#Black Sails meta

[helena-thessa]

I’m new to Black Sails so I’m sure this has been said, but it’s wrecking me. S4 spoilers.

I feel like the moment toward the end when Flint straight up panics about Silver possibly getting shot and then kills his own man and sabotages his own plan to save Silver was a full-stop, hold up, pause it right there, what the fuck moment that Silver would have absolutely been stunned by it if he weren’t too far gone in his own fucked up mental headspace and scheming plans.

One of the most insidious things Flint does is kill his closest friend and confidant (as close as he’ll allow someone to be to him as his Flint persona, anyway) because Gates was going to interfere with his plans. The plans came first. The plans always come first. Flint repeatedly has a one-track mind and the will of the Gods to see his plans through (ie creating the storm). Something like friendship can’t stand in the way. Nothing can.

Except—

In this moment near the finale, Flint makes the complete opposite decision. He chooses his friend over his plans. He chooses Silver over what he thinks is the way to succeed, over what’s necessary for the war. He chooses Silver over his plans. In a split second, entirely instinctual and emotional reaction, he chooses Silver.

And Silver was there when Flint killed Gates. He knows what Flint is capable of in moments like this one. He should’ve stopped everything right then and there and realized and been forced to accept how much Flint cared about him, but he didn’t. He couldn’t.

Flint could tell Silver his story and about Thomas, but Silver didn’t tell his own story. He couldn’t.

That is so fucking heartbreaking. This is the real reason he inevitably becomes the villain, not because of Billy’s propaganda or all of the posturing. It’s his mind, his outlook: Survival only. Survival first.

Silver has already shut Flint out when he first realized Flint might choose the war over Madi, even though so many times afterward and so sincerely does Flint promise that she’s a priority and that they’ll save her. Flint has pulled off the impossible before. Silver has believed him and only him capable of pulling off impossible things before. But Silver has already made up his mind and refuses to see or accept a reality where Flint actually cares for him, and by extension, Madi.

Silver is completely lost to his own insecurity? inability to connect and trust and love? once there are actually people in his life who love him that he has forced a story onto those around him that leaves himself out of an actual life with them.

It’s awful. agh it’s so good

[cashmere-caveman]

flint voice all i ever wanted was to walk away from the sea silver voice i never wanted to be a pirate flint voice i feared the man i was about to create. i feared that someone born of such dark things would consume me were i not careful. and i was determined only to wear him for a while and then dispose of him when his purpose was complete. and i thought of that story. billy voice i've watched her follow mad men. i've watched her follow rich men. i've watched her bow before tyrants. but now it's time she had a king. when we're ready, when he's ready, he'll step into the role we've created for him. flint voice when i say there's a war coming, i don't mean with the scarborough. i don't mean with king george or england. civilization is coming and it means to exterminate us. if we are to survive, we must unite behind our own king. billy voice we have no kings here. flint voice i am your king. billy voice but now it's time she had a king. when we're ready, when he's ready, he'll step into the role we've created for him. max voice until then, i remain long john silver. madi voice who is long john silver? silver voice well, that's a very good question. i assume he saw value in the tall tales told about me after that night in the tavern. saw mystery in it, perhaps. use my name upon which to build his story. flint voice one night he was alone on the late watch at anchor in the boston harbour when he sees this man climbing out of the water and onto his ship. a stranger. now, my grandfather thought about ringing the bell, but curiosity got the better of him. the stranger approaches my grandfather and asks him for a little rum. man said that he'd fled his fishing trawler. accused of killing another man. and when asked his name, the man simply replied mr. flint. billy voice when we're ready, when he's ready, he'll step into the role we've created for him. silver voice look, this deal, it's really a terrible idea. there are so many ways it could go wrong. me, i can't help myself. i see an opportunity, i take it. it's a sickness. truly. but you, you can still walk away.

