The flashbacks in 4x09 are easily my favorite scenes in any show. I was ruined over them, like got teary while standing in my kitchen making toast one day just thinking about it.
Silver asks: "What are we looking at?" Flint replies: "Nassau, thereabouts. A few days over the horizon, just waiting for us. Can't you see it?"
Flint is really asking Silver: Do we share the same vision of the future? Is there no daylight between us? Can you see the way the world could be, in spite of the way that it is?
And in the end, Silver couldn't. He could only see the horror and the loss.
The sword fighting flashbacks that follow add an additional layer of heartbreak, because it's almost as if we aren't meant to witness them.
The dialogue and the looks between Flint and Silver are so intimate and vulnerable. “You know my story" vs "You know of me all I can bear to be known". The unspoken love between them and this looming insurmountable divide.
I watched Black Sails when it first aired and I am still haunted by these scenes to this day.