|Title|| Royal Navy Lieutenant (formerly)|
Spanish Man O' War
|Relationships|| Hal Gates (Quartermaster, deceased)|
Billy Bones (First Mate/Enemy)
John Silver (Quartermaster/Friend)
Miranda Barlow (Lover, deceased)
Thomas Hamilton (Lover)
Hennessey (Former Superior Officer)
Charles Vane (Enemy/Ally/Friend; deceased)
Eleanor Guthrie (Friend; deceased)
Jack Rackham (Rival/Ally/Friend)
Anne Bonny (Rival/Ally/Friend)
Edward Teach (Enemy/Rival/Ally; deceased)
Woodes Rogers (Enemy)
|Appearances|| First: I.|
|Portrayed by||Toby Stephens|
|Gallery||James Flint Gallery|
- "England has shown herself to me; gnarled and grey, and spiteful of anyone who would find happiness under her rule. I'm through seeking anything from England except her departure from my island. "
- ―James Flint to Woodes Rogers[src]
James McGraw, better known as James Flint, is a pirate captain in the Caribbean, known throughout the West Indies as one of the most feared of all the Golden Age pirates. Originally a lieutenant of the Royal Navy, the death of his lover and his own personal disgrace in England drives a simmering rage in him, and a propensity towards breathtaking violence. In order to hold off the civilisation, he will make himself ruler of Nassau through any means necessary. To accomplish his goals, he started the hunt for the Urca de Lima, the richest Spanish treasure galleon in the New World.
At the end of the series, he survives at the final battle and is finally reunited with Thomas Hamilton, his lover who believed dead long time ago.
Most of Flint's youth is shrouded in mystery. He is the son of a carpenter and his family was not well off. His real name is James McGraw. Once a Lieutenant in the Royal Navy, he served under the command of Admiral Hennessey. In 1705 he met Thomas Hamilton, an aristocrat who wanted to clean up piracy in the Bahamas and make New Providence Island a British colony. He began an affair with Hamilton, and people thought the affair he had was actually with his wife Miranda, with whom he was also having an affair. Thomas's political enemies exiled him and "made Thomas disappear" using the affair as an excuse. Flint went to Nassau with Miranda to finish what Thomas started.
Flint the Pirate
Once he reached New Providence Island, Flint quickly became the captain of a crew, having met Hal Gates in a tavern and persuading Gates and his crew to let him lead. He eventually became captain of the mighty Walrus. Over the next ten years, he became the most successful pirate on the island, bringing to Nassau more booty than all other pirate captains.
He maintained the relationship with Miranda Barlow, who also settled on New Providence. However, stories soon arose among Flint's sailors about Miranda being a witch who has enslaved Flint to do her bidding. On one occasion, Flint and his crew followed the merchantman Maria Aleyne for months, believing that her cargo was worth a fortune. However, when the pirates boarded the merchant ship, they discovered that the booty was much smaller than they expected, and some of them noticed that Flint had slain two unarmed passengers, and later gave report about their deaths to Miranda. It was later revealed that the reason the Maria Aleyne was targeted was because she carried Lord Alfred Hamilton, whom Flint desired to kill in revenge for the death of his friend and lover Thomas, and for his and Miranda's own exile.
In 1715, Flint was leading an attack against an unnamed merchant ship. As his crew is butchering the merchant crew, he exhibited restraint by calling an early stop to the slaughter. Taking control of the ship, Flint went to the captured captain's quarters in search of the shipping schedule of the Urca de Lima. To the dismay of Flint and his quartermaster Gates, the page had been torn from the book.
In the Captain's quarters, Gates informed Flint that he believed Singleton was very close to having enough votes to depose Flint from his captaincy. Gates stated that the crew were desperate for larger prizes and felt that Flint is no longer effective. With the schedule seemingly lost, Flint told Gates that he planned to get a copy of the schedule from Richard Guthrie, the chief black market merchant in Nassau.
