Title: Gentlemen of Fortune

Chapter 1: Early in the Morning

Rating: PG-13

Disclaimer: Pirates isn't mine, which I'm sure comes as a big surprise to many of you. Alas, it belongs to Disney.

Summary: An innocuous request leads to a look at Captain Jack Sparrow's past, complete with encounters with the East India Trading Company, slave traders, corrupt officials, treasure, trips to Singapore, and the truth behind the kohl and hat.

Warnings: Gen/het/slash

A/N: People really ought not to encourage me to write *sticks out tongue at Fyre:P* Chapters will be written whenever I feel like it since I shouldn't be starting another story at this point anyway. Will it ever be finished? The answer to that is in this quote, "How the hell should I know?" I did a lot of historical research for this, but since the movie isn't exactly historical I've had to fit the facts to the fiction occasionally and damn the consequences. Special thanks to my beta readers Ashfae and Siria Black.


            Contrary to popular belief, Jack Sparrow did not get drunk that often. Oh, he drank – he wouldn't be considered a man or a pirate if he didn't – but he reserved getting well and truly drunk for those times when he was thoroughly depressed or thoroughly happy. It was the former that had led him to get drunk this evening, breaking into a barrel of rum that they had stolen and generously sharing it with the crew. They had put into a small, uncharted island, started a fire and started drinking. 'Twas a pity that everyone's spirits had improved except his, and he was staring blearily into the fire wondering why this was the case when his crew interrupted him.

            "It's your turn, Captain."

            Jack looked up and tried to focus on faces that were blurred beyond recognition. "Wha?"

            The still slightly fuzzy form of Gibbs hunkered down in front of him. "We're telling stories, sir. Whoever tells the best wins the last bottle of rum."

            Only one part of Gibbs' sentence made its way through Jack's head. "The rum's gone?"

            Gibbs' shook his head. "No. Not yet anyway. But it will be soon, and it's your turn to tell a tale. Something we haven't heard now, mind."

            Jack considered. The thought of backing out of the contest or just declaring the last rum to be his never crossed his drink-addled brain, but there was one problem. Captain Jack Sparrow never shied away from talking about himself, and any story he was wont to tell had probably been heard by the crew at least once, if not fifty times – he really loved that sea turtle one.

            "Er, have I told ye about the time I stole John Gladman's ship all by me onesies?"

            "Yes," came the drunken chorus.

            "The mystery of Little Red Rock?"

            "It wasn't so little!" yelled the crew.

            "The time I had three Chinese whores as a reward for saving a Chinese merchant's opium trade?"

            The crackle of the fire was suddenly extremely loud. "No?" ventured one of the crewmen.

            "Eh, well, I don't remember that one either." Jack shook his head. "Too much opium." A few of the crew made disappointed noises.

            "How did you become a pirate?" called the strong voice of Anamaria from the back of the group. She had a tendency to get even more violent when drunk (though it may have had something to do with all the offers the men tended to give her while in the same state) and there was a large space around the tree branch where she sat.

            "Wha?" said Jack with some alarm. He preferred the rumor that he had sprung full grown and ready to raid out of the wheel on the Black Pearl's deck.

            "That's a good idea," called out Marty, otherwise known as the shortest pirate in the Caribbean.

           "Something from your early years," agreed Gibbs. The rest of the crew called out their drunken approval of the topic.

            Jack gritted his teeth and took a long swallow of his rapidly emptying bottle of rum. The reason he didn't talk about his early years was because he had been, in his own opinion, unaccountably stupid back then. Of course, everyone was stupid when they were young, and he hadn't been as stupid as some. And it certainly hadn't stopped him from having adventures. His luck had sometimes been quite poor, but that didn't matter. Another sip of rum and a slow smile began to creep across his face. It wasn't as if he had to tell the truth after all…

            He drained the bottle and began to speak.


            "Read the paragraph again, love," called Mrs. Hatter in singsong voice from across the room.

            Jack gave his mother a plaintive stare that was completely ignored, then turned his attention back to the text. "Why hello, Mr. Spoon. I always enjoy taking a walk around the promenade with such a beguiling fellow as yourself. You must tell me who does your polish." Jack paused.

