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This is set in 1715, soon after King George has taken the throne left vacant after the death of Queen Anne. Captain Flint (Toby Stephens - Die Another Day ) leads his pirate crew to attack merchant ships on the high seas. One of the sailors aboard such a ship, John Silver (Luke Arnold - Half Magic ), tries to escape the carnage by pretending to be the ship's cook. The pirates need a cook, so they let him join the crew. He does not want to escape yet, because he has a plan to get rich first.
Flint is after a page that contains the schedule of a Spanish treasure galleon. However, Silver stole the page from the real ship's cook. When the pirates take him back to their base, New Providence Island, he aims to sell it to a rival pirate captain. A sharp-eyed whore named Max ( Jessica Parker Kennedy ) spots what he is up to, and offers her services as a middle-man.
Captain Flint needs to find the missing page, because without it he has nothing to offer his crew. He also has to cope with a rival in the ranks, an uppity underling who wants to replace Flint as Captain. And since the job is elected by the crew, the missing page is more vital than ever.
Captain Flint is only mentioned in passing in Treasure Island , but he buried the treasure that his former cook, John Silver, wanted so badly to retrieve.
Captain Flint (Toby Stephens - Die Another Day ) explains his plan to Eleanor Guthrie. He wants to use the gold from the Urca De Lima to finance the development of the island as a nation of thieves. The pirates could become farmers and soldiers, a militia strong enough to withstand the Spanish Empire – or the British. Basically he outlines the US rebellion of 1776, sixty years earlier.
The Lady of New Providence has been carrying on a lesbian affair with Max the whore ( Jessica Parker Kennedy ). But now she has a decision to make – the lady or the loot? In all fairness, the whore had the same choice and chose to sell out her lover in exchange for the cut of the sale.
Vane and his sidekicks go to meet Silver (Luke Arnold - Half Magic ) for the exchange. It is at a remote section of beach, where wrecked ships are dumped and the lepers live. However, Vane does not trust Silver to make an honest trade. Rackham is trusted with a massive supply of precious black pearls.
Captain Flint has his clue to the route of the Spanish treasure ship. They need another ship to double their chances of success. The obvious source is the man in charge of the fort - Captain Ben Hornigold, an old man with Jacobite sympathies. However, there is another option. Rackham proposes than Flint makes an alliance with his arch-rival Charles Vane.
Eleanor Guthrie oversees the negotiations, and will oversee the agreement. Vane goes along with this, because he wants to get back together with her. After all, she is single ever since Max ( Jessica Parker Kennedy ) fled. But did Max really make it to safety off the island?
Gates takes command of Vane's old ship, so Billy Bones gets elected Quarter-master of Flint's ship. The first thing they must do is careen the hull. However, the surveyor points out that the beach is not suitable for the task. Silver (Luke Arnold - Half Magic ) is not a good cook, and has never barbecued a pig before. The crew are distracted by the f*ck-tent. All in all, this is a disaster is waiting to happen.
A week has passed since Eleanor double-crossed Vane and took his ship. He has now become an alkie. Rackham sticks with him, because after losing the pearls he has nowhere else to go. A few other crewmen also stay loyal, but only because they get free goes on Max ( Jessica Parker Kennedy ).
A ship arrives from the Guthrie Trading Company in Boston, Massachussets Colony. This is the source of Eleanor's power - she is the pirates' fence, and her grandfather's company sells the stolen cargos on their trading route along the ports of the thirteen colonies. She wants Captain Burgess to hand over his ship's cannons, He replies that he does not want to end up in a shallow grave near Cambridge. This is a reference to the town where Harvard is based - although it was founded a century earlier by the Regicide, Hugh Peters.
Flint's ship closes in on the merchant vessel, which is as well-armed as a warship. It has thirty-two guns to protect against pirates, and sixty men to guard the cargo. Flint's accountant is nervous, because he has never been in battle before. Billy Bones tries to give him a pep-talk.
Silver (Luke Arnold - Half Magic ) has been left with Eleanor for safe-keeping. Without the support of her family's trading company, her position is untenable. She calls a meeting of the remaining captains, and proposes to start her own company.
Captain Flint (Toby Stephens - Die Another Day ) has boarded the merchant ship, but the Captain has secured the lower decks. We discover why Mr Scott is not among the trusted crew.
Anne Bonney has not had much to do so far. Her part in the story was to be muscle for Rackham. Now she gets to be a major character in her own storyline. She is sick of what's left of her crew having sex with Max ( Jessica Parker Kennedy ), so she plots with Eleanor Guthrie to have them all murdered. Silver (Luke Arnold - Half Magic ) gets coerced into the plot.