With the Walrus' Boatswain Billy Bones accompanying him, Flint went to Guthrie's mansion and requested an audience with Guthrie. At the meeting with Guthrie, Flint told him about his desire to capture the Urca de Lima and about his pursuit of the missing schedule. The meeting was interrupted by several members of the British Royal Navy, led by Captain Hume of the Scarborough. This lead to a confrontation where Guthrie was shot in the shoulder. Flint decided it was best to take the wounded Guthrie to the Walrus.
Once aboard the ship, Gates told Flint that it was time for the vote. Before the vote, Flint retired to his cabin for a moment, where he discovered a white feather that had been placed in a drawer as an alarm. Realizing that it was likely that a member of his own crew had the schedule, Flint devised a scheme that would hopefully help him defeat Singleton. Flint accused Singleton of having undermined their effort to capture the treasure ship by stealing the schedule from the logbook. The two men then engaged in a duel. During the sword fight, Singleton initially had the upper hand but once Flint struck Singleton across the face with a small cannonball, the tide turned and Flint beat Singleton to a bloody mess.
Still hovering over the defeated Singleton, Flint pulled a piece of paper from the clothes of Singleton and handed it to Bones. Bones opened the paper and saw that it was blank. Bones' loyalty was effectively being put to the test by Flint handing him the paper. Bones could either expose Flint for being a liar or could claim that it was the missing schedule, exonerating Flint. Bones chose to stick by Flint and told the crew that it was indeed the missing schedule. Flint then pumps up the crew when he, for the first time, was honest with them about his mission to capture the Urca de Lima. He claimed that the ship was of such value that it will make them "princes of the New World".
Despite winning the duel, Flint still had a bigger problem on his hand: finding the stolen schedule. He eventually realized that it could only be one member of his crew: the cook John Silver. Flint chased Silver to the shore and eventually came to find out that Silver was planning on selling the schedule to Charles Vane and Jack Rackham. Flint would eventually catch Silver and was horrified to find out that Silver had burned the schedule, but had committed it to memory.
Flint ended up taking the wounded Richard Guthrie to the house of his lover, Miranda Barlow, for recovery. He asked Miranda to take care of Guthrie while he went about preparing for the expedition against the treasure ship. In Nassau, Eleanor Guthrie promises to finance the expedition. Flint must find a second ship to accompany him and it was determined that the best choice would be the Ranger, Charles Vane's ship. However, before they set sail, Eleanor blacklisted Vane and made much of the Ranger crew switch to Flint.
Before they set out on the expedition, Flint requested bigger guns for his ship. Eleanor promised that she would get them from the merchant ship the Andromache. When Eleanor is betrayed by her father Richard, the Andromache left port with her guns still aboard. Flint decided that he must chase after her to get the guns for his expedition. When Flint eventually caught up with the Andromache, he boarded her but found out that her captain, Dyfed Bryson had alerted the Royal Navy ship Scarborough of her location in anticipation of Flint attacking her.
As the crew of the Walrus struggled to find a way into the Andromache's hold where Bryson and other members of the Andromache crew were hiding, Flint appeared to be losing a slight grip on loyal members of his crew such as Logan, who openly questioned Flint's decision to stay aboard the Andromache as daylight approached and the Scarborough drew nearer.
However, Gates once again displayed his loyalty by punching Logan in the face and reminding the crew of their sworn duty to follow Flint to the death in battle. Eventually, after retrieving the guns from the Andromache and attempting to escape, Flint realized that a mast from the Andromache had broken off and gotten tangled with the Walrus. While Flint and Bones struggled to free the ship from the broken mast, Flint questioned Bones about a letter that Bones had found in Bryson's cabin from Mrs. Barlow. Before Bones could say anything about the content of the letter, he was swept overboard and was presumed dead. After they are safe, the crew hold a funeral as sea for the men who died, with Captain Flint presiding over it.
After returning to Nassau, Flint met up with Eleanor and discussed the changes to the islands leadership while he was gone, and bring up the fact that her father was responsible for the trouble Flint went through getting the cannons. As he was heading out, Eleanor pointed out to him that Silver had been of help to Eleanor and that she promised him that she would inform Flint not to kill him once he was done assisting him.