            "Polish, Mum?" he asked, but she wasn't listening. Instead she was waltzing around the room with a dry mop, humming Greensleeves – off key. "Can I read something else, Mum?" She bowed to the mop and began another song. Jack took that as a yes.

            With undisguised glee he pulled a battered pamphlet out of his pocket. He'd had to fight Rodney Corner for it and ended up with a bruise that covered half his chest and made breathing slightly painful, but it was worth it. He, Jack Hatter, had a copy of the best and most famous pirate pamphlet that had circulated London in the past years.

"The Doings of the Infamous Grand Pirate, Captain John Avery," he read out loud for the benefit of his dancing mother. He continued to read softly to himself of the pirate's greatest escapades and of how he had never been caught but was living like a king in Madagascar with five wives. It made for much more exciting stuff than the strange nonsensical tales his mother wrote for his continued education.

As the only son of a prominent and prosperous hatter, he'd had proper schooling when he was younger, but when Grandfather died the business took a down turn. His schooling was now seen to by his mum – on her more lucid days. On the days when she claimed to be the queen or a teacup Jack was free to do what he wanted. And since today she looked like she was well on her way to declaring herself Anne Boleyn, he stowed his chalk, board and various papers in a nearby chest, and placed the pamphlet carefully back in his pocket before slipping out the door.


            The infamous highwayman, Jack Hatter, made his way stealthily towards his next prey. Granted, the stall piled high with savory pasties was not quite as exciting as a coach filled with royal duchesses and jewels, but he had little time to be picky when his stomach was calling out for sustenance. Doing his best to blend in with the wall he was pressed up against, he edged his way towards the cart, praying that the blonde Mrs. Hartnet would remain occupied with her customers so he could get away with his prize. He fancied a pork pie today, and it just so happened that the steaming pork filled pastries were closest to where he was standing. Plastering a casual expression on his face, he reached out for a pasty. He was almost there when Mrs. Hartnet began to turn towards him. Quickly, he pushed his tell tale hand into the pocket of his coat.

            A knowing look came into Mrs. Hartnet eyes as she caught sight of him. "Jack Hatter. Got any money for me today?"

            Part of Jack began to panic; the other part of him gave Mrs. Hartnet a winning smile and shook his head.

            She sighed, and casually wiped off her grease covered hands onto a cloth kept just for that purpose. "Explain to me why I should be feeding you then."

            "Well," began Jack, thinking furiously. "People are always in need of feedin', especially here in London, but there's an awful lot of people here and not all of them pass by your stall, so even if you did want to sell your pasties to all of London you couldn't. Therefore," he held up one hand to make his point, "you'll always have pasties left over at the end of the day and they like to spoil if you leave them too long. So, providing me with one now will not hurt your business and will make me happy." He gave her a big grin.

            Mrs. Hartnet's eyes had glazed over. She shook her head to clear it. "You want to repeat that?"

            Jack couldn't actually remember what he'd said, so he shook his head no and gave her a pitiful look.

            She sighed, then reached out to take a pork pasty from the pile. "If I didn't know about your mum, and that bastard father of yours…" she muttered.

            "What was that?" Jack asked, though he had heard perfectly well. He knew his father was a bastard, and a drunken bastard at that. And anyone who had ever chatted with his mum for a little while knew she was mad.

            "Nothing." She handed him the pasty. "Now off with you. Go rob someone else!"


            It was dark out, and the fog was beginning to obscure the few lamps on their street when Jack made his way home. The day had gone well, especially when he and his mates, pretending to be brave English soldiers, had surprised another group of boys at a well, leading to a fast and furious water fight. He wasn't quite sure how he was going to explain to his mum how his trousers had gotten one leg ripped off, but with luck she would believe his story about fighting a troop of thieving Moors and he wouldn't have to think of something more plausible.

            He slipped into the house. The pork pie had made a good dinner, but he was a growing boy and it might be worthwhile to stop off in the kitchen for a piece of bread before he crept upstairs. Long practice had taught him to walk silently, but he was so preoccupied with thoughts of the fight that day that he didn't notice the soft glow of a turned down lamp flickering through the crack under the kitchen door.

            Consequently, when he pushed open the door to find his father slumped on the kitchen bench, staring dully at the lamp on the table, he jumped and nearly ran back into the darker and safer part of the house. A moment of standing there silently revealed that Jack's father was in a drunken stupor and not likely to move. But still Jack stood there.