[jaynovz]

Listen. A lot of John Silver meta posts are like 75% there. And the part that gets on my nerves is the *intent*

Assertations that this character is constantly purely calculating and self-aware and consciously scheming and in control are the things that really rub me the wrong way. It discards the strength of the performance and editing and script and the things that that performance indicates as far as expressing vulnerability or lowering the mask.

Does he still keep like five different layers up even while trying to lower two of them? Yeah, of course, we see that on screen.

But for me where a lot of these Silver takes fall short is failing to acknowledge that the character himself doesn't even realize that he's lying half the time because he's the best at lying to himself. And that it's self-defense mechanism and survival instinct and that it's just like breathing. It's a default state.

For many of these interactions, especially with Madi and Flint in s3 and s4, he often thinks he's being truthful.

Anyway, it would be good for people to keep in mind that John Silver is not actually a malicious super villain and is in fact a deeply traumatized and tragic figure.

[mega-ringsandthings-world]

The thing is. The thing is about black sails is. What did they get in the end for all their pain and suffering and blood? Well, nothing. Absolutely nothing. In the end it all came down to nothing and it meant nothing and they were remembered in history as monsters and died as monsters. But yet it meant everything. They failed, every single one of them, but the fact that they failed meant they tried and that meant everything. They failed in the end, so what was the point of it all? Wouldn't it be better off if none of them had tried, if none of them had bled and struggled and fought or even met? But THAT is the point! The point was in the living, not in the dying, not in the failing! It was in the trying! The way they tried because of each other and for each other! The way they tried to beat against something that could not and would not ever move in their lifetimes! Flint tried for Thomas and Miranda tried for Flint and Miranda tried for Thomas and Silver tried for Flint and Mr. Gates tried for Flint and Max tried for Eleanor and Eleanor tried for Max and Charles Vane tried for Elaenor and Mr. Scott tried for Eleanor and Mr. Scott tried for Madi and Silver tried for his men and Billy tried tried tried and the Maroon Queen tried and Madi tried for freedom and Jack tried and Anne tried And Jack tried for Anne and Anne tried for Jack and Anne tried for Max and Max tried for Anne, and Eleanor's grandmother tried for her and Eleanor tried for Woodes Rogers and Woodes Rogers tried for her, and Woodes Rogers tried and Edward Teach tried for Charles Vane and Jack tried for Charles Vane and on Skull island, Silver may or may not have tried one last time and they all tried and it meant nothing and yet everything. Everything. Because the point was not the losing, but that they fought at all to win.

[ravelqueen]

The reason i love the ending of Black Sails (and why i hate like 80% of the discourse around it incidentally) is that no one is right! No one is wrong! They all make the most logical decisions based on who they are and John most of all.

The way I saw John apologists bending over backwards trying to frame it as an OOC decision because John wouldn't do that he loves Flint! at the same time John haters where feeling vindicated bc see he was a dick who only cares about himself and both sides making me claw at my face because the love was the point.

John would have not betrayed Flint if he didn't love him (and Madi)! Because then he wouldn't have cared if they died. But he does! He does so much in a way that is probably fully new to him and scary and it makes him act impulsively in a way he never did before (because as much as his actions often seem lackadaisical, he's a calculating mofo).

So he loves them.

He also, from the very first moments we meet him, has the biggest survival instinct of anyone. He doesn't care about principle or honour or cause he cares about survival.

He's managed to work for this cause and he's applied himself and i think at the moment of the story the Betrayal happens he's even really on board, but a tiger cannot change his stripes and so John Silver cannot change that his fundamental motivator is survival.

And because he loves Flint he wants him to survive more than he wants the cause to win only there he comes into conflict with the fact that Flint's main motivator is the Cause. He and Madi are creatures of principle of "The Cause Is The Cause Because It Is Worth Dying For".

So the confrontation in the forest is exactly this: Flint following his main motivator of the Cause before anything, because that is what he lives for and John just needing him to live, because you can't care about anything when you're dead.

