s not to say the show comes wholecloth from nothing. There’s still one hot pre-existing IP that this misadventure on the high seas happens to draw upon: actual world history and figures long dead. Any similarities to these persons, to paraphrase a repeated legal warning, are not purely coincidental.

The more you look into the Golden Age of Piracy in the early 18th century, the more you may be surprised about how much the show gets right about the people involved. How much exactly? Well… it’s not perfect. We’d say somewhere between The Great and Chernobyl. Still, if you thought coming into this that Blackbeard was the only pirate to sail the seas in our world and in this one, then allow us to lift the bilge from your eyes. Here we’ve collected the dramatis personae of Our Flag Means Death and their clear analogs to the pirates of the Caribbean Sea.

Stede Bonnet

Stede Bonnet
Image credit: HBO Max

Yes, he was a real guy. Born in 1688, Stede Bonnet was an educated Englishman with a wife and children who left his family behind for a life of misadventure on the high seas as “The Gentleman Pirate,” despite no prior knowledge of piracy or life at sea. Rather than steal a ship, as pirates usually do by definition, Bonnet used his own money to have The Revenge built himself. He hired a crew. He paid them wages. And he even joined his crew to Blackbeard’s from 1717 to 1718, until Blackbeard assumed complete command, beached his crew, and made off with The Revenge and all of their property. From there, Bonnet briefly took an offer from the king to work as a privateer, a post he abandoned to return to piracy and rescue his men that Blackbeard had left marooned.

And that’s… a pretty accurate summary of Our Flag Means Death Season 1, honestly. Minus some smooching. Well, if we can rely on history to dictate what’s in store for Stede in Season 2, then Stede Bonnet will go on to start a sham trading business until getting back to full piracy again, get battered about by some nasty hurricanes, wage his final battle against Colonel William Rhett at Cape Fear River, be sentenced to hanging, and never see Blackbeard again. Personally, we’ll be fine if they take a few liberties here.

Edward "Blackbeard" Teach

Image credit: HBO Max

He’s… are you serious? He’s Blackbeard. Like, the pirate Blackbeard. You know this. I don’t have to tell you Blackbeard was real. I mean, if you’ve heard of pirates, you’ve heard of Blackbeard. Should we even do this one? There are plenty of books and movies out there about Blackbeard. He’s in One Piece. Maybe don’t watch One Piece to learn about Blackbeard. All right, quick overview.

First of all, all the stuff about Blackbeard being “The Kraken” was made up for the show. The kraken myth was pretty hazy at the time Blackbeard was active, and only came into popularity decades afterwards. Any record of Edward Teach’s life before he became a pirate has been lost to time. Edward Teach might not have even been his real name. So if someone tries to sell you a Blackbeard origin story, they’re making it up. But from 1716 to 1718, Blackbeard was the terror of the West Indies. Teach commandeered a French slave ship and renamed it the Queen Anne’s Revenge, amassing over 40 cannons and a crew of 300 men. His love of “fuckery,” as noted in the show, is well-documented, lighting fuses in his hat to strike fear into his victims and enemies. Blackbeard eventually accepted a royal pardon to privateer for the king but was soon back at sea, a turn of events told its own way in season one. Blackbeard was killed in 1718 by British lieutenant Robert Maynard of the Royal Navy, so hoist the red flags if that name comes up.

Israel "Izzy" Hands

Izzy Hands
Image credit: HBO Max

Captain Blackbeard’s crew in Our Flag Means Death has mostly been fictitious so far, with one notable exception: You might know the name Israel Hands as belonging to Long John Silver’s first mate in Treasure Island, but both Robert Louis Stevenson and Our Flag Means Death have been pulling from the same source: “Izzy” was also Blackbeard’s first mate in real life. When Blackbeard captured an enemy ship at sea, it was often Hands who commandeered the vessel until they returned to shore to gather their stolen bounty. When Blackbeard got into trouble, whether that was martial forces at sea or running his ship aground, it was Hands who was there to bail him out.

Despite that loyalty and dedication, Hands was rewarded for his efforts with a permanent injury to his knee when Blackbeard fired his gun at another crewmate, missed, and struck Hands instead. (Honestly, keep an eye out for that happening eventually on the show. That’s too good a bit for them not to crib.)

Although Hands was eventually captured along with the rest of Blackbeard’s crew, he earned himself a pardon by giving up the corrupt government officials in colonial North Carolina with whom Blackbeard had consorted. He’s reported to have died a beggar in London – a poor fate, but a better one than most of his peers.