            Enough people had told Jack that he looked like his father that he supposed it was true. They both had dark hair and eyes, but where Jack was slender like his mother and relatively short for his age, his father was a big man towering over six feet. The height didn't show from where he was slumped, but the nose broken in a fight long ago and the slight paunch did.

            Jack had the feeling that like some strange wild beast, if he took his eyes off his father for a moment, the man would attack. But Jack was no coward and he wasn't afraid of his father. He really wasn't. To prove it to himself, he took his eyes off the man and walked carefully towards the shelf where the bread was stored.

            The blow came only after he had taken the food, a savage clout to the side of his head that set his ears ringing and caused him to drop his piece of bread.

            "You abandon your apprenticeship, hiding behind that bitch's skirts," said his father angrily, his words made more deliberate by the drink.

            Jack clenched his fists together at the insult to his mother, but a sense of self preservation kept him from lashing out. His father would not hit him as long as he could talk to Jack instead.

            "And now I catch you thieving?!"

            "The food's as much mine as yours," retorted Jack, ignoring the fact that he did spend part of his days in petty thievery. What else was he supposed to do when his father spent their money on drinking and gambling?

            His father leant down towards him, giving him a good whiff of his ale soured breath. "I work for that food, lad. You play."

            "At least I don't play at spending all our money."

            The second clout to the head drove home that it had been a stupid thing to say. Jack prepared himself for a beating, but a tell-tale creak gave him new hope. He looked to the kitchen doorway and sure enough, his mother stood there, dressed for bed. Her eyes didn't seem to see them, but that was okay. Father would usually behave so long as she was there.

            When grandfather had died, Jack had only been eight. He had been happy then to be apprenticed to his father and grandfather, the two greatest hat makers in London. But in truth, his father hadn't made many hats. In truth, his father had been lucky to marry above his station to a beautiful woman and to inherit the business, though even now his mother still owned some of it. Her father had been kind.

           Father didn't think he was lucky though. He called grandfather stingy and a bastard, especially when he was drinking, something that happened more and more often as time passed. He took out his frustrations on others – strangers at the pub, and then Jack's mother. There had been a year where she cried every evening in her room, where she struggled to hide the bruises and to keep the house running. It was Jack's mum who taught him how to imagine things, to play in the stories that they and others made up. And as the days passed she began to imagine things even more, until everything was imagination and everything was real. Jack remembered the night she came down wearing nothing but each of her bruises, circled in black rings made of kohl as though she had some strange disease. She had giggled softly to herself and asked his father to dance, calling him "my lord", but all the while staring at the corner with blank eyes. Not even a slap from his father stopped her laughter.

His father disappeared for three weeks after that, and when he came back he never touched his wife again, though his son was a different matter. Even less hats were made, and Jack didn't want to visit the shop anymore.

            "Mum!" he called in relief at the sight of her standing in the kitchen doorway.

His father turned to look. "Dammit, Mary! Get back to bed."

            "I've come to go a-shopping," responding his mother in a singsong voice. She reached down and picked up a basket from the floor which was indeed used for shopping.

            "Not in the bloody dark you won't!"

            "Where shall I go, then? To heaven or hell? Or maybe purgatory. Am I Catholic?"

            His father shook his head slowly. "You're mad, that's what you are, and I curse the day I was ever saddled with you." His voice was hoarse, but the anger from before had drained out of him.

            Jack picked up the bread and hid it in his sleeve before running to join his mum. "We'll go to heaven together, Mum. It's up the stairs." He began to pull her out of the room.

            She patted him on the head. "Such a good boy."

            His father couldn't resist the last word though. "Thieves go to hell, lad," he called after them before Jack could pull the kitchen door shut.

            "So do bastards, Father," Jack muttered as he led his mum upstairs.


            A fortnight later, Jack was up early to help his mother in the kitchen. The quicker they got done with the morning chores and his lessons, the quicker he could be outside. He swept the floor with all the enthusiasm and carelessness of a teenage boy while his mother cooked some simple porridge for their breakfast. Both of them ignored Jack's father when he wandered into the room.