And so it's tragic and heart wrenching because if John hadn't learned to love so well, so deeply, so earnestly throughout the story he would have let Flint go and continue to fight, but he did and he does so and he couldn't.

[erme-aeterna-arts]

no but you see!! eleanor and flint share their backstories with rogers and silver respectively like “this is the worst crime that was done against me, you are the only person on earth i’ve told about it” and then those two just go and do That Crime to them. like with rogers and eleanor it is obviously the raid, and with silverflint it’s the taking of flint’s entire life from him and have it told differently, falsely, the removal of his ability to be the narrator of his own story.

[corvuserpens]

It just occurred to me that all the main characters in Black Sails have some aspects of their outfit/grooming that persist from the first season to the last:

Flint - his beard and the ball earring

Max - little braids that go around the crown of her head and the thick eyeliner

Jack - the scarf around his neck and stylized facial hair

Anne - her hat and masculine outfit

Billy - strings of necklaces and one metal pendant in particular

Vane - half-ponytail with braids plus ear ring

and then there's Silver and Eleanor, the only two mains who change completely throughout the show. Silver because he's an adaptable little shit who accepts influence from the people around him in order to survive, arguable changes the most out of all of them; and Eleanor who does a complete 360º to conform with society's expectations of women to elevate fucking Woodes Rogers and get to be secretly in charge of Nassau.

Given the genius of the writing and consistency in the show's themes, I'm inclined to believe this wasn't an accident.

[agape-emo-eros]

In regards to Black Sails finale I prefer to think that Flint is still alive

Besides it being a good springboard for more stories exploring Flint (did he go willingly rather than kill Silver? Despite of what the war means to him? Who is he without it? Can he and Thomas actually make it work?) I think it's more fun (painful, complicated) ending for Silver in many ways

- it plays into the theme of "civilization can do Horrible Violence without doing ~violence~ in the most recognisable form"

- Silver didn't do ~violence~ so he doesn't see how Madi could blame him for doing Horrible Violence

- he thinks this is a case of "the boy who cried wolf"

- but actually he is being completely sincere. For the first time. For Madi. (Which is unimaginably huge for him) And it Doesn't Matter. He revealed something real about himself and it is rejected as fake

- actually it's even worse: he is understood and he is rejected and it will not change (like he hopes it will)

- part of Silver must know that while he didn't physically kill Flint he did kill a big part of him (and of Madi) and he will forever stew in the wonderful combo of guilt and denial

(And I think it must make the resentment Madi feels for him and whatever kindness she can maybe eventually offer him far more interesting. Because Silver can't even understand what he is being blamed/potential partially forgiven for)

[heycarrots]

There’s been a lot of discourse about the nature of James and Miranda’s relationship. There’s even been a lot of discussion on my podcast about it. One thing I want to make clear is that my podcast is a platform for discussion on all points of view. I’m not going to agree, 100%, with everything that’s said, but it makes the views of my guests no less valid. There’s no right or wrong, here, because this is art and therefore, it is subject to interpretation.

My intent, however, is to attempt to get as close to the original intent of the actors as possible because we look at a show or a film or a play as going through several layers of distillation. Each level purifies the intended narrative leaving its truest essence.

When we make a reduction sauce using an alcohol of some kind, let’s say a red wine, the heat applied to it burns off things we don’t need for flavor. You’re never going to get drunk off of red wine reduction because there’s almost no alcohol left in it. That all gets burned off, leaving only the flavor components, which is what we wanted all along, anyway. We want that extra element that enriches the flavor of the steak, by adding nuance.

So let’s take apart that meal.

We start with the birth of the idea. The story kicks around in an author’s head, trying to get out, growing bigger and more persistent until it outgrows the confines of the mental box inspiration is stored in and has to be let out. That idea, that’s the cow.

The author raises that idea, feeds it, watches it grow, and then, ultimately slaughters it. That sounds awful, but once you have that idea pulsing, growing, evolving and then finally commit the final draft on paper, it is a kind of death. The life of the story comes to an end and it becomes memorialized in a mausoleum. Readers will come to visit, spend time with it, lay down flowers, cherish it, and mourn its passing.

