Black Sails: 10 Hidden Details About The Main Characters Everyone Missed

For centuries, pirates have been a fascinating subject in history and media.  Though they technically have existed since ancient times, the modern image of a pirate comes from the Victorian era which was popularized by works such as Robert Louis Stevenson’s Treasure Island and several movies including the Pirates of the Caribbean franchise.

In this same vein, Black Sails was a pirate-themed television show that ran on STARZ for four seasons with Michael Bay credited as one of its executive producers. 

A prequel to Treasure Island, it featured characters of literary and historical origins with interesting hidden details.

Eleanor Guthrie – Betrayed Her Male & Female Lovers

One of the lead female characters in Black Sails, Eleanor Guthrie is the daughter of a black marketeer and runs a pub in Nassau (the future capital of the Bahamas) to continue her father’s operations in selling smuggled goods from pirates.  However, she gains a lot of influence over the pirates she deals with and makes a habit of betraying those who fall in love with her.

These include male lovers such as Captain Charles Vane, and female ones like the prostitute Max.  The main reason for her betrayals was power, which in Charles’ case was using him for monetary gain. But for Max, Eleanor cast her aside in order to build her own trading empire which fell apart in the end.

Max – Went Through The Same Character-Arc As Eleanor

Another important female character, Max’s story almost parallels Eleanor’s, which is ironic since they are on-and-off-again lovers. Instead of exchanging money for power, Max uses her body as she becomes caught up in a three-way relationship with pirates Anne Bonny and John ‘Jack’ Rackham.

Though in the third season, “Max must choose between betraying Anne’s trust and retaining the power she’s worked so hard to acquire in Nassau” according to VICE.  While she does lose this power, Max ends up out-living Eleanor and thriving successfully.

Madi – Wasn’t Mentioned By Name In Treasure Island

Historically, the Maroon people were a community of ex-slaves who fled to isolated places, mainly islands and mountainous areas.  Despite their isolation, they had various conflicts and rebellions against the British navy and Dutch colonists who threatened to take away the land they claimed. In Black Sails, this community is represented by Maroon Island and its self-proclaimed Queen, whose daughter Madi becomes involved with Captain James Flint’s pirate crew.

RELATED: SHE’S A MAD, MAD QUEEN: 10 SIGNS DAENERYS WAS ALWAYS GOING TO BE GAME OF THRONES’ ULTIMATE EVIL 

In particular, Madi becomes lovers with “Long” John Silver of Treasure Island fame. Now in Stevenson’s book, it is mentioned that Silver married a woman who’s implied to be African, although no name is given. So it’s assumed that Madi is supposed to be this character, or at the very least inspired by them.

Billy Bones – Came Up With The Black Spot Threats

Originally known as William Manderly, Billy Bones is another character who appears in Treasure Island besides John Silver.  With that said, Billy’s role is much larger in Black Sails than in the book; in the latter, he is largely responsible for making Silver into the feared pirate that he becomes.

For instance, prior to Silver adopting the method, Billy sent out papers with black spots on them as threats to those who would die by Silver’s hand. By the time Treasure Island happens, Billy gets targeted by Silver for having a map that belonged to Flint.

John Silver – Got His Leg Amputated Differently Than In The Treasure Island Book

Considered to be the antihero of Treasure Island, John Silver is a well-known figure in literary fiction. While he’s motivated to obtain the treasure that was buried by Flint using the map that Billy stole, he forms a bond with the novel’s young hero Jim Hawkins.

In Black Sails, the character’s complexity is portrayed through Silver’s opportunist acts, despite the sympathy he develops for the crew of the Walrus. There are some notable differences, such as the origin of Silver’s peg-leg.  While his “lower left leg is amputated” in the show, he “lost his leg up to his hip” in the Treasure Island book.

Anne Bonny – Based On A Real Person

While Eleanor may have commanded respect from men through her trading network, she’s got nothing on the fierceness of Anne Bonny. Being Jack Rackham’s partner-in-crime, Anne is the only female pirate in the Black Sails series who plays a large role in the story and happens to be based on a real person.

The real Anne Bonny, whose original name was Anne Cormac, was an Irish immigrant stuck in a loveless marriage before getting involved with Jack. According to Britannica.com, the pirate essentially bought Anne from her husband. In Black Sails, Jack kills Anne’s husband instead of offering a divorce payment.

Jack Rackham – Historically Known As ‘Calico Jack’

During the Golden Age of Piracy, which is when Black Sails takes place, there were several pirates of noteworthy fame that existed during this time. Among these was John ‘Calico Jack’ Rackham, the inspiration for John ‘Jack’ Rackham in Black Sails.

The name ‘Calico Jack’ was because of “his taste for clothes made of brightly colored Indian Calico cloth,” as stated by ThoughtCo. Fittingly, Black Sails highlights Jack’s stylish tastes quite frequently. Compared to the likes of Anne Bonny and Mary Read, another famous female pirate from the same era, Jack was not a very competent pirate, which the show gets right to an extent.

Blackbeard – Had More Wives Than The Show Implies

Apart from having two female pirates on his side, Rackham is also credited with creating the famous Jolly Roger flag with the skull and crossbones that became a staple for pirate ships in fiction. Arguably, the most famous pirate from the Golden Age of Piracy was Edward Teach, better known as Blackbeard.  So naturally, he appears in Black Sails from the third season. 

Now according to an Inverse interview with Blackbeard’s actor, Ray Stevenson, “he’s one of the most historically documented pirates…but history, as we know, is written by victors and sensationalists.”

This, in turn, leads to some questionable elements in Black Sails; for example, Blackbeard’s number of wives. While only nine get mentioned in the show, the real number is presumed to be considerably higher.

Charles Vane – Died Later In Real Life

Captain of the pirate ship known as the Ranger, which really existed, Charles Vane is another famous pirate who had “Calico Jack” Rackham under his wing before Jack left to do his own pirating with Anne and Mary. In Black Sails, Charles, Jack, and Anne are all members of the Ranger’s crew, while Mary only shows up at the very end of the series.

Regarding Charles’ death towards the end of the third season, while the pirate was captured and hanged by the British, these events happened around five years later than in the film. To be exact, Vane died on March 29, 1721.

James Flint – Is Bisexual

Much like Pirates of the Caribbean, Black Sails is mainly known for its action scenes and melodramatic tensions. But what many people seem to overlook is that several of the main characters are of bisexual orientation. Apart from Eleanor and Anne, the other major character considered to be bisexual is Captain James Flint.

Prior to the events in Black Sails, Flint served in the British navy but was forced to become an outlaw because, as stated by VICE, “England took away the one thing he cherished most: his boyfriend.”  

Yet this only gets touched upon in Black Sails’ second season, while the rest of the series concentrates on his affections for his male lover’s wife. Almost like the show’s creators got cold feet about depicting a bisexual man when having bisexual women is apparently fine.