Black Sails: A Look at Fictional and Historical Pirates

We break down the literary and historical pirates who terrorize the high seas on Black Sails!

Black Sails season 3 premieres on Starz on January 23rd. If you want to catch up on seasons 1 and 2, click here!

This article contains some Black Sails spoilers.

Black Sails has placed itself at an interesting junction between fact and fiction, bringing the pirates of Robert Lewis Stevenson’s Treasure Island to live in the real-world pirate city of New Providence, Nassau, during the Golden Age of Piracy.

What this means to you, the viewers, is that most of the characters have a “real history” apart from the show. Some of these histories run closely parallel to the characters you see on your television. Let’s take a look at some of them.

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Black Sails: Pirates of Treasure Island


Pirate captain, former gentleman, a schemer, Captain Flint (his given name is never revealed) is one of the most striking characters in Treasure Island, even though he never actually appears in the book. Flint is the man who captured and buried the treasure, marking its location with the pointing limbs of murdered shipmates.

Flint’s ultimate end? Death by liver failure in a cheap rooming house in Savanah. His former crew remember the days when they sailed with Flint with nostalgia and terror.


A legendary schemer, Silver is the one-legged pirate who moves the action in Treasure Island. He already owns a successful business, the Spyglass tavern, but he wants it all: fortune, fame, and the kind of power that comes when you’ve got cash to burn. He signs his former shipmates aboard the ship Hispaniola, plans the mutiny, carries it out, and is only foiled by the actions of teenage Jim Hawkins.

Revealing how Silver got to be this cunning, strong, daring leader is half of what drives Black Sails. As Stevens said, “Men feared Flint, but Flint feared Silver.”

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Billy Bones

Treasure Island starts when Billy Bones blows into town, with a mind full of horrible memories and a chest full of treasure. It is Bones who sings “Yo ho ho and a bottle of rum!” – The first time anyone ever did.

Billy wants the local folk to call him “Captain” and he tells tales of horrible doings, then wakes at night from recollections too terrible to reveal. He’s the man who stuck with Flint when all else left him, and he’s the one who gets the treasure map for his trouble.


Barely mentioned by Robert Louis Stevenson, Max (un-named in the book) is Silver’s wife, a “negress” of uncommon intelligence, who is supposed to sell their tavern and rendezvous with Silver in the Caribbean after he secures Flint’s treasure.

Flint does make off with some of the treasure, and I’ll assume he meets Max again, and they have further adventures.

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Black Sails Historical Pirates


Like many pirates, Charles Vane’s origins are obscure. He was definitely one of the captains that founded the Pirate Republic on Nassau, but he does not seem to have been well-liked, even by the pirates (and he definitely didn’t run around shirtless and in tight black leather pants… Sorry ladies!).

He was captain of the Ranger, but was deposed by Calico Jack when he refused to attack a heavily armed French ship. Given one of the flotilla’s smaller sloops when he lost the Ranger to Rackham, Vane tried to re-build his power, but was shipwrecked and ultimately hanged. Vane is also noted for standing up to the English authorities, and refusing to accept a pardon from the King.

Calico Jack Rackham

A contemporary picture shows a gaunt-faced, hook nosed man. Rackham was brave to the point of being foolhardy. He was quartermaster of Vane’s Ranger and after becoming captain, he was one of those who accepted a pardon for his piratical acts.

Rackham’s downfall was Anne Bonny. He wanted to marry her, and when he could not do so (she was already married and they could not get permission from her husband) he went back to sea and took her with him, apparently planning on taking revenge on the world.

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Jack cut a wide swath of mayhem through the Caribbean, but was caught when he celebrated too soon after escaping a Navy cutter. He and the crew were dead drunk when the Navy found them again, and they were unable to fight.

Rackham was hanged in Jamaica on March 29, 1721.

[related article – Black Sails: The Real Story of Jack Rackham and Anne Bonny]

Anne Bonny

Anne came from a well-to-do family, and married the small-time pirate James Bonny in a fit of teenage rebellion. Bonny was infuriated that Anne’s father cut her off without a penny. He mistreated his new wife, and she got back at him by sleeping with every other pirate in port. The two eventually moved to Nassau, where James faded, and then became an informer for the English Government.

Though Anne lived alone in the wickedest city on earth, no history ever describes her as a victim. She won the respect of the pirates in her own right. When she went to sea with Jack Rackham, she lived and worked like other members of the crew.

Captured with Jack, she disappeared from prison sometime in 1721. Her ultimate fate is unknown.

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Eleanor Guthrie

Not quite a historical figure in her own right, Eleanor and her father represent members of the Guthrie clan, a Scottish merchant family who lived near Nassau and made a fortune dealing with the pirates.

There were no “strong female members” of the clan, like Eleanor, and these merchants made no effort to interfere with pirate politics, but they were a real enough group of people.

Ned Low

Although he had a short career on Black Sails, Ned Low had a long career as a pirate – over 3 years. He was one of the few truly evil pirates, probably a sociopath, who savagely tortured his victims, apparently just for fun.

Low captured over 100 ships, and may or may not have been marooned by his own men for murdering a member of his pirate crew. His actual fate is unknown.

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Benjamin Hornigold

A former privateer, Benjamin Hornigold lost the support of the English government after the end of the War of Spanish Succession (Also called Queen Anne’s War). He began pirating, starting out with a canoe, and building his power until he captained the Benjamin – a warship as large as the Queen Anne’s Revenge.

Hornigold was a pivotal figure in the story of the Caribbean pirates. He literally taught pirating to some of the most famous pirates ever, including Sam Bellamy and Blackbeard, and his influence colored the careers of dozens of pirate ships and over a thousand individual pirates. He might have been a pirate king, but his loyalty to England prevented him from attacking English ships, which reduced his popularity with the pirates.

One of the founders of the Pirate Republic in Nassau, Hornigold was a moderate, who strongly disapproved of harming captives. He took the pardon of 1720 and went back to privateering, dying in a shipwreck several years later.

You can read more about the real Benjamin Hornigold right here.

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The most famous pirate ever is not what you’d expect. Though his early life remains obscure, there are hints that, unlike most pirates, Blackbeard came from a well-to-do family. He may or may not have also had African ancestry.

Wherever he came from, the pirate known as Blackbeard knew how to create terror. But it was terror with a purpose. Paralyzed by fear at his approach, victims gave their utmost cooperation, allowing Blackbeard to take what he wanted without ever harming any of his captives. But, also unlike most pirates, he had a taste for treachery, marooning his own men to increase his share of plunder, then turning on the men who had pardoned him to take up a life of crime again.

Blackbeard met his fate at the hands of a navy lieutenant, his severed head carried back to North Carolina for a reward that never materialized. Legend has it that his body still roams the beaches, trying to get back his lost skull. But that’s just a legend, right?  

Blackbeard will join up for Black Sails season 3, and we’ll report on his legendary exploits. And we’ll also be reporting on new additions to the cast as they show up. Den of Geek is pirate central!

TS Rhodes is the author of The Pirate Empire series. She blogs about pirates at