Captain James Flint’s crew in Black Sails is not exactly a workplace where you expect a quiet Monday morning meeting and a nice HR policy. The Walrus is a floating battlefield of ambition, betrayal, loyalty, and extremely dangerous people who somehow manage to make pirate democracy look both brilliant and completely exhausting.
What makes Flint’s crew fascinating is that the strongest members are not always the best fighters. Survival in Nassau requires intelligence, adaptability, influence, and the ability to read Flint himself, which is arguably more dangerous than facing the Royal Navy.
This ranking considers:
• Importance to Flint’s campaigns
• Leadership ability
• Combat skill
• Intelligence and strategy
• Loyalty and influence
• Overall impact on the story
Some characters technically move between crews and alliances, because in Black Sails loyalty lasts about as long as a calm day in the Caribbean.
12. Morley
Morley is memorable because he represents the old guard of Flint’s crew. He is one of the few men willing to question Flint openly, which takes either courage, wisdom, or a complete lack of self-preservation.
Possibly all three.
Morley understands something many others ignore. Flint’s brilliance comes with a cost. He sees the danger behind Flint’s obsession and recognises that the captain’s plans often leave a trail of bodies behind them.
His problem is influence. He knows something is wrong but lacks the power to change events.
Strengths
• Experienced sailor
• Understands Flint better than most
• Willing to challenge authority
Weaknesses
• Limited leadership ability
• Unable to adapt politically
• Outplayed by Flint
Morley is important, but on a ship full of legends, he never reaches their level.
11. Randall
Randall is not a warrior, strategist, or political mastermind, but judging him only by those standards misses the point.
Among the violence and ambition of Nassau, Randall represents the ordinary people caught inside the pirate world. He survives through loyalty and usefulness rather than intimidation.
He also gives us some of the show’s surprisingly human moments. In a series where everyone is plotting five moves ahead, Randall feels refreshingly honest.
Strengths
• Loyal
• Hard-working
• Trusted by the crew
Weaknesses
• Limited combat ability
• Little strategic influence
Every pirate ship needs people who keep things functioning. Not everyone gets to dramatically stare into the distance planning revenge against civilisation.
10. Joji
Joji is one of Flint’s most reliable fighters. He does not dominate conversations or chase power, but when violence starts, he is exactly the kind of person you want nearby.
Quiet characters are easy to overlook in Black Sails, mostly because everyone else is delivering speeches like they are auditioning to overthrow an empire. Joji simply gets things done.
Strengths
• Skilled fighter
• Loyal crew member
• Dependable under pressure
Weaknesses
• Limited character influence
• Rarely takes command
A valuable pirate, even if he lets his blade do most of the talking.
9. Joshua
Joshua is another example of a solid crewman who helps make the Walrus effective. He lacks the legendary reputation of Flint’s closest allies, but his reliability matters.
Pirate crews survive because of experienced sailors, not just charismatic captains.
Strengths
• Experienced
• Practical
• Reliable
Weaknesses
• Not a major decision maker
• Overshadowed by bigger personalities
A good pirate in a world filled with exceptional ones.
8. Gates
Hal Gates deserves far more credit than he often receives. Flint may be the visionary, but Gates is the person trying to keep the ship from tearing itself apart.
Every ambitious leader needs someone willing to say, “Maybe starting another impossible war is a bad idea.”
Flint rarely listens, obviously.
Gates understands the crew emotionally. He manages personalities, builds trust, and provides stability. Without him, Flint’s early command would have collapsed much sooner.
Strengths
• Excellent quartermaster
• Respected by the crew
• Loyal friend
• Experienced sailor
Weaknesses
• Too trusting of Flint
• Less ruthless than his rivals
Gates is proof that good leadership is not always about being feared.
7. Billy Bones
Billy Bones has one of the most interesting journeys in Black Sails. He begins as the moral centre of Flint’s crew, a man who believes pirates should stand for something more than greed.
Then Nassau happens.
Watching Billy become harder and more ruthless is one of the show’s strongest arcs. He learns politics, propaganda, and manipulation, although he never quite reaches Flint’s level.
Few people do.
