Major Spoiler Warning: I will be spoiling parts of the end of the series, so best to be avoided until you've finished the show.
Black Sails is a fantastic show which acts as a prequel to the popular book Treasure Island by Robert Louis Stevenson. With the finale of the TV show Black Sails aired, people have many opinions on whether or not the last episode was a good one or not, but one thing is sure - everyone who has read the books knows that where the characters end up in the show set up where the begin the book of Treasure Island very well.
With that in mind, I thought I would take the time here to bridge the gap, embellishing some of the story that would lead to the characters being who and where they are by the time Billy Bones first knocks on the Admiral Benbow. Afterwards, keep reading, as I shall explain my take on the ambiguity of Flint's end in the series.
Added, is some of the end of the real pirate's lives, as they happened in history, despite the liberties taken in the series with regard to their stories, I feel it is interesting to fill in the whole narrative. By my account, the story of Black Sails starts 20 years before Treasure Island and I would estimate around six years passes over the course of the show, leaving 14ish years before Treasure Island starts. So without further ado, here are the next steps of the characters in the books.
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Madi finally forgives Silver after a long contemplation and seeing that her people have not returned to slavery or ended up dead. They move together to Bristol and open up a tavern / restaurant which likely houses pirates from time to time.
Captain Jack Rackham has a few successful years of pirating, making his flag known around the world and securing it as one of the most famous pirate flags ever. Anne Bonny becomes good friends with Mary (Mark) Read and they sail together until the pirate ship is caught. Jack Rackham is hung for piracy, leaving a legacy of tales in his wake. Anne Bonny and Mary Read avoid their sentence by both claiming to be pregnant. Mary Read dies in child-birth and Anne Bonny's end is unknown.
Woodes Rogers was finally released from prison after the judge took pity on him. He would later attempt to publish a book that would restore some of the credit of his name. He became reappointed by the British Isles as Governor of Nassau, as he makes a slow and successful isle of commerce by initiating taxes and riding off of the back of Nassau's now pirate-free claim. Max and Mrs Guthrey likely struck a deal with him and are running the place alongside him. Piracy is kept quiet, but still continues.
Billy Bones washes ashore on Skeleton Island and searches for Flint's treasure. It takes a long time and many vessels show up due to the aftermath of what happened there, but then one of two things happen depending on the fate of Flint. By my account, Billy decides he won't leave without the treasure and creates a map of the island, and after going a bit mad and frequently singing to himself, he finds the treasure and then seeks passage upon one of the vessels. He takes only some of the treasure with him and rallies himself a small crew with the promise of prating and knowing where the rest of Flint's treasure is. Thus becoming a captain of his own crew, and turned to drinking to rid his nightmares of Flint. After a long run of not actually returning to the island for the treasure, his crew-mates abandon him with his chest in Bristol Docks.
Or he gives up on finding the treasure, takes passage on one of the vessels, recruits a crew of his own and his chest contains his own treasures of the seafarin' life. Then one day he bumps into a dying Flint in Savannah, drinking himself to death because of Hamilton, who had left him after their reunion once he learned of what Flint had done. Flint had drawn a map of Skeleton Island with the location of his treasure, and Billy sought to find it after his return to England.
Israel Hands, Ben Gunn and the rest of the surviving pirates go their separate ways. Some, still working as pirates and keeping in touch with Silver, such as Israel Hands. Some other important pirates not seen in the show stay loyal to Silver in this time, such as Black Dog and Blind Pew. Three years before the book, Ben Gunn resolves to find a merchant vessel and usher it to Skeleton Island under the claim he knows where Flint's treasure is, perhaps after bumping into his friend, Billy Bones. After he does not find the treasure, the ship that took Gunn to the island decides to leave without him. He goes slowly mad, but, like Billy, also has the time to find the treasure.
Silver and Madi are fairly happy together for many years. That is until Billy Bones walks in one day with a chest in a barrow looking for drink. Silver recognises Billy immediately, and the adventure of the ocean calls to him in the very same way that Flint told him it would. Billy escapes on foot and decides to hide in as remote a location as possible. Silver sends people after him to retrieve the chest. After asking around for the taverns with the least footfall, Billy finally decides to inhabit the Admiral Benbow, under the paranoia that a one legged seafairing man is hunting him.
Treasure Island begins.
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Now for Flint...
The last time we have a proper scene with Flint he delivers an incredibly powerful speech (kudos to Toby Stevens for his wonderful acting) before Silver offers him an ultimatum and we don't really see what happens next. I believe Silver shot Flint at that moment and had been planning the story he could spin after such an occurrence for some time. The reason I believe this is that more things appear to fit into place.
Firstly, the story told to Madi by Silver is shown in a dreamlike way, and is also resembling a story of Flint going to heaven to be with the one he loves most.
Secondly, the scene after Silver's talk shows birds flying away and the other characters starting towards them, as if an alarming noise happened, like a gunshot.
Thirdly, the episode before, Flint states that if Silver kills flint, even he couldn't spin a story to Madi that would make her forgive him (which is exactly what he does).
Fourthly, him lying, even to those he loves, in the most realistic and manipulative way is exactly representative of who Silver finally becomes to become the nasty character he appears as in the books.
Fifthly, and most the compelling reason, is that the treasure remains in the ground on Skeleton island. Silver still wanted that money before he stopped the war, so it seems more likely that Silver shot him for failing to reveal the location and getting him out of the way for good rather than delivering him to Thomas Hamilton as a very different man and risking him still causing problems. Also risking Flint leaving with Hamilton and going to collect the money anyway.
For me, that is way more compelling and accurate to who Silver's character has become and who he is in the books.
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