Black Sails, the epic pirate saga of Long John Silver and Captain Flint that serves as a sex-and-blood-filled prequel to the novel Treasure Island,

But unlike univerally celebrated shows like The Wire, Black Sails remains one of the most underrated series of the Peak TV era.

Building Around a Moving Target

One big reason why Black Sails continues to attract new fans years after its conclusion is Captain Flint. I’ve previously explained why Flint is one of the best main characters in television history. But a hero is only ever as interesting as the obstacles in his way.

Fortunately, the Black Sails cast is full of complex characters who oppose Flint at every turn. In fact, their complicated motivations also underline a key aspect of TV writing structure: each of the main characters in Black Sails represents a different aspect of the show’s central theme, honor.

Let’s take a closer look at the character arcs for the competing protagonists in Black Sails, and see why writing characters who boldly act in direct opposition to each other can lead to a tightly-wound and highly compelling story.

WARNING: MILD SPOILERS AHEAD for all four seasons of Black Sails.

John Silver

Luke Arnold stars as the pirate John Silver in Black Sails

In a series that’s filled with antiheroes instead of true heroes, John Silver (Luke Arnold) is the closest thing we have to a point of view character.

Silver’s addition to Flint’s pirate crew in the pilot episode of Black Sails is the inciting incident that launches the entire series on its four-season collision course. (It also conveniently provides other characters with an excuse to explain how piracy works to the newbie Silver, who is learning the rules of this new world right along with us.)

From his very first moments onscreen, we see that Silver is a man who lives entirely without honor. He is only loyal to himself, and his only goal is to survive.

Luke Arnold is "a hard man not to like" as John Silver in Black Sails

But as he gets drawn further into the web of Flint’s grandiose schemes, Silver’s natural talent for staying alive by lying takes a turn. The more time he spends with Flint’s crew, the more he comes to honestly respect them, and vice versa.

Ultimately, Silver’s skills at manipulation come to rival Flint’s, which makes them natural opponents for the hearts and minds of Flint’s crew. And when Silver finally finds something he actually believes in, he learns that it’s never too late to choose honor… but it may be too late to win.

Captain Flint

Toby Stephens stars as the pirate Captain Flint in Black Sails

While Silver may be Black Sails‘ point of view character, Captain Flint (Toby Stephens) is the driving force of the entire series.

Despite being a pirate and an outlaw, he genuinely believes that he is doing the honorable thing by violently opposing the corruption of England and striving to create a new sovereign state in the Bahamas, where men can live freely without being shackled by the laws of the crown.

Toby Stephens as Captain Flint in Black Sails

Flint’s quest to establish Nassau as a legitimate seat of power in the new world justifies every bloody, vile, and duplicitous thing he does — in his own mind, anyway, and most likely to the audience as well. And just like Silver, the more time we spend with Flint, the further we fall under his spell.

Billy Bones

Tom Hopper stars as the pirate Billy Bones in Black Sails

If Silver is Flint’s rival in terms of manipulating others for his own gain, then Billy Bones (Tom Hopper) is Flint’s rival for the moral high ground.

In many ways, Billy is a mirror of Silver. While Silver is scheming and untrustworthy, Billy is noble and honest. The men love Silver for what he claims to be, while they admire Billy for who he undeniably is. And both men are also expert observers, of Flint and of each other.

Tom Hopper as Billy Bones in Black Sails

As Silver’s arc begins to curve toward a higher purpose in the series’s later episodes, Billy’s curves as well, but toward an embrace of the mindgames and mythmaking that Flint and Silver had previously perfected.

By the end of the series, Billy stands to lose the most compared to where he started, while Silver stands to gain just as much. And standing between both of them is Flint, the fox that neither of them can ever seem to outwit for long.

Charles Vane

Zach McGowan stars as pirate captain Charles Vane in Black Sails

Charles Vane (Zach McGowan) would be the villain of Black Sails, if the series followed a typical format. Instead, Vane starts out as Flint’s arch-rival before going on a hero’s journey of his own. His gradual turn toward the light is a variation on the classic redemption arc that mirrors Flint’s descent into darkness.

However, this is less a result of Vane having a clear change of heart than it is a commentary on just how terrible the other villains in the story ultimately act. While they may all exist on the same moral spectrum where Vane is intially the character farthest from the moral center, his claim to that title is quickly surpassed.

Zach McGowan as the pirate Charles Vane in Black Sails

In addition, Vane also comes to embody another theme that directly connects Black Sails to its source material of Treasure Island: the gap between a story and the truth. Everyone who knows Charles Vane knows him differently, and his story ultimately becomes a legend that everyone interprets in their own way.

The fact that Vane is one of the Black Sails characters who are actually based on a real person further underscores this irony: no matter what we choose to do in life — honorable or not — how others tell our story is never something we can directly control.