The crew has elected the accountant as the new quartermaster. Billy was lost overboard in a tragic accident, just as his friend was lost in the careening incident. The Bosun is suspicious of Captain Flint (Toby Stephens - Die Another Day ), who was the last man seen with both of them.
The crew has elected Silver (Luke Arnold - Half Magic ) as the new cook.
Rackham is left in charge of the brothel, and is perplexed by its apparent inability to make a profit. Max ( Jessica Parker Kennedy ) advises him Set your house in order!
Vane has sailed up the river to a logging camp. The man in charge is the one who haunts his nightmares.
Captain Flint (Toby Stephens - Die Another Day ) knows the Spanish treasure ship is nearby. But The crew are mutinous dogs! Only John Silver (Luke Arnold - Half Magic ) is loyal to the Captain. The mutineers are so keen to start trouble that they will sacrifice the other ship to the Spanish rather than try to capture the treasure.
There is a new Captain on the high seas. His name is Lowe, and he is a brutal thug. Eleanor Guthrie ( Hannah New ) has enough on her plate, getting Captain Charles Vane (Zach McGowan - The 100 ) to attend meetings of the town council.
In the flashbacks, we learn that Flint was once a Captain in the Royal Navy. Yes, just like that loveable rogue Jones in Once Upon A Time , he is a gamekeeper turned poacher. He befriended another young gentleman, Thomas Hamilton (Rupert Penry-Jones - The Strain ).
Rackham has a plan to get captaincy of a ship. As leverage, he can offer info supplied by Max ( Jessica Parker Kennedy ). However, Anne is regarded as toxic by the pirates.
Captain Flint (Toby Stephens - Die Another Day ) and his arch-rival Captain Charles Vane (Zach McGowan - The 100 ) have to come to an agreement. Vane has a hostage who can bring about Flint's end goal, the liberation of the Nassau colony, faster than the gold from the Urca treasure ship. In fact, if the pirates rob the Spanish treasure this would cause a diplomatic incident and undermine the the plan. Unfortunately, the promise of the treasure is the only thing keeping the crew loyal to Flint.
Rackham sets sail on his first voyage as Captain. Unfortunately the prize that Max ( Jessica Parker Kennedy ) told him about is being hunted by a rival pirate with a bigger ship and crew.
Anne is unhappy at being left behind. She decides to cause trouble at the brothel, despite her former relationship with Max.
Max ( Jessica Parker Kennedy ) has to clean up the mess after the previous episode. She lets Anne stay at the brothel while she sorts her life out.
Eleanor tries to save the hostage, which puts her at odds with Charles Vane. The two women have a conversation which mirrors one between Anne and Max, insofar as they both believe that a person's suffering makes them stronger as a person.
Flint (Toby Stephens - Die Another Day ) stands for re-election as Captain, with his plan to offer pardons to the crew in exchange for the hostage. Billy has another way to get pardons, courtesy of a bounty from the Royal Navy.
Silver (Luke Arnold - Half Magic ) decides to re-start his old alliance with Max. It did not work out well for them in Season One, but
Max ( Jessica Parker Kennedy ) arranges for Rackham to go after the Urca's treasure. However, there are other women in the intelligence-gathering business. Max's predecessor as Madame is keeping an eye on her successor, and Eleanor Guthrie is behind it all.
Silver (Luke Arnold - Half Magic ) gives Flint's crew a good pep-talk to keep the crew sharp. But his co-conspirators are not good at keeping secrets. This could get messier than Silver wanted.
Flint's hostage seems somewhat ungrateful towards her rescuers. She is deeply prejudiced against pirates, even though they are merely sailors. Since Flint is chief among them, he gets the blame. It turns out that her father told her about Flint, specifically about an assassination he was accused of in Black Sails [Season 1, Episode 4] IV.. Miranda Barlow ( Louise Barnes ), who is known as a friend of the girl's father, does not rate a mention in the journal.
Eleanor is quietly enraged at the fate of her father. It was a declaration of war, and she has a plan of her own. Not merely against Charles Vane, but against all the pirates.
Flint and Miranda try to negotiate with the Governor of the Carolinas. Unfortunately, the Governor's officers do not seem eager to make a deal.
Silver tries to cover up his conspiracy. But he has bigger things to worry about - Vane tries to take Flint's ship. How Vane got his entire crew all the way from the fort to the Carolinas is not explained.
