By Char
Twitter: @gaypiracy (for Black Sails) & @CharCubed (main), with artwork by @liviladoodles.
Thank you to the team behind Toby Stephens News for giving me the opportunity to put this list together! :) James Flint is one of my favorite characters of all time, and the Black Sails fandom has some of the most incredible fic I’ve ever read in any fandom, so this was truly a pleasure.
This Flint-centric list is ordered by word count and contains fics that are pre-canon, post-canon, and “missing scenes” from within the canon timeline. When compiling this, I did my best to choose ones that I feel bounced off of canon extremely well, with accurate and interesting characterizations for all characters involved. This list includes various romantic ships, but just as many platonic relationships too, and hopefully the end result gives a well-rounded look at Flint's complex interactions with multiple people throughout his life. Platonic stories (indicated using “&” rather than “ / ”) include spotlights on Anne Bonny, Eleanor Guthrie, Jack Rackham, Abigail Ashe, and Madi.
I also tried to tip towards "underrated" fics, so hopefully even those who have been in the fandom for years can find something new to them!
Happy reading!
"We were happy" by liviladoodles
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by urca
In Philadelphia, Anne thinks about a conversation she had with Flint in Nassau.
Relationships: James Flint & Anne Bonny
Words: 1,231 | Rating: T | Chapters: 1
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your hair was long when we first met
by straddling_the_atmosphere
In which Flint shaves his head and thinks of Miranda, and thinks of Silver.
Set between s2 and s3.
Relationships: James Flint/Miranda Hamilton, James Flint/John Silver (pre-slash)
Words: 1,176 | Rating: G | Chapters: 1
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by youatemytailor
"Come on," Silver prompts, craning his neck to catch Flint in his periphery. "Don't tell me Captain Flint is flinching at the sight of a little blood—I've seen you dig a bullet out of your shoulder with your fucking fingers for Christ’s sake, Flint, you can’t be serious—"
"It's not the—when did you get that?"
Strands of hair fall out of Silver’s grip and back over his ear as he struggles in his chair to catch Flint’s eye. "When did I get what? What are you—"
There, behind the curve of cartilage and almost invisible under the red smears, is a small tattoo.
Silver (attempts to) get a piercing. Silver also has a tattoo. James reacts, in a way where there are declarations of love without the words themselves and more mutual understanding.
Relationships: James Flint/John Silver (pre-slash ish?), John Silver/Madi
Words: 3,220 | Rating: T | Chapters: 1
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by mapped
Post-canon. Thomas tries to make James understand that he loves all of him, and yes, that includes Flint.
Relationships: James Flint/Thomas Hamilton
Words: 3,313 | Rating: M | Chapters: 1
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the misplaced half of our lives
by mapped
Madi starts to understand why Silver trusts Flint.
Relationships: James Flint & Madi, John Silver/Madi, James Flint/John Silver, James Flint/John Silver/Madi
Words: 3,401 | Rating: T | Chapters: 1
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For the Caged Bird Sings of Freedom
by craftnarok
Flint finds a sad-looking caged bird aboard a merchant ship and, being a secret soft-hearted sort, he decides to liberate it.
A backstory for the bird cage seen in the back of Flint’s cabin in season one.
Relationships: Gen.
Words: 3,456 | Rating: G | Chapters: 1
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by samedifference61
Flint leans in close so the others won’t hear him. “She wants me to teach her how to use a blade.”
Set before season 4. Flint finds it difficult to refuse Madi, and agrees to teach her to fight. Silver has insecurities about his place in their lives.
Relationships: James Flint & Madi, James Flint & John Silver, John Silver/Madi
Words: 3,835 | Rating: T | Chapters: 1
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Five Times James Flint and Jack Rackham Cross Paths (and one time they don’t
by forbiddenarchives
The first time Captain Flint becomes aware of the existence of Jack Rackham is when he has to split a prize with Charles Vane’s crew, and Vane demands the books.
“The books?” Flint asks, incredulous.
“The books,” Vane repeats, happy to explain the concept. “You know, ink, paper. Dead men’s words that no one cares about.”
Glimpses that span the entirety of the story.
Relationships: James Flint & Jack Rackham
Words: 4,925 | Rating: T | Chapters: 6
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by shirogiku
Series summary: What if Abigail remembered James as Thomas and Miranda's friend?
Part 1: Little Abigail and James share a moment in her father's library.
Part 2: Abigail, Flint and Miranda en route to Charles Town.
Part 3: Abigail never meant to choose sides. (AU where Miranda lives)
(I’m including this mostly based on parts 1 and 2!)
Relationships: James McGraw & Abigail Ashe, James McGraw/Thomas Hamilton, James/Miranda/Thomas
Words: 5,190 | Ratings: G & T | Chapters: 3
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by AstronautSquid
Her sketches of people tended to veer into caricature with their lively emphasis of all things out of the ordinary - a large nose, a double chin, a foppish gesture -, and had thus quickly been ruled unfit for display among polite company.
Thomas encouraged her to keep a rotating selection framed on a dresser in the chamber connecting their rooms.
It was a week into their affair that Miranda first sketched James.
Relationships: James McGraw/Thomas Hamilton/Miranda Hamilton (& their separate relationships within that)
Words: 5,525 | Ratings: M | Chapters: 1
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same bottle, same gun: two shots
by AstronautSquid
Pre-canon. Nassau, 1708. Eleanor Guthrie remembers a moment in the life of Lieutenant McGraw; Captain Flint doesn't.