The next level is adaptation. That’s the steak. There are many ways you can slice the story, large roasts encompassing the whole story or a smaller, hyper-focused character study fillet mignon.

A writers room gets hold of the cow and carves it up. They choose what gets cooked and what gets tossed. A GREAT group of writers saves the bones. They take in the entire supporting structure of the piece and while the whole story may not make it onto the screen, they will have slow roasted the bones for a stock. When you watch a show like Black Sails, where themes are introduced that won’t fully be explained or explored until several seasons later, that’s what that is. It is the stock being used to flavor the whole dish. You’ve distilled the entire cow to its purest essence and so every scene, every line of dialogue, every acting choice, encompasses the entirety of the story. A line from episode one is defined by knowledge of the finale and in regard to dialogue, defined by an actors’ knowledge of a character’s backstory. There are many writers rooms who are creating the bones of the story as they go, which means they aren’t starting with a rich stock. You can’t trace back character motivations or choices to begin with because those motivations changed throughout production.

Black Sails, again, isn’t one of those shows. Steinberg and Levine came into the writers room with their stock pot full and sloshing, spilling story everywhere. The richness of the details they were laying can make season one a bit hard to consume unless you are ready for a story on that level. Viewers need to come to the table with some bread to sop up all those character details because we WILL need them later.

Over the course of finalizing scripts and blocking out episodes, the steak is cooked. Like any great steak, this story is medium rare. More juice comes out with every bite. It’s what makes the show infinitely rewatchable. It continues to cook on the plate, but because it wasn’t overdone, it never dries out.

When the actors get ahold of it, that’s the reduction sauce we were talking about. That sauce provides nuance and flavor. That’s the emotion. A line of dialogue on a page is just ink. It’s nothing until it’s spoken aloud. And like any bit of language in this world, it’s subject to interpretation. In this case, it’s the actor who does the interpreting.

I spoke on the podcast about the art of subtext and how huge a role it plays in Black Sails. One example we used is Jane Eyre. It’s one of the most frequently adapted novels in the English language and with each adaptation, we get a new version of our characters. The most volatile and subject to change is Rochester. There are MANY versions of Rochester that I find appalling (including the original beast in the book), but each actor has formed him into something else, based on their performance. Toby Stephens takes Rochester and turns him into a silly tragic romantic, broken many times over by a society he never really fits into, despite the status of his birth. He connects with Ruth Wilson’s Jane because she fully and happily inhabits that space on the fringes that Rochester thinks he needs to climb out of. Jane takes his hand on the outside of the wall, turns him away from the guarded palace and shows him the wild world that was at his back this whole time.

This is what Toby Stephens, Luke Arnold, Louise Barnes, Zethu Dlomo, and really all the actors for whom their subtextual choices make them reflect like prisms, have done with their performances.

In the final distillation, character motivations and emotions are finalized by the actor. Writers can pontificate, the source material lies dead in its lovely tomb, but stories live and breathe by their storytellers.

What we’re left with is Toby’s face telling the world how deeply Flint loves Silver. Every single choice tells this story.

We’re left with Luke showing us how much Silver is repressing in his feelings for Flint. Luke’s face shows us an incredible depth of feeling and a door slamming shut.

We’re left with the incredible intimacy between James and Miranda, which speaks of a decade of shared physical intimacy. There’s an openness, a freeness to it until the moment in episode 3 when Miranda learns that James has found the Urca and is leaving soon to pursue it. She gives some of it away when she says “I thought I’d have you all to myself”. She is mourning the loss of intimacy that she only gets in short windows of time. They aren’t strained because James isn’t attracted to her, but because he’s rarely there. She has him for a few days at a time before he’s off on another hunt. The coldness starts from the moment he tells her he’s leaving in a few days because I believe she thinks he won’t be coming back, that this is the hunt he won’t survive and she’ll finally have lost both James and Thomas. From the moment Richard Guthrie darkens her door, she’s looking for a way to weaponize him and get them out. For her, it’s a race against the clock and she’s willing to sacrifice a bit of her relationship with James in the present to secure happiness for them in the future.