Eleanor tries to make an alliance with the plantation owners. This sets the tone for the next few Seasons. We have seen a few black people in the background, serving drinks in the tavern, but they do not yet have names or dialogue. The institution of slavery, and the runaway slaves' fight to abolish it, will be a central premise in the following Seasons.
Flint is about to be hanged. But just like villains in the James Bond series, the Governor and his lackeys decide to draw out the proceedings. It is not enough merely for justice to be done - it must be SEEN to be done. As a result, they make it a public spectacle with long speeches about Flint's alleged crimes.
Vane has come to his senses, and instead of settling for petty revenge he wants to save Flint. Billy Bones gives him the one thing he needs to mount a public defence of the accused man. Of course, nobody seriously believes it will be a fair trial so Vane also takes a small army of cut-throats with him.
While Flint and Vane get a violent climax to their storyline, Billy Bones and John Silver are stuck as prisoners aboard their own ship. Their captor seeks to double-cross his own Captain, but to make off with the ship he will need Silver's cooperation. Silver has won the support of his own crew, but will he once again betray them to save himself? We get to learn how he lost his leg ...
Back in Nassau, the local businessmen panic when they hear Elenor Guthrie is gone. Max takes the opportunity to scrape together all the petty cash she can find and buy the businesses at a knock-down price. This will tide her over, until Rackham gets back with the Urca gold.
The story starts with the introduction of a new character - Teach (Ray Stevenson - Punisher: War Zone ). He has retired from high seas piracy, but he is still a very dangerous man.
Captain Flint is back in command of the Walrus, his ship from Season One . Rackham and Bonney recovered it when the got the Urca's gold. Now Flint is on a vengeance quest up and down the coast of the Carolina colony. He will murder any magistrate who passes a capital sentence on someone accused of piracy, and the town will be looted and burned. Silver is unhappy about Flint's mental down-spiral. Will anyone bother trying to rescue Eleanor Guthrie ( Hannah New ), last seen being carted off to face trial in London?
Jack Rackham is now the power in Nassau, and he has sent Vane out to do his bidding. They target a ship supposedly loaded with lumber, for use to repair the fort. Instead it carries slaves, who might be useful as labourers once they are freed. This is one of the first references to slavery in the show, but it will not be the last.
Jack needs the slaves because he cannot afford to pay pirates to do the work. The presence of the Urca's gold has caused massive hyperinflation in Nassau, which means the local economy is screwed. There is no way they can secure the fort, which means they cannot brotect the gold they spent two Seasons chasing.
The Walrus is on the way home to Nassau when they discover a ship floating alone without a crew. Flint reluctantly stops to investigate.
The British Government has taken a few steps to end piracy. They have sent a Royal Navy hunter to give chase, commanded by an experienced sea-captain who used to be a pirate. They have also assigned a new Governor, Woodes Rogers, to New Providence Island. And he visits Eleanor in her cell to ask for advice.
The Walrus has entered a storm in order to escape the Royal Navy hunter. This is a hell of a risk. While Flint does derring-do above-decks, Silver is stuck underneath trying to caulk ruptured timbers. This is not a good place to be, when the bilge fills with water and they are trapped under the deck.
Jack is making progress with repairs on the fort. Max advises him to split the risk, by swapping the gold for something of equal value but lesser volume - like pearls or gems.
Eleanor gives Woodes Rogers the datails of her astonishing rise to success. When put in charge of Nassau at the age of seventeen, she had to remove Edward Teach from power. To do this she co-opted his key rivals - Benjamin Hornigold and Charles Vane. Ironically, those men are all key players in the new fight for Nassau.
Everyone believes the Walrus was sunk in the storm. However, it has been becalmed in the doldrums of the Sargasso Sea – and there is not enough food for everyone. They try fishing, but all they can catch is a few eels. Flint plans on sacrificing the less-useful members of the crew - not was worship to a pagan god, but just to make the food last longer. Unfortunately Flint is still suffering severe PTSD from the loss of his lover. Silver tries to bond with him, by making Flint treat him as an equal. This involves making a risky confession.
Eleanor acts as an unofficial advisor to the Governor. Back in Nassau, it is Max and Anne Bonney who are in charge of fencing the stolen gold. Yes, in a show about male pirates it is women who make the big decisions.
Max gets word from a merchant about the Royal Navy's fleet on its way to invade Nassau. Rackham tries to organise the defences. Teach has somehow gotten word about Flint and Hornigold. Yes, everyone except Rackham knows what is going on in the world. Anyway, Teach offers to take Flint's role as commander of naval defence forces - in exchange for Vane agreeing to rejoin his crew.