Calico Jack

Calico Jack
Image credit: HBO Max

Maybe the real Calico Jack, as played by Will Arnett in Our Flag Means Death, was also the GOB Bluth of the sea. There’s no way to know for sure. But John Rackham, nicknamed “Calico Jack” for his unbleached cotton wardrobe, was very much a real pirate. Despitre their shared history in the series and being active pirates on the same seas at the same time, we don’t have any record whether Jack and Blackbeard had ever even met each other. I don’t know if you’ve seen it, but the ocean is pretty big.

Calico Jack first earned his crew after a mutiny against his own captain, Charles Vane, whom Jack branded a coward for failing to pursue a French man-of-war twice their ship’s size. Despite the complaints of his leadership campaign, Jack played it fairly safe as a captain himself at first, sticking close to shore and boarding small ships for easy pickings. But as time went on, Calico Jack grew bolder. He was eventually caught by the militia of Governor Wodes Rogers of the Bahamas, but Jack escaped his sentence by taking advantage of Rogers’ known enmity for his old Captain Vane – claiming that Vane had forced Jack’s crew into piracy.

It was around this time ashore that Calico Jack met Anne Bonny, one of the most infamous women in pirate history. Anne was the wife of James Bonny, one of Governor Rogers’ sailors, and Jack offered to buy Bonny out of her marriage when their affair was discovered. James refused, so Bonny left with Jack’s crew without divorce papers and they stole a new sloop for a life of crime on the high seas. Together, Jack and Bonny rebuilt their crew, their wealth, and their infamy, until Governor Rogers caught up with them and sentenced Jack to hanging in 1720.

Spanish Jackie

Spanish Jackie, as played by Leslie Jones in Our Flag Means Death with her jar of noses and penchant for speaking in third person, certainly cuts an imposing and memorable figure. But the legend which precedes her suggest that she may be intended to be a depiction of Jacquotte Delahaye, another notorious female pirate of the era. Here’s the thing, though: nobody can really say whether Jacquotte Delahaye ever really existed. Most of the written accounts of her exploits come from French fiction writer Leon Trench as late as the 1940s, and any stories of her or attributed to her before then may be apocryphal. Delahaye's story is one filled with romance and drama, which would seen dubious on its own if not for the many similarly fantastic accounts of the pirates who would have been her contemporaries.

According to legend, Jacquotte Delahaye was born to a French woman (who later died birthing her brother) and a Hatian man (who was murdered in Delahaye's youth). Assumed dead and with nowhere else to go, Jacquotte dressed as a man and took to the sea, fighting great battles and winning hundreds of followers until conquering the Caribbean island of Tortuga from Spanish rule, where she established a republic and haven for piracy. It’s quite fitting that we see Bonnet and company accepting her hospitality. Whether real or not, however, her prodigious number of husbands she appears to have in Our Flag Means Death are an entirely new addition to the legend – drawing, perhaps, on a gender-reversed legend of the many-wived Bluebeard.

Jim Jimenez

Image credit: Our Flag Means Death

All right, as far as we know, there’s never been a deadly nonbinary knife-throwing pirate who was raised by nuns to avenge their family. But the story of Jim is still familiar to students of pirate history, harkening back to a real historical figure who was perhaps just as interesting: Mary “Mark” Read, an English pirate who terrorized the West Indies through the late 1710s. Read began presenting as male at a young age, first to claim her family inheritance and then to join the military. While serving, she met a Flemish soldier to whom she revealed her identity, and the two married.

Read’s husband died shortly after, however, so Read rejoined the military in the guise of Mark Read. On the way to the Netherlands, Read’s ship was boarded by pirates, an encounter she survived by agreeing to join their crew. That crew was captured, privateered, and then mutinied against their captain under the King’s flag to sail as pirates once more. That was about the time Read met Calico Jack and Anne Bonny, who was also presenting as a man to get along with their own pirate crew.

Unbelievably, but all true according to 1724’s A General History of the Pyrates by Charles Johnson, Bonny and Read fell in love with each other, and Bonny revealed her identity as a woman to her new companion. Read returned that revelation with one of her own. Read would reveal her identity one more time that we know of: after Calico Jack’s crew was captured in 1720, Bonny and Read both claimed pregnancy to avoid the hangman’s noose. Read died in prison the next year, but passed on into legend.

With Jim separated from the rest of the crew, maybe Season 2 is when we get to meet the Our Flag Means Death take on Anne Bonny. But with the surprising amount of pirate history incorporated into Season 1, we’re anticipating a few more familiar faces in our next voyage out to sea.

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