This is also why James still has sex with her before leaving, even though he’s furious for her reading Meditations to Richard. This is how they connect. They connected through physical intimacy in the flashbacks, as well. Him stroking her thumb in the carriage before the kiss. Tactile contact to seal their understanding of each other. Miranda bracing her hands on his chest during important moments in the Hamilton’s home, something she also does to Thomas, to show physical connection, physical intimacy. Miranda thrives on physical touch.

To think that, for 10 years, James is lying there like an object for Miranda to use, is, to me, short sighted. To think that James doesn’t love Miranda outside of a group, is also ignoring the fact that, 10 years on, James will not leave on a hunt (angry as they both are) without physically connecting with her, trying so hard to reach beyond his anger and the wound freshly opened from sight of that book he’s chosen not to look at for probably the better part of those 10 years. The way his hands hover over her back after she comes and he desperately wants to be with her in that moment, like the best of their moments, but he just can’t, speaks to the depth of his love for her.

So many fans of the show point to this sad sex scene as one of the most important character moments for James and Miranda, but I consistently come to the opposite conclusions about WHY it’s important and what we learn from it, because I’m taking my cues from the actor’s choices, not the director or the writers. On the page, in plain ink, he hates having sex with her. Toby and Louise show us, however, that they are trying to recapture a thing that is fleeting, reaching out to each other to patch up an old wound from which the scab has been picked off, leaving it seeping and raw.

From Toby’s performance, regardless of the words he uses years later to describe it, we see not a character who “loves men” or a character who “loves women”, but a character who LOVES. I don’t see Flint defining that love in terms of boxes and parameters. He’s a character who must be coaxed out, but then loves without reason, without a safety net, as he proves with his love of Silver. As was also referenced by a guest on the podcast, he places a sword in Silver’s hand and says “do it”.

Anyway, this post got away from me and took several turns, but the love between James and Miranda being dismissed by so many in the fandom has been bugging me for a while and I just needed to emotionally vomit on tumblr.

[lumisails]

Thinking of how every single found parent/child relationship (or relationships that get the closest to it) is doomed in Black Sails. Flint and Eleanor. Teach and Vane. Miranda and Abigail. Gates and Billy.

Not a single one of these has both characters survive. Abigail loses her innocence by watching someone who could be a mother figure to her die. Billy would never got as far as he did in season 4 if Gates was alive. Eleanor wouldn't have died if she had stayed on Flint's side. Teach and Vane never had a chance.

[helena-thessa]

In the shark hunting scene, it's beautifully subtle yet so starkly on display for us that Flint is the only one capable of committing real violence. It's Silver's idea, Silver hands him the harpoon, and certainly Silver is the one who holds onto the rope like his life depends on it. But Flint is the one who throws and spears the shark. Flint is the one who then knifes it dead.

Lest we forget that Flint's violence and Silver's scheming are the driving force of the narrative.

In case we didn't get the point made right beforehand when Silver failed as quartermaster to administer discipline over the stolen rations and Flint had to step in and do it for him, further straining his always tenuous captain-to-crew relations.

Before we delude ourselves into forgetting that Silver's aversion to real violence will inevitably put Flint directly into harm's way.

sfklsdflsjdflksdkf

[jaynovz]

I'm watching 1.7 and the break in Flint's voice when Gates is questioning him in the stable and he's like "I'm trying to answer the question" is devastating. The facial acting that Toby is doing here is like, he does great body language here and the trembling voice and nervous swallowing and darting eyes, you can see him trying to stave off some kind of extreme anxiety attack. Because. Like. God the flashbacks he must be having to London and Hennessey and Alfred Hamilton. Anyway, what he is saying just gets more and more desperate throughout the exchange, but legit he is trying to level with Gates the only way that he can in this moment. There is no version of Flint right now who could tell the whole truth, bc of his background, bc of the trauma, bc of what happened last time he trusted someone like that. So when we see what appears to be a mental BREAK, and he tells Gates his vision of sequestering a portion of the Urca gold for the future of Nassau and their men, that's him trying to explain his motivation the best way he can.