After the meeting, Flint returned to the Walrus and was cornered by Gates in his office. Gates questions Flint about the letter Billy found before his death, and then questions Flint on the matter of Billy dying really being an accident. When Gates tells Flint that he is going to tell everything about the letter and Bones to the crew, Flint stops him and admits that he is taking the prize money for himself. He states that he is going to put the prize money in a warehouse and then sequester a portion of it away from the crew. He says that he knows the crew will just drink, whore, and piss all their money away. He wants to keep a portion to be used for creating a safe place for the men to live in. Gates finally states that he will sail with Flint to take the prize, but after that, they are done working together.
When the Urca turns out to not be where she is supposed to be, Flint decides to nevertheless attack a Spanish Man'o'War that has come out of nowhere, for he believes that it is the consort of the Urca de Lima. When Gates questions this line of thinking, Flint strangles him and kills him. When Flint attempts to attack the Spanish Man'o'War, he is stopped by Dufresne, who begins a mutiny against Flint. Flint is then shot by Dufresne when he tries to fire one of the ships guns on his own. The subsequent battle goes against the Walrus and she is beached, having nearly been destroyed by the Spanish ship. When he woke up, Dufresne showed him the Urca broken in half on the nearby beach, and the soldiers from the Man O' War collecting the gold.
Now stranded on the shores of Florida and removed from captaincy, Flint explained to his former crew that their only chance to escape was to capture the Spanish warship, because the majority of her crew was on the beach. In exchange for a pardon for his crimes against the crew, he volunteered to be one of the two who would swim to the ship and kill the guards. John Silver agreed to join Flint. Once they got aboard the ship, Flint and Silver managed to kill all the guards, but they were captured by other members of the Spanish crew. Silver seemingly betrayed Flint but then saved his life. The pirates then attacked and took over the ship, sailing for Nassau. Later that night, Dufresne told Flint that once the ship reaches Nassau, he and Silver would have to leave the crew.
However, during the journey, Flint advised Dufresne not to attack any merchant ship until they get more recruits. When Durfresne did the opposite, the crew of the attacked merchant ship resisted the attackers, and Flint ordered the pirates to open fire. Later, the crew voted to have Flint reinstalled as captain.
Once the ship reached Nassau, Flint and Silver went ashore to ask Captain Hornigold to join them on their journey to the Urca's wreck, as they would need at least one more ship to defeat the Spanish soldiers who guarded the treasure. To their surprise, they saw Hornigold's pirate flag flying over the small shack and not over the fort as they had expected. Flint learns that Vane has taken over the fortress, and must be dealt with before he can safely bring the Urca gold back. He demands that Eleanor do something about Vane, but he worries she cannot be trusted.
Hornigold and Flint’s crew join forces to neutralize the threat posed by Vane and his fortress. They send a messenger to Vane, ordering him to abandon the fort before dawn, or the warship will attack. With information from Hornigold, they moor the Man O’ War where the fortress cannot place its batteries. When Vane tries to turn the unaffiliated pirates in Nassau against him, Flint sends Silver ashore to persuade the pirates against Vane. Whilst ashore, Silver learns that Billy Bones actually survived being dropped into the sea. Silver is reluctant to let him speak to the crew, fearing Flint intentionally dropped him, but Billy says he has seen the size of the British forces and believes that Flint is the best hope for Nassau.
Before dawn, Flint opens fire on the fortress, eventually breaching its walls. Flint calls for a cease-fire and commands that the men move ashore to storm the fortress. On shore, Flint encounters Mrs. Barlow who demands to speak to him. Unbeknownst to Flint, Eleanor had visited Mrs. Barlow, to try and make Flint soften his stance. In the parlour of Eleanor’s tavern, Barlow informs Flint that Vane has captured Abigail Ashe, and that Flint needs to take her from Vane, and return her safely to her father in Charles Town, in return for pardoning all the pirates of Nassau.
Flint is still considering this plan of action, when suddenly Vane springs from somewhere in the room and attacks him, having sneaked out of the fortress. The two men trade blows with each other until they are interrupted by Eleanor with a musket. She forces the men to talk. Flint offers to stand his men down from attacking Vane’s fortress, if Vane will give him Abigail Ashe. Vane demands the Spanish Man O’ War in return. Flint is reluctant, but Eleanor assures him that Vane will agree to the terms without the Man O’ War.
