Eleanor: When Mrs. Scott — when your father told me that you and your mother had died...[it] affected me a great deal. Must’ve been hard...to live hidden away for so long.
Madi: It was hard to be away from him. The rest of it...a mama that did the best she could with the rest of it.
Eleanor: She must’ve done well. I found myself thinking about it. Of walking away from Nassau, from England, from civilization...one can be happy that way, can’t they? A life of isolation, uncertainty, as long as it is lived with someone you love...and who loves you back? It is possible isn’t it?
Madi: It is.

Max: I came to find Eleanor.
Capt. Jack Rackham: I betrayed you Jack...tried to trade your life for my own personal gain, lied to Ann to her face about it...please, Jack...I beg of you, is there any way you can forgive me? That’s was the general sense of what I thought I might hear, coming from your mouth, were I ever this close to you again.

Long John Silver: I did not want this. Flint is my friend. But I’m not what he is. I have no illusions about it. But for all the dangers he presents...for all his offenses, the one thing he’s never done is force me to choose between him and you. That...you did. But it isn’t too late to find a way to remedy it...You made a terrible mistake...and you paid a terrible price. But we’re at war...and you’re an asset. In spite what’s goin’ on, you are my friend...and the men out there have had their pound of flesh and our men...Billy I could walk out there and tell them the sky is red and they’d believe me. That’s the power you’ve given me. But I have to know this is over... your vendetta against Flint...your need to see him dead or departed from our story. I have to know you’ll never put me to a choice between you again. Swear it and this all ends.
Billy Bones: You chose. Live with it.

Eleanor: ...I am leaving. And as my collateral to ensure that this deal is consummated, he’ll be coming with me to the fort.
Capt. Jack Rackham: This deal? As in the one in which you walk away with all my money? It seems the only means I have in registering any meaningful disapproval of this deal at this point is to kill one or the both of you.

Eleanor: You trust him? Flint? Cast your lot with him?
Madi: What does it matter to you?
Eleanor: Before this war began, before everyone’s roles changed, your father mistrusted Flint as much as anyone in Nassau did. I assume you were in some contact with him all that time...and I’m surprised his feelings didn’t influence you.
Madi: You were my sister. There is very little I remember from when I was young, but I remember this — you were older, you were beautiful. I revered you. When you were told that my mother and I were dead, I have to believe that it affected you. You had just lost your mother. But if things were as I remember, my mother and I were your family, too. And yet, through all the years thereafter that my father cared for you, counseled you, labored for you, he never told you that we were alive. It would have been so easy to lessen your suffering by divulging the secret...and yet he never did. Have you yet asked yourself why that is? My father didn’t mistrust Flint. My father mistrusted all of you.

Madi: The damage done to this alliance was caused by Billy. It may be that the only way to repair this damage is to remove that which caused it.
Silver: Remove him?
Madi: It will be the only way to regain the trust of those slave communities uncertain about what this alliance stands for. And you know as well as I, Billy cannot exist alongside Capt. Flint for long. Sooner or later one or the other must go.

I know she has no love for Flint, nor any sympathy for his cause. I fear the instincts that have awoken in her are more insidious than that. She has begun to believe again that disorder in Nasaau is inevitable...that civilization is powerless either through lack of will or capacity to do anything about it. Civilization has a number of faces. To think them all powerless to alter Nassau’s future is a terrible mistake.

Gov. Rogers

Eleanor: ...I thought I knew who I was...a daughter who usurped her father...a woman who had taken control of a wild place...but always with a man behind me, doing his damnedest to bend it all to his benefit. My father, Scott, Charles, you...so many goddamned men here...too many goddamned men here...
Flint: Woodes Rogers. He’s really so different from the rest of us?

Worry ain’t a good look for a king. Not in a kingdom like this...where loyalty is in short supply.

Israel Hand

Garrett: Long John Silver... all he had to do was open his mouth...say your name...and everyone listened.
Billy: What was it that he said about me?
Garrett: He said the reason Flint’s fleet never got warning about the barricade in the harbor wasn’t because Mr. Featherstone didn’t relay it...it wasn’t because Max intercepted it...he said it was because you never sent it in the first place.
Billy: And they all believed him...
Garrett: I don’t think that anyone actually believed it. You weren’t indicted based on the facts, or our suspicions of your motives. He just said it. I think no one had the balls to defy him.

Capt. Jack Rackham: I watched him defeat Edward Teach, in battle...outnumbered and through sheer force of will, saw his bloodlust with my own eyes. That man will never surrender his position here. He will never allow himself to be defeated by you, or I. Not because we bribed him, not because Eleanor Guthrie told him so. He simply will not allow it to happen. I don’t know where that man went or what designs drew him there. But this I know: Woodes Rogers will be returning. And this fight isn’t nearly over.

Silver: The answer is no. Absolutely, no. If she thought you could win this fight, why would she be offering to sell the victory to us, even for a fortune?
Guthrie: I have had enough of this...and I am ready for it to end.

Black Sails Quotes

Silver: Hang on, you're serious about taking the ship?
Flint: What the f**ck did you think?
Silver: I thought this was how you intended to escape.

There's no way of approaching that beach from the land. And even if it weren't for the soldiers, and even if it weren't for the guns; there's a f**king warship watching over every inch of the bay. A f**king warship that's already killed half your number. A f**king warship that will prevent any approach to that beach via the sea. There's simply no way of stealing that gold. But there might be something else you can steal. The f**king warship.