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James McGraw
Flint 648x1080
Vital statistics
Alias James Flint
Title Royal Navy Lieutenant (formerly)
Pirate Captain
Gender Male
Status Alive
Ships Walrus
Spanish Man O' War
Relationships Hal Gates (Quartermaster, deceased)
Billy Bones (First Mate)
John Silver (Quartermaster)
Miranda Barlow (Lover, deceased)
Thomas Hamilton (Lover, deceased)
Hennessey (Superior Officer)
Appearances First: I.
Portrayed by Toby Stephens
Gallery James Flint Gallery
"Flint’s made you more money than any captain here."
"But lately he hasn't."
"Well, that will change.
"
Gates and Mr. Scott[src]

James McGraw, better known as James Flint, is a pirate captain in the Caribbean, known throughout the West Indies as being the most feared of all the Golden Age pirates. Originally an officer of the Royal Navy, he eventually became one of the most successful pirate captains in the Bahamas. His charisma masks a deep, simmering rage, and a propensity towards breathtaking violence. In order to hold off the British and Spanish forces he’ll 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.

Biography

Background

Royal Navy

Lieutenant Flint

Lieutenant James McGraw of the Royal Navy.

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.

Flint Maria Aleyne

Flint after killing the passengers of the Maria Aleyne.

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 lover Thomas and for his and Miranda's own exile.

Season 1

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.

Flintblood

Flint, victorious in his duel against Singleton.

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.

Bonesflintwalrus

Flint and Bones struggle to free the Walrus.

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.

Gates Death S1E8

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.

Season 2

Ep9-1

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 the Spanish. 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 hey 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 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 to do something about Vane, but he worries she cannot be trusted.

Ep13-5

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 they will attack the fortress with his ship. 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. While 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 the walls of the fortress. 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. Unbeknown 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 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.

Ep16-4

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.

Ep18-10

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 row boat. As Colonel Rhett and his men prepare to fire at the rowboat, 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.

Season 3

In the months since the end of Season 2, 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 realise 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, DeGroot 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.

303show 2560x1440

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.

Village

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” Maroons King, Mr. Scott, have arrived 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.

XXIV 3

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.

Black sails toby stephens

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 boogieman for the governing powers to fear; not Flint, but king Long John Silver.

Personality

Flint is known throughout the West Indies as being the most feared of all the Nassau pirates. Arguably, one of the strongest fighters in the series, with sword, fists or pistol; he was defeated in a duel with Blackbeard only after weeks of starvation. He uses fear to lead others, and is fearless himself. In addition, he is the pirates best navel strategist, which even Vane acknowledges.

Flint is very charismatic, a cunning manipulator, shrewd and ruthless. Part of what distances him from his own crew is his classical education, and he can be mistrustful of them. He believes himself to be 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 towards 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, then he keeps it check briefly until Miranda’s death. Afterwards he snaps, having a massive freak out, until Silver gets him in check again.

Trivia

  • Flint is a fictitious character created originally by Robert Louis Stevenson.
  • In Treasure Island, he died only a few years before the start of the book, so given the series is set twenty years beforehand, don’t expect him to die anything soon.
  • His first name is revealed as James in Miranda Barlow's letter to the authorities in Massachusetts.[1]

Memorable Quotes

"Whoever arrives on our shores first, will be in for a most unwelcome surprise."
―Flint[src]
" Her word will be the last word for this place."
―Flint
"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 after confronting Singleton[src]

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[2]

" 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[src]

Appearances

References

  1. VI.
  2. XXV.
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