When Hornigold learns that Flint plans to allow Vane to keep the fortress, he challenges Flint for captaincy of the combined crew. Just before the vote is to take place, the men left to spy on the Urca gold return, claiming that the Spanish returned and took every piece of gold off the beach. Hornigold’s faction completely fades away. Flint persuades Silver to convince the men to continue to go along with the plan to return Abigail to her father. Although, they lose some men, most of the men remain with Flint, who retains captaincy.
Flint is summoned to the tavern where he finds Abigail, who Eleanor has sneaked out of the fortress after betraying Vane. He introduces himself as James McGraw and a friend with her family. As Flint’s ship sails to Charles Town, Abigail warns Flint and Barlow that her father has changed from a reasonable man to a hater of pirates, because Flint murdered of Alfred Hamilton.
Flint and Barlow take Abigail ashore requesting only to speak to Peter Ashe. When Ashe’s subordinate, Colonel Rhett, sets upon Flint, Abigail intervenes and demands that they stop, explaining that Flint is an old friend of her father’s. Flint and Barlow meet with Peter Ashe to discuss Flint’s proposal for a reconciliation between England and the pirates of Nassau. Ashe is reluctant, but Flint encourages him to ask any questions and promises he will be truthful in answering. When the subject of Alfred Hamilton is brought up, Miranda admits that she is the one who arranged his murder. Flint then asks that Ashe not judge him for his past deeds and instead offer him redemption. While they are talking, Miranda’s attention is diverted to the chiming of a grandfather clock. Ashe eventually agrees to consider the plan.
Ashe finally states that he has given the plan much thought, and the only way for it to work is that they both return to London together where Flint will confess his crimes and ask forgiveness from Parliament. Flint agrees. Just then, Miranda realizes why the clock is so familiar to her: it belonged to Thomas and was in their home in London. Ashe admits that it was a gift from Alfred Hamilton. It is then revealed that Ashe was the reason behind all of their misfortune, and betrayed them in return for the governorship of the Carolinas. Miranda becomes increasingly aggravated and says she would like Ashe to take responsibility for ruining their lives. Suddenly, she is shot through the head and killed by Colonel Rhett. Flint tries to attack Rhett, but is subdued and knocked out by Ashe’s men.
Meanwhile, Charles Vane has made his way to Charles Town, captured the Man O’ War, and taken Flint’s crew captive. However, Silver sabotages the ship delaying their departure, for which the Vane’s crew cut off his leg in revenge.
Flint is put on trial for piracy in the town square in Charles Town. Ashe asks Flint to confess to his crimes so that he can be executed privately and not in front of a jeering crowd. Flint calls him a coward. As the prosecution continues, it is interrupted by the arrival of Charles Vane. Vane states that he wants to be a character witness for Flint by reading from Abigail’s diary. However, this is a ruse for an escape plan. While the diary is read, Vane’s men climb up the walls of the city, take out the gun crews, and turn the cannons on the town. During the chaos that ensues, Flint confronts Peter Ashe and stabs him through the gut, mortally wounding him. Flint and Vane then fight their way to the jetty and begin to escape on a rowing boat. As Colonel Rhett and his men prepare to fire at the rowing boat, they are killed by artillery fire from Flint’s ship. Once Flint and Vane make it back to the ship, Flint orders that all of the men be released and opens fire indiscriminately on Charles Town.
Sometime later, Silver awakens inside the captain’s cabin. Flint informs Silver that he has been elected as the ship’s quartermaster. Silver then lies and tells Flint that Vincent had confessed to him that he had lied about the situation with the Urca gold and had sold the information to another crew.
In the months following the events of Season Two, Flint, Silver and the Walrus crew have continued their reign of terror, raiding towns along the Carolina coast and killing magistrates who hang pirates. Silver as Quartermaster is struggling to control Flint’s increasing recklessness. Flint meanwhile is having recurring dreams of his dead lover Miranda.