A look at a friendship being built on mutual respect, and queer solidarity.
Relationships: James Flint & Eleanor Guthrie
Words: 5,824 | Rating: T | Chapters: 1
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sketch by liviladoodles
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by youatemytailor
Flint and Silver have conversations on the ship on the way to Savannah. Tense, realistic, and bittersweet, this seamlessly works as a sequel to canon events, and is an excellent exploration of the characterizations of them both.
Relationships: James Flint/John Silver
Words: 8,648 | Rating: T | Chapters: 2
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by youatemytailor
Silver is in the room when it happens. He’s not sure if he’s glad for it, in retrospect.
Flint gets sick. Silver, drawn into his orbit, takes care of him. Set in mid-s2, during the fort standoff storyline.
Relationships: James Flint/John Silver (pre-slash)
Words: 10,135 | Rating: T | Chapters: 1
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Don’t Fear the Ships (Fear the Black)
by Farasha
“You can't read sea charts."
"Can't is a strong word."
Set in season 3. Flint teaches Silver how to sail. As with everything they do, there's a lot more going on unspoken. Or: Silver tries to convince Flint that it would be a bad thing if he died.
Relationships: James Flint/John Silver
Words: 10,716 | Rating: E | Chapters: 1
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by sebastianL
Post-canon, in the months following the finale, with a focus on Toby / James’ moon tattoo.
James and Thomas relearn each other and restructure their relationship, exploring the complexities of the men they’ve become after what they’ve experienced. While it’s not always difficult, it’s not always easy either.
Relationships: James Flint/Thomas Hamilton
Words: 10,819 | Rating: M | Chapters: 1
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by robotboy
You dream for a lifetime of your one great love. James Flint has always dreamt of the sea.
Set from pre-canon through post-canon, this is a soulmates AU featuring dreams and filled with literary references and motifs. The writing is atmospheric and moving, balancing what characters are drawn to vs. what they choose to do with that through their agency, and the imagery is masterfully woven. I couldn’t resist including this as a rec, because I think its uniqueness is a strength, and it’s still in the spirit of the rest of this list.
Relationships: James Flint/Thomas Hamilton, James/Thomas/Miranda, John Silver/Madi, James Flint/John Silver
Words: 11,805 | Rating: E | Chapters: 23
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The Journal of Lieutenant McGraw
by beatriceHB
Encouraged by his senior officer to begin writing a journal, James McGraw finds himself documenting a dramatic turning point in his life; his first encounter with Lord Thomas Hamilton, and the evolution of their relationship.
Relationships: James McGraw/Thomas Hamilton
Words: 13,241 | Rating: E | Chapters: 1
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by equestrianstatue
“When I first met you, you were so— unformed. And then I spoke and bade you cast aside your shame, and Captain Flint was born into the world.”
How the Hamiltons made Captain Flint.
Exploring the relationships between the three characters and how they intersect, from pre-canon with Miranda and Thomas’ meeting through when Flint is first “created.”
Relationships: James McGraw/Thomas Hamilton/Miranda Hamilton (& their separate relationships within that)
Words: 23,421 | Rating: E | Chapters: 3
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by lapsi
He levels the pistol at John Silver’s head, lips in the start of a snarl.
The John he was acquainted with would have feigned indignation, raised his hands and his eyebrows and used Thomas’s pacifism to defuse the threat. Wheedled his way into a calmer state of affairs. Silver doesn’t flinch, an uncustomary flatness in his countenance as he returns the eye contact.
It falls to James to speak, which he does with as much retaliatory coldness as he can muster. “Get out of my house.”
Post-canon, set about 18 months after the finale. John is drawn to Savannah, desperate for help. James is, in turn, pulled back to the chaos of piracy.
Relationships: James Flint/Thomas Hamilton, John Silver/Madi, James Flint/John Silver, James Flint/Thomas Hamilton/John Silver
Words: 47,799 | Rating: M | Chapters: 15
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by stele3
Post-canon. There is no description for this series as a whole. This is a variation on the known theme of "Silver arrives at James and Thomas' house for a plot-related reason, and their healing/relationships develop slowly from there," but it also features two original female characters that they live with. Also, in this series, Silver is Jewish. Madi is not in it from the start, but she arrives later.
There are no words to adequately describe this story. The way the author expertly uses language(s) in this is unreal, the sheer amount of care and detail put into the historical setting, the way different characters’ POVs are so unique and each done justice... It's phenomenal. I love the complexities, moral quandaries, and layers of wisdom gifted to readers through these words. The characters are so alive and so rich with the diversity of their thinking and cultures, and the way their lives intertwine and grow together so slowly and beautifully is incredible. Much like the show, this series is filled with both light and dark elements and shies away from neither, and gives you just as much to think about.
It’s probably one of my all-time favorite works of literature and a golden standard for accurate characterizations of these characters, and I feel it’s vastly underrated, so I couldn’t not include it on this list.
Relationships: James Flint/Thomas Hamilton, James Flint/John Silver, Madi/John Silver, James Flint/Thomas Hamilton/John Silver
Words: 116,535 | Rating: all/various | Chapters: 11
sketch by liviladoodles
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