And the worst part is, he just sounds crazy and meglomaniacal and Machiavellian and DERANGED. It's exactly the wrong thing to say to Gates at that moment, they have already broken apart, it's too little too late, it's ten years too late!! Gates is hearing a lying maniac being conniving and cold and awful about Billy. But tbh, when I hear Flint say "He fell. Why? What do you think happened?" I just hear someone that WE KNOW doesn't know in his heart of hearts WHAT HE DID, WHAT HAPPENED, and he just... it would be easier if someone just told him.

I know we joke about Flint being full of SHIT, and he is in MUCH of the show, he does SO MUCH LYING. But this entire exchange doesn't feel like that. It feels like he's cracking and reaching and grasping and trying. And he has no earthly idea what path he would even take to get Gates back on side.

Gates says, "This is what we do. You orate and you dissemble and I look the other way..."

And the saddest fucking part, the most tragic of the tragedy is that HE'S NOT WRONG. That is what they do!! and it's. It's over! It's too much!

But poor fucking Captain, he just... He doesn't know how else to be.

And with regard to SilverFlint, and their arc... I've been thinking this go round about why it's different from Flint's relationship with Miranda or with Gates or with anyone...

And, well... It really is just a case of finding deep understanding from a person you never expected, isn't it?

At first it is extremely begrudging, because he doesn't have another choice, unwilling allies due to strife. But eventually it does becomes voluntary.

At its core, I think the reason that relationship is different, is because that becomes clear to Flint over time, and then he is able to offer up all the sides of himself to be further collated and understood.

And then faster than the speed of fucking light we get to 3.10 and 4.9: "You asked me where I began, and I felt that you were entitled to an answer. To the truth." and "I cannot do it without you." Silver says, "We might be friends by then" and by fuckin god they ARE. "As my partner as my friend" and "You know of me all I can bear to be known. All that is relevant to be known. That is to say, you know my genuine friendship and loyalty." So, what I've been circling is... sitting down in the woods and just telling Silver everything that happened in London is exactly what he can't do with Gates in 1.7 :////

[livila]

For anyone with Nebula, Ladyknightthebrave has just released a 2 and a half hour video essay on Black Sails! I’m guessing she’ll release it on YouTube too.

[max-nolastname]

types of story that different black sails characters think they're in:

jack: typical underdog overcoming unbeatable odds story; he is the main character and the show is 100% about him and his joseph campbell hero's journey. he is like achilles seeking eternal glory. he is also like gilgamesh, seeking immortality because he's afraid of death

flint: one of those fairytale retelling stories from the villain's pov; he is the fire-breathing dragon/big bad wolf/wicked witch that his village has ostracized, chased out of his home with pitchforks and torches because they feared him and what he is and what he stands for. he knows that in another show, a more popular show, the story would be told from the pov of the villagers about the dangers that lie beyond the village walls and into the forest...but this is HIS show and in HIS show HE is the one that survived the villagers not the other way around and HE is the one that has been wronged and he WILL see them pay for it

miranda: at first she thinks she is the witty and cunning heroine of a regency period romance novel. she is critical of high society and it's archaic and sexist traditions, turns her nose up at the institution of marriage and yet against all odds finds a true partner in thomas. she thinks herself happier and smarter than her peers, for finding a way to explore her sexuality freely and still keep her high status. she is caught in a whirlwind romance with a handsome naval officer and well....then her story turns into a tragedy and a decade caught in lifeless loveless joyless limbo where she is sidelined into the background of someone else's story