On the journey back to Nassau, they spot pirate Captain Hallendale’s ship drifting. Silver insists on investigating despite Flint’s reluctance. Onboard, they find it completely empty, save for the corpse of Hallendale. They realize to late that it is a trap, when they spot a powerful Royal Navy hunter in the distance. As it approaches, they are shocked to find Captain Hornigold, former pirate turned pirate-hunter, who offers them all pardons.
Flint convinces the crew to reject the pardons, and escape into a terrible storm. In the midst of the storm, De Groot warns Flint that the ship will sink unless the topgallants are cut away. Flint finally grabs an axe and personally cuts them away, leading to the death of several crewmen.
When the storm subsides, the Walrus is becalmed. Flint becomes increasingly tyrannical, dividing the crew into critical men who will be fed, the others not. He also casually executes two men accused of stealing food. During a trip to investigate a dead whale, Silver uses his smarts, and reveals how he deceived Flint and stole the Urca gold. He finally wins Flint’s respect, and his audacity is rewarded with the return of the wind.
The wind drives the Walrus to an uncharted island. As the crew recuperate, Silver and Flint consider all the pardons Hornigold offered, with Silver fearing it is the prelude to an attack on Nassau. If so, Flint fears the battle is likely already over. However, they are interrupted by a large force of well-armed ex-slaves. The whole crew is taken at gun point, through a trap infested forest, to a large settlement and imprisoned.
Billy Bones, Silver and Flint all deal with the direness of their plight in their own way. For Billy, he wants to escape through the trap laden forest. For Silver, he’ll talk his way out of it. And Flint, he doesn’t know if he has any more fights left in him.
All seems lost until the wounded “away” Maroon King, Mr. Scott, arrives from Nassau. Flint is granted a private audience with the gravely injured Mr. Scott, and learns that Nassau has fallen in Flint’s absence. Mr. Scott is in favour of a partnership with Flint, now that they cannot be supplied from Nassau. However, the Maroons Queen has the final say. Flint is called before her to discuss a proposed partnership. With Silver’s help, Flint polishes up his sliver tongue, and speaks honestly. He tells her that together they can take things back, starting with Nassau. A partnership is agreed.
Flint goes to seek new allies, especially Charles Vane. He tracks Blackbeard and Vane to Ocracoke Island. Flint wants Vane to rejoin him in retaking Nassau, and bring the fleet with him. Teach refuses to step aside lightly. To decide the matter, Flint and Teach choose to duel. Teach wins the duel, but before he deals Flint a deathblow, Vane steps in, having finally made his decision regarding his loyalty. Vane fights off Teach to the point that Teach lays down his sword and orders them both off his island.
Vane convinces Flint to go after the cache of pearls that Rackham and Bonny have secured, and while in Nassau recruit new men. To prevent Flint picking up the new recruits, Governor Rogers himself waits for him on the beach. Flint goes ashore and the two men feel each other out. Woodes tried to appeal to Flint's past, saying he is finishing what Thomas Hamilton started. However, Flint argues that he went to Charles Town to make peace with England, and Miranda Barlow was killed for it, so now he won’t stop fighting to remove England from Nassau. In the end, Rogers decides to stop the pardons, from now on the pirates will be hunted and hanged. .
They finally learn that Rackham has been arrested, and that Bonny is to be tricked out of the cache. Vane convinces Bonny to give up the cache, so that they can ambush the convoy taking Jack and the cache to the Spanish. They learn the convoy route through the prostitute Idelle, and swiftly attack it on horseback. After killing all of Rogers’ soldiers in the convoy, Vane shoots the wheel of the carriage sending it careening off the road. Jack is banged up pretty badly, but alive. Vane urges Flint to take the pearls and go ahead, while he frees Rackham from his chains. However, more of the Governor’s men approaching, and Vane is eventually outnumbered and arrested.
Flint, Rackham and Bonny are picked up by Silver and the Walrus, while Billy goes to Nassau to try and free Vane. However Hornigold is in pursuit, and follows the Walrus back to the Maroons Island, where Flint and Silver pull a daring move to turn the ships broadside on Hornigold. With a small army of ex-slaves on the beach, Hornigold is forced to fall back. Flint informs the Maroons Queen that they now have a week to prepare for the English attack.