(BONUS: Fans of Black Sails may enjoy this summary of the real Charles Vane’s exploits, which reads like a blueprint for the series — and may also indicate who Captain Flint was based on.)

Eleanor Guthrie

Hannah New stars as Eleanor Guthrie in Black Sails

As the reigning powers-that-be in Nassau, Richard Guthrie and his daughter Eleanor (Hannah New) provide the pirates with a stable market for their goods and the only shred of legitimacy that the King of England will recognize in Nassau. But Eleanor is caught between her longing for power and her lust for… well, several people, all of whom want very different things.

Given that trust is hard to come by in Nassau, Eleanor is constantly burning bridges as she tries to assert control over her areas of influence, help Flint in his quest against England, and manage the thorny attachments and unresolvable expectations of her ex-lovers.

Hannah New as Eleanor Guthrie in Black Sails

Like most of the characters in Black Sails, Eleanor is perpetually caught between two undesirable choices, and with every small win she earns another dangerous enemy.

In terms of honor, Eleanor wants to obtain it more than anyone else on the show. She craves legitimacy and respect, and if she can’t find it with the pirates, she’s willing to trade her allegiances to the opposition. But can honor be obtained dishonorably? That question ultimately defines Eleanor’s character arc as a race against time and karma.


Jessica Parker Kennedy stars as Max in Black Sails

Like Eleanor, Max (Jessica Parker Kennedy) is a woman trying to earn respect in a man’s world during a time when such respect was rarely granted, so both women must learn how to seize it for themselves.

But while Eleanor attempts to gain power through traditionally respectable means like finance and bureaucracy, Max is a former slave turned street-smart whore who buys and sells information. As Eleanor navigates regulations and diplomacy, Max masters the nuances of the black market, rising through the ranks of Nassau’s underbelly to become untouchable precisely because of what she knows about everyone else.

Jessica Parker Kennedy as Max in Black Sails

As one of the smartest and most conniving characters in the series, Max gives every other character in Black Sails a run for their money — often literally. Her pursuit of financial independence means she can never allow herself to become attached to anyone else for long, because she perpetually risks being sunk by their foibles and mistakes.

But as a self-made woman, Max must also continually redefine her own personal code of honor. Like her mirror, Eleanor, Max spends the conclusion of her arc desperately trying to determine whether she can truly have it all. The difference between them is that Max gets to make her own rules.

Jack Rackham

Toby Schmitz stars as the pirate Jack Rackham in Black Sails

Initially presented as the show’s wry comic relief, Jack Rackham (Toby Schmitz) has perhaps the most rewarding character arc in the entire series. At first, he appears to be a cartoonish mirror of Silver: while everything Silver touches turns to opportunity, everything Rackham does as Vane’s first mate leads to chaos. But over the course of four seasons, Rackham’s questionable choices become the structural lynchpin that holds the show’s many dueling storylines together, all while he himself matures into… a hero?

Like his real-life inspiration, the infamous Calico Jack, the Jack Rackham of Black Sails is an insecure and scheming striver driven almost entirely by ego. It is extremely important to Rackham that he become known, liked, respected, revered, and remembered, and this motivation drives him to take huge risks in search of even bigger rewards.

Toby Schmitz as Captain Jack Rackham in Black Sails

In his upwardly mobile quest, Rackham learns many difficult and dangerous lessons about the nature of power, the burdens of responsibility, and the illusions of loyalty. That last point resonates most profoundly within his arc, as Rackham wrestles with the idea of loyalty in all its forms. What does he owe the men he sails with? What does he owe his friends, and what do they owe him? What does he owe his partner Anne Bonny and the ever-shifting status of their maddeningly codependent relationship?

Most importantly, what does he owe himself?

In a story that revolves around the unknowability of truth, Jack Rackham comes to serve as the caretaker of the myths that Black Sails is founded on. If Silver is our window into this world, then Rackham is our avatar, the one who seems to be perpetually cosplaying his way through matters of life and death, all in pursuit of his own version of immortality.

Anne Bonny

Clara Paget stars as the female pirate Anne Bonny in Black Sails

In reality, legendary female pirate Anne Bonny (Clara Paget) sailed the high seas as Jack Rackham’s partner, but much about her real life is unknown.

In Black Sails, she is depicted as the bloodthirsty muscle who keeps Jack alive between harebrained schemes. Theirs is a love-hate codependency based on mutual appeciation that is frequently counterbalanced by sour frustration.

Clara Paget as Anne Bonny and Toby Schmitz as Jack Rackham in Black Sails

But Rackham isn’t Anne’s only concern. She also finds herself drawn to Max. This creates a complex love triangle that is further complicated by Jack’s unpredictability and Max’s emotional distance.

As the series progresses, Anne, Jack, and Max must find a way to coexist in pursuit of their goals while somehow keeping each other alive long enough to enjoy the fruits of their illicit labor. In a lawless world where being attached to the wrong person can get you killed, earning a happy ending is never easy.