Strengths
• Natural leader
• Physically powerful
• Brave fighter
• Inspires loyalty
Weaknesses
• Emotional decisions
• Struggles against better strategists
Billy is dangerous because people believe in him, and in Black Sails, stories can be more powerful than swords.
6. Mr De Groot
De Groot might not have the dramatic reputation of Flint’s other allies, but he is incredibly valuable.
He represents professionalism. He knows ships, understands tactics, and cares about practical survival over impossible dreams.
Basically, he is the person asking sensible questions while Flint prepares to gamble everyone’s lives again.
Strengths
• Excellent sailor
• Tactical knowledge
• Experienced officer
Weaknesses
• Limited political influence
• Not as ambitious as others
The Walrus needed Flint’s imagination, but it also needed people like De Groot keeping it afloat.
5. Ben Gunn
Ben Gunn does not get the same level of attention as some of the bigger characters, but his connection to the wider Treasure Island mythology makes him important.
He embodies the strange, unpredictable future awaiting many pirates after the golden age begins to fade.
Strengths
• Survivor
• Adaptable
• Resourceful
Weaknesses
• Not a major commander
• Less influential during Flint’s peak
Sometimes surviving is the greatest skill of all.
4. John Silver
John Silver’s rise is ridiculous when you think about it.
He begins as a cook with no reputation, no fighting experience, and no real understanding of pirate life. Somehow, he becomes one of the most powerful figures in Nassau.
Silver’s greatest weapon is people. He understands stories, fear, loyalty, and perception. Flint builds power through vision, while Silver builds it through understanding what people need to believe.
Strengths
• Exceptional manipulator
• Charismatic leader
• Highly intelligent
• Adapts quickly
Weaknesses
• Not a traditional warrior
• Often driven by personal attachments
Silver proves that the sharpest weapon on a pirate ship is not always made of steel.
3. Charles Vane
Vane is not permanently part of Flint’s crew, but their alliance becomes one of the defining forces in the series.
At first, Vane seems like pure chaos. Violence first, thinking later. The brilliant part of Black Sails is revealing there is much more beneath that reputation.
Vane genuinely believes in freedom. His methods are brutal, but his philosophy gives him more depth than the typical pirate warlord.
Strengths
• Elite fighter
• Fearless leader
• Strong principles
• Inspires followers
Weaknesses
• Reckless
• Struggles with compromise
Vane is the kind of person you absolutely want on your side and absolutely do not want making the entire plan.
2. Anne Bonny
Anne Bonny is not technically a Flint loyalist, but few fighters in the series deserve a higher ranking.
She is terrifying because she is direct. While others are creating complicated political strategies, Anne usually solves problems with a blade and a terrifying amount of confidence.
Yet reducing her to a fighter ignores her character development. Her journey with identity, loyalty, and independence is one of the strongest personal stories in the series.
Strengths
• Elite combat ability
• Fearless
• Loyal to those she trusts
• Strong survival instincts
Weaknesses
• Can act impulsively
• Avoids leadership roles
Anne proves that quiet intensity can be louder than any captain’s speech.
1. James Flint
Was there really another choice?
Captain Flint is the centre of Black Sails because he is brilliant, inspiring, terrifying, and occasionally the biggest threat to his own crew.
He is a strategist capable of challenging empires. He understands naval warfare, politics, mythology, and the power of reputation. Flint does not simply want treasure. He wants to rewrite the world.
A casual goal. Nothing too ambitious.
His greatest strength is also his greatest flaw. He can convince people to attempt the impossible, but he sometimes forgets they are people rather than pieces on a board.
Strengths
• Genius strategist
• Skilled naval commander
• Powerful fighter
• Charismatic leader
• Relentless determination
Weaknesses
• Obsessive
• Manipulative
• Will sacrifice almost anything for victory
Flint is the best member of his own crew because nobody else combines intelligence, courage, and sheer force of will like him.
Flint’s Crew Was More Than Pirates
The brilliance of Black Sails is that Flint’s crew never feels like a simple collection of criminals hunting treasure. They are sailors, rebels, survivors, dreamers, and deeply flawed people trying to control a world that is changing around them.
Some follow Flint because they trust him. Some fear him. Some eventually realise they need to stop him.
That tension is what makes the Walrus one of television’s greatest pirate crews.