On the eve of battle, while Silver, Flint and Rackham are burying the cache of pearls, Silver learns the truth about Flint’s tragic past. Afterwards, Silver surmises that although those closest to Flint often die tragically, he himself might actually be Flint’s successor.
Flint leads the defence of the beach against overwhelming English forces, and then falls back into the forest. Despite Flint’s objections, Silver gives Dobbs a key role in the ensuing battle, as proof that he is both loved and feared by the men. Dobbs pretends to betray Flint and leads Hornigold and the English soldiers into an ambush. Flint’s concealed men leap out and begin slaughtering the English soldiers. In the ensuing chaos, Hornigold kills Dobbs, but then Flint shoots Hornigold fatally in the chest and proudly stands over his dying body. Soon, the English soldiers are forced to retreat, with Flint defiantly calls after them.
Meanwhile, in Nassau, Billy Bones stirs up rebellion and creates a new bogeyman for the governing powers to fear; not Flint, but Long John Silver.
After their victory on Maroon Island, Captain Flint sets his sights on retaking Nassau. As they approach, Flint worries the fragile alliance won’t hold, but Silver reassures him; he hasn’t considered murdering him in months. What was supposed to be an invasion of overwhelming force, only ends in disaster. Rogers continues to demonstrate his cunning by sinking ships as a hidden blockade. Most of pirate fleet run aground within range of Nassau’s cannons and bloody carnage ensues. Flint orders his men to abandon ship.
On an isolated beach, Flint and Madi watch dejectedly as the last bedraggled pirates reach their rendezvous, with no sign of Silver. Soon, Billy Bones arrives and leads them into the interior where his pirate rebels hold out. However, things between Billy and Flint quickly turn tense with Billy refusing to allow Flint to dominate the pirate alliance. Flint faces off against Billy, holding the location of the Urca gold over Billy’s head. However, Madi corrects him; she also knows where the treasure is, from Silver who is now her lovers.
They do agree to raid on the Underhill plantation to liberate its slaves and bolster their manpower. However, there’s a snag; to protect their assets, the loved-ones of the slaves have been spread among all seven plantations on the island. Flint orders a tactical retreat, but Billy’s lingering resentment blinds him to fact that it's the right choice. Before we know it, the raiding party is split in half, and taking swords and pistols to each other. In the end, Billy and his remaining men retreat anyway as the local militia arrive.
Afterward, Flint and Madi reassert their alliance, blaming Billy for the debacle. When Madi learns that Silver is alive, Flint goes find him at Israel Hands’ hideaway, and save them from the redcoats hunting them. Meanwhile, Captain Berringer lays on the hanging of the captured pirates with full public spectacle to draw Silver into a trap. Silver rides into Nassau flanked by Flint and Hands, but Berringer is ready with his redcoats. Inspired by their Pirate King, the townspeople join the revolt. Nevertheless, it looks like the redcoats have the pirates down, when Billy and his men show up in the nick of time.
With the pirate taking over Nassau, Flint organises a new Captain’s Council, but it’s Silver’s word that rules, though for now they’re of one mind. Later, Eleanor holds a secret meeting with Flint and Silver to strike a deal to surrender the fort in exchange for Urca cache. Silver immediately refuses, but watches helplessly as Flint accepts the deal, offering himself as guarantor.
After Eleanor drives off her husband Rogers, Flint and Eleanor emerge from a tunnel under the fort, where Madi’s people are waiting to make the exchange. They lead them to a secluded beach, but the only thing waiting from them is Jack Rackham with a small crew; the ship that was seen approaching was Rackham’s and not the one sent to retrieve the cache. Jack is horrified at the deal; having seen Rogers for the man he truly is, he’ll never accept such a deal.