Zethu Dlomo stars as Madi in Black Sails

Unlike most other characters in Black Sails, Madi (Zethu Dlomo) has power right from the moment we meet her. As the daughter of the Maroon Queen, she is the heir to a free island populated by escaped slaves who will fight to the death to defend their hard-won liberty.

Madi and her people represent the same freedom that Flint is seeking for his own men, which in his mind should make them natural allies. But why should free men risk their own death to fight for the freedom of others? It’s an existential question, but its answer has very real implications for the maroons and the pirates alike.

Zethu Dlomo as Madi in Black Sails

Meanwhile, Silver sees something else in Madi: a different kind of future that doesn’t involve allying with Flint.

Can Silver convince Madi that Flint is a monster before Flint convinces her that he’s a god? And whichever man’s argument prevails, what path toward freedom will Madi choose for herself?

Woodes Rogers

Luke Roberts stars as the privateer and governor of Nassau, Woodes Rogers, in Black Sails

While there are many temporary and situational antagonists in Black Sails — and many of the characters listed here frequently serve as antagonists to each other as their alliances shift throughout the course of the series — in the long game that these pirates are playing, Woodes Rogers (Luke Roberts) is the final boss.

Embodying the British Navy’s official military response to acts of piracy, Rogers’s eventual arrival in Nassau is unavoidable, the destruction he wages is unstoppable, and the tragedies he unleashes are inescapable. (Much of this portion of the story is also completely true.)

Luke Roberts as Woodes Rogers in Black Sails

As the story’s dueling visionaries, Rogers and Flint are equally passionate about how they believe the world should work. Their story’s conclusion depends on the answer to one simple question: which of them is prepared to go farther in making their vision a reality?

How to Write Character Arcs the Black Sails Way

Long John Silver, Billy Bones, Captain Flint, and Charles Vane lead the cast of Black Sails

If you want to write compelling character arcs for an ensemble cast, here are five writing techniques you can adapt from Black Sails showrunners Jonathan E. Steinberg and Robert Levine.

Give your main character a clearly-defined goal, which creates opportunities for obstacles in all forms.

Flint wants a free and sovereign Nassau. To do it, he’ll need enough men who believe in his cause, enough weapons to defeat his enemies, enough fortifications to defend his ship and the city from attackers, and enough gold to pay for it all. Each of those micro-needs is a minor goal that he pursues in service of his ultimate need, and they all come with opponents who stand in his way.

Give your main character a rival in all directions.

As a pirate captain, Flint naturally has professional rivalries with Charles Vane and every other pirate ship at sea. As an aspiring revolutionary, he’s automatically in direct opposition to the monarchy of England, which creates an ideological rivalry that manifests in the arrival of Woodes Rogers. And as the leader of his own pirate crew, he must face threats of treason and insubordination from his men, as well as competition from other ships who might steal his men away, all of which creates charismatic rivalries.

To multiply drama, create characters who mirror each other, apart from one major change.

If Billy were less scrupulous, he would be Silver. If Silver were more aspirational, he would be Flint. If Flint had fewer morals, he would be Vane. If Vane were a woman, he would be Eleanor. And if Eleanor was living on the streets instead of in her father’s mansion, she would be Max.

Everyone has a signature trait.

Many characters on Black Sails are liars, but none of them do it as well as Silver. Many hope to achieve greatness, but none of them are as driven by their vision as Flint. And many are ruthless, but none of them are as ruthless as Vane… for awhile, at least.

Meanwhile, Max is the one you can trust to get anything done, while Billy is the only one you’d ever trust with your life. Being the only person with a specific trait among the ensemble makes it easier for those characters to stand out, and positions everyone else around them at varying degrees of opposition to that same trait.

As the stakes keep raising, the conflicts drive the characters further apart.

In the beginning, Flint, Silver, and Billy are all on the same side, more or less. By the end, each of them wants something very different, and they’re each willing to go to great lengths to achieve it. A win for one of them means failure for the others, which makes every decision a matter of life and death — either ideologically, physically, or both.

Final Thoughts

The season one cast of the Starz series Black Sails

In a show that presents murderous pirates as sympathetic “heroes” fighting for their own destiny against a repressive imperial regime, Black Sails asks its audience to reconsider questions of freedom, morality, and honor from multiple conflicting points of view.

None of the Black Sails characters are ever entirely “right” or “wrong,” and each of them are capable of performing acts of noble heroism and despicable villainy, even in the same breath. Identifying with these characters isn’t always easy, but once we do, we often end up in as many no-win situations as they do, torn between two outcomes that will leave us gutted either way.

That’s the power of writing character arcs that are in constant opposition: for this kind of story to be resolved, some of those arcs will need to be destroyed. And when the audience is emotionally invested in the actions of characters they’ve come to love, the consequences of their actions can feel every bit as crushing as they are inevitable.

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