The Governor's ploy, thought out by Eleanor, has worked. Certainly for her, since she gets promoted as a result. Teach and Vane did not dare to fire on Hornigold, certainly not while under a flag of truce, and the offer of pardons has convinced many of the men there. In fact, everyone except Vane's crew wants to turn him in for the ransom. In contrast, Vane's crew only want to keep the fort and the gold.
The Walrus has reached dry land, but the island is not uninhabited. Flint and his crew end up in the hands of the locals, an army of escaped slaves who live in a spectacular Ewok-style village. Silver tries to seduce the Queen's daughter, while Flint and the others are locked up with Ben Gunn.
Teach and Vane try to break out through the Royal Navy's line. They have a plan, and the advantage of suprise. However, the Governor is a former privateer who knows how to fight a sea battle too.
Vane and Teach set off to catch a Spanish merchant ship. Previously the Spanish ships were regarded as off-limits, to avoid any counter-attack against Nassau. After all, despite being technically a British colony the pirates wanted to be neutral in the war between the two Empires. Strangely, even after the seizing of the Urca treasure the Spanish have not risked openly moving against Flint and his colleagues. Perhaps they have a more subtle strategy.
The Governor tries to set things up in Nassau. Eleanor visits Max, her ex-lover who eventually replaced her. It turns out that although Max got a pardon, just like the other pirates, her criminal history means she has been denied a role in the town council. Max decides to bribe the Governor with her share of the Urca gold. Elsewhere, Rackham and Bonney make off with their own share, a literal cart-load of treasure.
There is a lot of unmasking this episode. One character was the secret King of the runaway slaves. Another has secretly been a spy for the Spanish Empire. Before this episode, those factions had not exactly been major player.
The Governor, Woodes Rogers, was in fact a very interesting if somewhat obscure historical figure. He captained the ship that rescued Alexander Selkirk, which inspired Daniel Defoe to write Robinson Crusoe. This book in turn inspired Robert Louis Stevenson to write-in Treasure Island - specifically the character of Ben Gunn, Flint’s mutinous castaway. So this real-life person is now appearing in a story based on a fictionalised version of his own life.
Rackham and Bonney now sail under Captain Edward Teach (Ray Stevenson - Rome ).
Captain Flint (Toby Stephens - Die Another Day ) and Billy team up to liberate a slave plantation. Flint has a team of escaped slaves, while Billy has the loyalty of the pirate crew. Unfortunately they have different ideas on how to achieve their goals.
John Silver (Luke Arnold - Half Magic ) is now in the custody of Israel Hand, a vicious killer who was expelled from Blackbeard's crew.
Max ( Jessica Parker Kennedy ) is now an important businesswoman in Nassau. Once this show was all about the topless whores. Now, like the later Seasons of Game of Thrones , the focus is less on the sex and more on the politics.
Eleanor's departure is delayed because the redcoats are needed elsewhere. Their commander has decided to search the wrecks on the beach, because his spies have told him that Silver is hiding out there. Max also carries the blame, for playing both sides. But the redcoats have forgotten about Flint and his army of rebellious slaves.
Blackbeard (Ray Stevenson - Punisher: War Zone ) and his men come off the worse in a fight with the Governor. Well, he might be good against relatively unarmed merchant ships but it is a different thing to board a ship with a garrison of redcoats aboard.
The Pirates control the town again, but Eleanor is still in command of the fort. The only thing she cares about at the moment is protecting Max, who has gone missing in the confusion.
Rackham and his crew are in the hands of a sadistic madman. Anne Bonney has a plan to escape.
Eleanor seems to be keeping her side of the bargain. Her husband is reluctant to take his ship away, but he has no choice. So instead he starts to think for himself. Since the British Empire is not able to help him, he instead turns to the Spanish. They both support a Royalist, Imperialist system ... as opposed to Captain Flint and his Leveller sympathies. Yes, this is not about Brits versus Spaniards - it never has been. It is class warfare, Anarchists versus Imperialists.
Billy does not want to keep the deal with Eleanor, and is more than happy to sacrifice Captain Flint. Yes, this has become double-cross after double-cross.
Rackham is less than happy to discover Flint's deal with Eleanor, in which he bought the fort from her with Rackham's share of the Urca treasure. In fairness to Flint, there are no pockets in a shroud and money only has value if you can spend it. But Rackham knows what Rogers did to Teach, and knows that Rogers will never allow himself to be defeated by the pirates.