max: overly aware that she is in A Story and that she is Not The Main Character; the spotlight is never on her, she will never take centre stage. in fact, she is in the wings, or perhaps watching the show from the back of the theatre as the stage manager, setting the scene and directing others to pull ropes, shine lights, open and close the curtains so that other actors can strut and fret their way around the stage

billy: revenge quest story! thinks he is the good guy, there to protect his friends and get revenge on the tyrant who killed his father. gains some genre awareness and realizes that he is not, in fact, the main character, but rather a side character caught in a romance between his captain and quartermaster and if he really wants to survive he's really gotta break them up

madi: a story of hope told around a campfire, passed on from generation to generation so people don't forget about the time that an island of maroons stood up to a seemingly eternal and unbeatable empire. some days, it's a cautionary tale, on how volatile solidarity can be with divisions like class, race and gender .... or how revolution necessitates violence that people who are comfortable in their oppression rather not pay... but no empire lasts forever and nothing is inevitable. the story sticks in the hearts and minds of future revolutionaries and someday someone somewhere will pick up the torch and continue the fight

season 1 walrus crew: workplace comedy

silver: [redacted]

[rapselsstuff]

There could never have been a happy ending to black sails. If the writers had said “and so they won the war and freed all the slaves and defeated all the English and lived happily ever after“, we would not have believed it, because we know, historically, that it isn’t true. And even a smaller, less complete victory would have been unbelievable. “They lost the war but found happiness regardless” - would they though?? “Silver made them give up the war and Madi and Flint forgave him” - are you sure?? Madi and Flint both made their entire purpose a war they were destined not to win. Both of them would have sacrificed Silver, and anyone else, to win it, and it would have been in vain. There was no way for them to be happy, not ever.

So what the writers gave us in the end was a soothing story. There are days when I believe that Flint is happy in Savannah with Thomas. There are days when I believe that Silver and Madi found a way to move forward together, and there are days when I don’t. In the end, a story is true or untrue depending on people’s belief. If you want to believe that black sails has a happy ending, then you can, and it does. And if you want to believe that the ending is horrifying, then you can, and it is. I think one of the most brilliant things the black sails writers ever did is giving us an ending that is never just one thing, just like Silver, just like Flint, just like the entire show.

[corvuserpens]

Y'know, something that's very elucidative to me regarding John Silver's character, and in a way Flint's character, is that despite him not being the one in a romantic relationship with Madi (in fact I believe his dynamic with her is more of a brothers-in-arms, united for the same cause, that later transforms into something bordering on a mentor/pupil dynamic or even almost a father/daughter dynamic but not quite), Flint ended up understanding Madi as person FAR better than Silver ever did, or could.

So much so that Flint knows Madi would never allow anything to jeopardize the start of the war or its success: not her own life, not Silver's life, nor any promises of safety for her people and her people alone in her maroon encampment - nothing. And he's right! Madi herself confirms it to Woodes Rogers toward the end of S04. Silver might have fallen in love with Madi, but he never actually saw her. And if there ever was an instance when he did, I don't think it was voluntary and it only fed into his own selfish desire to protect her at all costs, not just to himself but to her, too.

Silver also knew she would stop at nothing for the revolution, he knew that even if she were to die, they would make a martyr of her and she would have been fine with that because even dead, she would have accomplished what was necessary, which was to make the war explode and the revolution set in motion. Where Silver failed but Flint did not, was that he was more scared of losing her than he was of losing the war. Which is very human for someone who is definitely not as idealistic as either Flint or Madi, but still selfish and in a way, cruel.

Flint and Madi understood each other completely and made this silent pact to do anything to make their plans go forward, always with the intent to keep each other safe whenever possible, but willing to let the other die if all other options had run out, and they would hold no grudges toward each other should it come to that and they happened to survive. And Silver... Silver didn't. He loved Madi with all his heart, but he never understood her. Not enough to respect her wishes, anyway.