Trying to return to the fort, they find Rackham was right, with Nassau in the throes of a devastating Spanish invasion incited by Rogers. Flint, Eleanor, Madi and her men are holed up at Mrs. Barlow’s abandoned house, when they spy a small band of Spanish scouts. As the Spaniards approach, Flint and the men kill everyone except for three Spanish soldiers who flee. Leaving two men behind, Flint and the others give chase and kill them. However returning to Miranda’s house, Flint finds it completely ablaze with only Eleanor seemingly having escaped. Flint holds her in his arms but she’s dying. In her final moments, she asks him whether Rogers is the reason the Spanish sacked Nassau. Flint knows full-well that Rogers is the cause of this, but does her the kindness of lying.
Flint finds Silver on the Underhill estate after the pirates and slaves drive off the Spanish, and delivers the devastating news; Madi is dead. Silver is distraught as Flint orders everyone to retreat to Rackham’s ships. However returning to Maroon Island, they find it full of pirates and ex-slaves from all over the West Indies who want to join the war.
Later, Silver receives a letter from Rogers offering a deal; Madi for the cache of Urca gold. Silver, reeling from news that Madi is alive, wants to do the exchange, but Flint insists on a plan to rescue her. Silver has become weary of this war against civilization, but as they sail for Nassau, Flint assures him that they have the right people to lead them once the war is won; Silver and Madi. He could be saying it sincerely, but for the first time Flint seems like the lesser of the two.
The next day with the Walrus in range, Rogers executes the men Flint sent ashore to rescue Madi. To Flint’s helpless bewilderment, Silver orders Israel Hands to bring up the Urca cache which he had dug up in secret. Rogers weighs anchor and sets sail, with the Walrus in tow.
However arriving at Skeleton Island, Flint absconds into the forest with the Urca cache. Inevitably, Flint proves himself utterly ruthless, killing five of the six men that Silver sent to kill him and burying the cache, before Silver finally confronts him. After all that’s happened, Flint is still willing to talk-out their problems, even killing Dooley when he tries to intervene. However, Silver only sees it as Flint killing yet another man in the name of his cause. Silver attacks. The fight is short but ferocious. The only thing that saves either one is the sound of explosions; Rogers has used their absence to attack the Walrus.
Things look bad for the surviving Walrus’ crew until there’s a signal from the Roger’s ship… Jack Rackham has arrived. While Rogers heads out to sea, Rackham picks up the survivors, and grudgingly allows Flint to take command of the pursuit. As Rackham’s ship leaves the inlet, Rogers is waiting, and Flint orders him rammed. The fight occurs at all levels of the ship; Flint clashes with Billy high in the crow’s-nest, Silver searches below for Madi, while Rackham leads the men on maindeck and faces off with Rogers. After sending Billy falling once again into the sea, Flint joins Rackham’s fight. Finally outmatched, Rogers is defeated and the pirates overtake the ship.
With Madi safe, Silver and Flint go ashore to retrieve the cache. Only… Flint won’t take him to it until he clears the air. This time, Silver has something to say. He believes he’s seen Flint’s war for what it truly is: the senseless violence of a man with nothing left to lose and just wants to see the world burn. Flint bites back that sooner or later, Silver will want proof that he mattered. However, Silver is resolute and begs Flint to yield willingly.
In the end, Silver has Flint taken to the Savannah plantation where the English aristocracy send troublesome family members to be incarcerated and cared for in secret. Flint is escorted to Thomas Hamilton who’s imprisoned there; holding the man whose presumed death gave birth to Flint, the old McGraw seems to re-emerge.
Flint is known throughout the West Indies as one of the most feared of all the Nassau pirates. He's arguably one of the strongest fighters in the series, skilled with sword, pistol and even fists; he was defeated in a duel with Blackbeard only after weeks of starvation. Even Vane acknowledges him as the best naval strategist in Nassau.
Flint is very charismatic, a cunning manipulator, shrewd and ruthless. He uses fear to lead others, and is fearless himself. As captain, he distances himself from the crew, while justifying it as due to resentment of his classical education. In truth, he can be distrustful of them, and believes himself the only person intelligent enough to understand his “noble” goal - revenge against the whole of England.