A dozen Spanish ships and a thousand Spanish soldiers attack Nassau town. Governor Rogers told his Spanish rival to burn everything to the ground, and the soldiers seem to have taken that literally. Better dead than red ... white and blue. The good news is that it would not be practical for them to bring cavalry.
Silver tries to negotiate an alliance with the rebel slaves. However, the slave leader points out that Pirates' loyalties shift quickly and easily. This is the problem with democracy - instead of a monarchy which can provide decades of stability, an elected ruler will only remain powerful as long as he is popular.
The Governor seems broken by Eleanor’s fate. But he has one last hope for revenge. One of the prisoners is Billy Bones, who likewise wants revenge on Flint and Silver. Another prisoner is Silver’s lover, believed by all to be dead. Somehow she survived her injuries, and the inferno, despite Eleanor’s belief in her failure … and Flint’s search of the area. Anyway, the Governor ransoms her … with the intent of splitting the pirates’ alliance.
Rackham accepts Max’s plan, and sails to Boston. He tries to make a deal with Eleanor’s grandfather, whose family bankrolled the pirates of Nassau for many years. Unfortunately Grandpa is now working for the Quakers of Pennsylvania, and now must distance himself from all such immoral issues. However, Grandma is a different matter. And Max, as an experienced businesswoman who was involved in all commercial interests in Nassau at one time or another, can save the day.
There is one problem with the deal. In order to ensure it is business as usual, Flint must be disposed of. Similarly, Silver has a plan that might ultimately involve killing his partner. And since one of the few things we know about his this story ends is that Flint dies before the events of Treasure Island , it seems inevitable that sooner or later one of them must get lucky.
Billy's plan is to drive Flint and Silver apart by making them fight over the treasure. He tells the Governor to lure them to a remote island. Yes, finally everything to set up Treasure Island is being put in place.
The Governor has other problems. If he is caught ransoming slaves to the pirates, he will face a mutiny by his own men. After all, his subordinates have agendas of their own. Meanwhile, with Max and Eleanor out of the picture the Governor's new woman and the brothel's former madame conspire together.
Anne Bonney and Max are still in Boston. Anne Bonney is still recovering from her wounds. She gets a lecture from one of Max's whores about what she did to Charlotte in Season 2 . Nobody can say that this show does not pass the bechdel test. Max has Grandma Guthrie to show her the ropes. The plan is for Max to marry a rich local gentleman, who can be their pawn as the next Governor of Nassau. But will Max do the right thing?
Rackham has a lot to deal with. He will have his work cut out for him, killing Flint to keep the bargain with Guthrie. But if he steps back and lets Woodes Rogers do it first, this means losing the treasure and thus control of Nassau. This is a winner-takes-all game he must take both the treasure and Flint's head to win.
Flint has taken the treasure chest to Skeleton Island, and is trying to find somewhere to hide it. Silver sends his best six men inland to recover the treasure. Of course, Flint is worth at least ten other pirates. Silver knows this, and lands to command the search in person. Anyway, the question is raised - do main characters become more survivable simply because they have dialogue, or are they given dialogue because their skills make them survivable?
In flashbacks, we see Flint teach Silver the art of swordplay. Silver points out that if Flint teaches him how to win, he will thereby be teaching how to defeat Flint himself. In return, Flint points out that Silver has still not revealed his origins. In all the years they have known each other, Silver has not told anyone his true identity.
Rackham and his shipmates are relying on a navigator who is incredibly old. Will they be able to find Skeleton Island if he dies on them?
Billy Bones urges the Governor to make his move. They do not care about the treasure, merely about destroying the pirates. And now, with Flint and Silver at each other's throats, the pirate ship's crew is at a severe disadvantage.
Flint and Silver's ship is gone. Luckily Rackham arrives just in time to unite the two main storylines. They give pursuit to the Governor's ship, and attempt to seize it with a boarding action in order to save the hostage.
There is a breathtaking duel between Flint and Billy, in the rigging at the top of the front mast. Real swashbuckler stuff. But the real climax is a lot more low-key. Flint and Silver face off against each other in a simple conversation, as each bares his soul to the other.
Back in Boston (or is it Philadelphia?) Rackham is reunited with Anne. He and Max offer a new deal, a compromise. Will Flint and Max get a happy ending? Will one end up in a happy gay marriage, and the other getting the political and financial power they crave? In a story like this, nobody can have it all.
The ending ties up all the loose ends