Full credit goes to @bittersuites for the idea, who suggested that James Flint and James Norrington should at some point meet in the same Tortuga bar and get drunk together:

He’s been drinking for the better part of an hour before he realizes he has company.

It’s late – not that he cares. It’s odd, but the lack of purpose that accompanied the loss of his commission has blurred time, somehow, or maybe that’s the drink, turning minutes into hours and vice versa. It’s a welcome blur, on nights like this particularly, when some sadistic part of his mind won’t stop turning over old hurts. The hour doesn’t seem to matter to the barkeep, either, though the deafening roar of the tavern is starting to die down as more pirates reel their way out, headed to their berths or to their lovers or to the alley to get sick.

“You know you have an audience, right?” He turns to find a red-haired man sitting beside him, drink held lazily in one hand, a bottle in the other. It’s the fact that he’s not drinking straight from the bottle that gets Norrington’s attention – most wouldn’t bother, especially here. He raises an eyebrow, and the other man slides the bottle toward him. “Two of them. If I had to guess, I’d say they think you’re an easy mark.”

Norrington snorts.

“They’re welcome to try it. Why bother telling me?” The other man gestures to his worn naval uniform jacket.

“I’ve been where you are now. Thought I’d spare you the mugging.”

Norrington turns fully now to face the other man.

“Unless you’ve been run out of the Navy for doing something profoundly stupid and found yourself in this shit hole drinking rat piss and wondering where you went wrong with your life, then I sincerely doubt -” The other man did not speak. He simply gives Norrington a look – a bitter, half-amused expression that turns up one corner of his mouth, and Norrington stops.

“What rank?” Norrington asks, curiosity fired now.

The red-head takes a drink.

“Leftenant.”

Norrington wracks his brain. The rank and file defect often enough, but an officer? There would have been talk, and the only such case he can recall that wasn’t later hanged is – He looks the man up and down.

“James McGraw?” Surprise flashes through the other man’s green eyes, and his mouth twists.

“And you would be -?”

“James Norrington.”

McGraw snorts.  

“James would seem to be a popular name for washouts.”  

“You’re a bit more than a washout – you went native.” Norrington points out. “Nassau. You were there, weren’t you?” McGraw doesn’t answer, just stares out at the room, and Norrington presses the point. “Tell me – do you prefer McGraw or Flint?” The other man’s face spasms, and he takes another drink.

“Flint.” It’s a lie. He can hear it in McGraw’s voice, sees the pain that flashes across his face as he says it, and he watches him for a moment, frowning thoughtfully.  He’s not a Commodore now. Flint is the Navy’s problem, not his, and the man did attempt to help him, whether out of genuine sympathy or not. In fact, Norrington finds himself studying the other man with a sort of morbid fascination. He’s not what he had expected, somehow, and yet everything he expected at the same time. He certainly looks the part of the pirate – hair pulled back in a tail, one ear pierced, wearing a worn coat and a sword belt that looks as if it has seen hard use. It’s difficult to tell sitting down, but he thinks Flint might be shorter than he, and it surprises him. The tactical genius that made experienced captains quake in their boots and lesser men piss themselves should be taller, he thinks, and yet there is something about Flint’s eyes and bearing that make him imposing, give him all the gravitas that had united the pirates of Nassau into a formidable resistance.

“Trying it would be a bad idea,” Flint points out deceptively mildly, and Norrington starts.

“Beg pardon?”

“You’ve been staring for the last three minutes. You had a reputation as a pirate hunter. Don’t try it,” the other man elaborates, and Norrington snorts.

“I’m alone, on an island full of pirates, sans commission, and halfway through a bottle of rot gut. What part of that makes you think that I would attempt to arrest you?”

“Tripoli.” The name drives the air from Norrington’s lungs, and for a moment, he can hear his men’s shouts again, the howling of the gale, Andrew’s cold, accusatory eyes at the court martial. He swallows, eyes closed, trying not to be ill. When he opens them again, Flint is still sitting across from him, and the other man seems to realize that he’s crossed a line, because he pushes the bottle wordlessly in Norrington’s direction.

“Don’t mention Tripoli,” he grinds out, and Flint nods.

“Not just a pirate hunt, then.” Norrington shakes his head.  

“The beginning of three years of hell,” he spits.

“Word out of Jamaica was – sparse, at the time,” Flint says carefully. “Something about Jack Sparrow and the Black Pearl?”

“You wouldn’t even begin to believe it if I told you,” Norrington says, and Flint looks at him skeptically.

“I’ve been a sailor for thirty years. Try me.”

“You’d see me locked in the madhouse for even mentioning it.” Flint’s face spasms, and for just a second, there’s a flash of real pain on his face.

“No,” he says finally, roughly, and oddly enough, Norrington believes him. He cradles his glass between his hands for a moment, staring into the bottom of it through the nut-brown rum. What does it matter, really, if he tells Flint or not?  

“Undead pirates,” he says, and Flint gives him an odd look.

“Undead… pirates,” he repeats slowly. He looks suspiciously at the bottle by Norrington’s elbow. “What the fuck have you been drinking?”

“I told you you wouldn’t believe it,” Norrington says, and Flint snorts.