His charisma masks a deep, simmering rage, and a propensity toward breathtaking violence. Nothing will stand in the way of his plan; not Billy, not Gates. His sanity grows steadily more unstable over the first two seasons, up to the point of killing his friend Gates for doubting his plan. Then after Miranda’s death, he snaps, having a massive freak out, until Silver gets him in check again.
Flint's partnership with Silver works better than any of the others, as Flint respects him, trusts him, and even considers him a friend. However, the partner-turned-friendship is truly tested over Madi. Ultimately, the history of people being irresponsibly consumed by Flint's crusade - Gates, Eleanor, Miranda, countless crewmates - and the prospect that the woman he loves will be next, is too much for Silver. He betrays him and sabotages his war against civilisation.
- Flint is a fictitious character created originally by Robert Louis Stevenson. In Treasure Island, he died a few years before the start of the book. Given the series is set twenty years beforehand, don’t expect him to die anytime soon.
- His first name is revealed as James in Miranda Barlow's letter to the authorities in Massachusetts.
- He has a tattoo of a crescent moon on his right arm.
- The surname McGraw derives from the last name that the original book Flint spoke before dying: his last words were for his sailor Darby McGraw to bring him some rum.
- "When the king brands us pirates, he doesn't mean to make us adversaries. He doesn't mean to make us criminals. He means to make us monsters."
- ―Flint, I.
- "Friends, brothers... the prize that you and I have been pursuing... is L'Urca de Lima. The Hulk. A prize of almost unimaginable value. Now with this page securely in our possession, we can begin our hunt. And we will succeed no matter the cost. No matter the struggle. I will see that prize is yours. I'm not just gonna make you rich. I'm not just gonna make you strong. I'm gonna make you the princes of the New World! "
- ―Flint to his crew, I.
- "Whoever arrives on our shores first, be it England or Spain, will be in for a most unwelcome surprise."
- ―Flint, II.
- "No matter how many lies we tell ourselves, no matter how many stories we convince ourselves we’re a part of, we’re all just thieves awaiting a noose."
- ―Flint, III.
- "They took everything from us. Then they call me a monster? The moment I sign that pardon, the moment that I ask for one, I proclaim the world that they were right. This ends when I grant them my forgiveness, not the other way around."
- ―Flint to Barlow, VII.
- "There's simply no way of stealing that gold. But there might be something else you can steal. The f**king warship."
- ―Flint to crew, IX.
- "I say to offer to pardon something one fears is the act of a coward. To offer them in volume suggests that their fear of us is becoming unmanageable, that we have shown them what we are capable of and it terrifies them."
- ―Flint to his crew, XIX.
- "Her word will be the last word for this place."
- ―Flint to Peter Ashe XVIII.
- "What does a colonial power do when the men whose toil powers it lay down their shovels, take up swords, and say, 'No more'? Bring down Nassau, maybe you bring it all down."
- ―Flint has some lofty unreachable ambitions... again, XXIII.
- "England has shown herself to me. Gnarled and grey. And spiteful of anyone who would find happiness under her rule. I'm through seeking anything from England. Except her departure from my island."
- ―Flint to Woodes Rogers, XXV.
- "To whatever extent you may be concerned that some day we will clash – worried that though today we be friends, some day you would have no choice but to be my end – I wouldn’t worry too much."
- ―Flint is not afraid of John Silver, no matter how Long he is, XXVIII.
- "The Empire survives in part because we believe its survival to be inevitable. It isn’t. And they know that. That’s why they’re so terrified of you and I. If we are able to take Nassau, if we are able to expose the illusion that England is not inevitable. If we are able to incite a revolt that spreads across the New World... then yeah, I imagine people are going to notice."
- ―Flint, XXXI.
- "You must know this. You're too smart not to know this. They paint the world full of shadows and then tell their children to stay close to the light. Their light. Their reasons, their judgments. Because in the darkness, there be dragons. But it isn't true. We can prove that it isn't true. In the dark, there is discovery, there is possibility, there is freedom."
- ―Flint to Silver, XXXVIII.
- "We will have been for nothing. Defined by their histories distorted to fit into their narrative until all that is left of us are the monsters in the stories they tell their children."
- ―Flint to Silver, XXXVIII.