“You’re right – I don’t,” he says. “Any more than those fucking ridiculous tales of Davy Jones come to life and stalking the West Indies in person.”

Norrington snorts.

“Better a tall tale about squid-people and eldritch abominations than a second pirate uprising, at least as far as the Empire is concerned.”

“If they admit to it, they might have to admit no one wants them here,” Flint said darkly, and Norrington grunted agreement.

“Undead pirates,” Flint repeats, tone still skeptical, and Norrington takes a drink and doesn’t explain any further.  

“Speaking of tall tales,” Norrington pipes up after a moment, “Weren’t you supposed to be dead?” The corner of Flint’s mouth turns up, and he raises one eyebrow.

“You’ve got plenty of room to talk,” he says dryly, and Norrington acknowledges the jab with a wry twist of the lips.

“Must be the name.” The rejoinder brings a brief smile to Flint’s lips.  

“It’s certainly not the upbringing,” Flint answers. “You’re Admiral Norrington’s boy, aren’t you?”

Norrington doesn’t answer, just gestures to the innkeep for another bottle.

“You were Admiral Hennessy’s man, I believe.” Flint nods, and Norrington turns back to his drink, refilling his glass from the new bottle. “He’s dead,” he says. A strange mix of emotions flashes across the pirate’s face, ending in a sort of shuttered look, whatever he’s feeling locked away behind a stoic mask.

“How?”

“A wasting illness, from what I understand.” Flint flinches, and pours himself another drink, which he downs in one quick gulp.

“We never did get the full story, you know.”

Flint frowns, and Norrington gestures expressively with the bottle. “About what happened. One minute you were the Admiral’s favorite – the liaison to Lord Hamilton’s son – and the next -”

Flint looks vaguely surprised.

“You can’t have been more than a midshipman, if that. How the fuck did you even hear about it?”

“I remember my father shouting at Hennessy about it. Claimed the man was licking Lord Hamilton’s boots and shamelessly allowing him to use the Navy to his own ends.”

Flint stares at him incredulously.

“You’re telling me that Lawrence Norrington took my side.”

“Ironically, yes.”

“Lawrence ‘you’re nothing but a Johnny jump-up from the ranks don’t get any ideas’ Norrington?”

“The bastard’s my father, I think I’d know the sound of his voice when he’s having an argument with someone.”

Flint blinks, and then, unexpectedly, starts to chuckle.

“Something funny?”

“He hated everything to do with me – with Thomas’s proposal, and yet – And that bastard Hennessy wouldn’t -” The laughter is shading into the hysterical now, and Norrington eyes his drinking companion with concern. Flint waves him off, getting himself back under control, and shakes his head, pouring himself another glass.

“Hennessy did have something to do with your disgrace, then.”

Flint snorts again.

“He allowed it – took Alfred Hamilton’s word over my own and drummed me out of the Navy without so much as a chance to defend myself, not even to him.”

“On what charge?”

“Officially? None.”

Norrington rolls his eyes.

“Sodomy, or gross dereliction of duty?”

Flint glares, and Norrington gifts him with a singularly unimpressed look.

“Please. You’d hardly be the first, or the last, for either.” He gestures to his own ragged form, and Flint’s glare softens a little before he turns away, back to his glass.

“It doesn’t matter which,” he says finally. “Your father was right, for once. The charges were an excuse – one they used to see me exiled and Thomas imprisoned in Bethlem.” Norrington winces. He’s heard the rumors about the Earl’s eldest son, and not the polite ones that said he’d committed suicide from grief for his wife and her lover. He casts about for something to say, and ends up simply pushing the bottle toward the other man, a return of Flint’s earlier gesture, and the pirate takes it with something approaching gratitude. They sit quietly for several seconds, and then Norrington takes hold of the bottle, splits the remaining rum between their two cups, and raises his.

“To the British Navy – may it stop recruiting green-eyed fools named James.”

“To the Navy,” Flint echoes. “May it burn in hell, along with the rest of the Empire.” They knock back their drinks, and Flint looks around.

“Your audience has fucked off,” he notes, and Norrington turns, somewhat surprised, only just remembering why the other man sat down at his table at all.

“They must have cleared out at the word ‘squid-people.’”

Flint snorts, and then looks at Norrington speculatively.

“You never answered the question,” he says slowly. “What did happen with the undead pirates?” He makes a face, as if he can’t quite believe the words ‘undead pirates’ just passed his lips.

Norrington raises one eyebrow, half his mouth raised in something approaching a smile.

“I’m going to need a lot more rum to answer that question,” he says, and gestures to the barkeep again.

Several hours later:

The tavern has gone utterly quiet when the door opens again and two figures converge on the drunken pirates, one blonde, one dark-haired. They stop at the sight of one another, and then the blonde steps into the light and Long John Silver and Elizabeth Turner eye one another warily.

“Lady Turner.”

“Mr. Silver.”

He nods to the two passed out in a corner, Flint’s head resting comfortably against Norrington’s shoulder and Norrington’s arm propped on Flint’s shoulder with his head thrown back, snoring softly.

“I’ll collect mine if you’ll collect yours and we won’t speak of territory. Agreed?”

“Done.”