            Jack swept one of the corners of the room twice before his mum served the porridge. Father liked quiet in the mornings, and they were happy to oblige since it got him out of the house faster. There was an odd gleam to father's eyes this morning, but Jack ignored it in favor of food. He was surprised when his father pushed the porridge away and stood up.

            "Get your things, lad."

            "Hmm?" Jack swallowed his mouthful of porridge. "What for?"

            "I have to do some business in Greenwich this evening. We'll be spending the night at the tavern there."

            Jack glanced at his mum who was drawing slow circles in her porridge. "I don't want to go."

            A flash of anger crossed his father's face as well as another emotion Jack couldn't place. "I don't care if you don't want to go, you idiot. I'll be handling a lot of money tonight and I need someone in the room to make sure it isn't stolen. Surely you can do this one thing for your family?"

            Jack felt chagrinned. Chances are most of the money would end up being used for alcohol or gambling, but some of it would get to his mum and himself. And if he was there tonight, he could make sure that even more of it made it into their pockets than his father thought. "I'll come."

            He ran upstairs, grabbing a small sack and stuffing whatever clothing was handy inside. A water flask followed along with some cached food, since his father was sure to forget Jack was up in the room once he was deep in his cups. Last went Jack's treasured pamphlet on Captain John Avery. He wouldn't need to take his lessons with him since he wouldn't be gone long, and he rejoiced at the day of freedom.

            Downstairs, his mum seemed to be under the impression that he was going on a quest somewhere. "Fair knight, you will need these on your quest, and you have my heart as well," she intoned, holding out a small bottle of cloves and a few sticks of kohl with all the solemnity of a priest with the sacrament.

Jack took them, reminding himself to return them tomorrow, since she would need the cloves for cooking. "Thanks, Mum." His father was waiting impatiently off to the side, a small bag of his own at his feet.

            His mother smiled, looking for all the world like a real lady seeing her knight off, despite the threadbare dress she wore and her hair in disarray. "I would give you a token of my love to bear into battle, but I'm afraid I have nothing but this kiss." She was giving him a quick kiss on the lips before Jack could pull away, sputtering in indignation at being treated like a little boy.


            "Is aught wrong, fair knight?" His mum looked puzzled. Jack looked away and shook his head. He did what he usually did then, and played along.

            "Nothing is wrong, fair lady," he said, giving her hand a quick kiss before heading for the door, his father in front of him. "We'll be back tomorrow, Mum!" he called before they left.

            "Don't burn down the house!" was his father's last call to his wife.

            Jack scowled at him. "She's not going to burn it down."

            His father looked preoccupied when he answered. "There's a first time for everything." He set off through the crowds, and Jack was forced to follow him.


            The walk to Greenwich took longer than either of them expected, since they had to thread their way through the morning traffic. Carts loaded with goods crowded the narrow streets on their way to the market, and making one's way on foot was foolhardy if not downright dangerous.

A little before midday they reached the crowded docks of Greenwich. It had been a long time since Jack had been here, and he stared in open fascination at the bustle of the great ships at dock with their sailors scrambling over their rigging, or transporting goods to and fro.

            His father stopped in a nearby tavern and paid for lodging for the night. Then settling Jack in with a bowl of soup and some bread, he set off on his business. Jack had been told to wait, but he resolved to go exploring as soon as he finished his meal.

            Outside, he watched the sailors with fascination until they got annoyed with him and shouted at him to go away. When Jack finally worked up the courage to ask a bearded sailor what he was doing with the large pile of ropes that he was tying and untying, he found out the man only spoke in a guttural tongue that Jack decided was German. Disappointed, he wandered the dock, asking questions and occasionally getting answers, but more often getting curses. Jack made a point of memorizing a few of the worst ones to impress his friends with when he got home.

            As the afternoon progressed, the sailors drifted away to spend their hard-earned wages in the taverns, or to visit their homes if they were lucky. Jack cornered a returning fisherman to discuss the days catch, but after his eyes glazed over for the third time at the fisherman's complicated explanation of currents and fishing techniques he decided to find the tavern again. It took awhile since Jack had forgotten its name, but eventually he popped his head into the right one and spotted his father in deep conversation with a tall, brown haired man.

            He approached them cautiously, noting the drink on the table and wondering if his father would be angry at him for running off. He was surprised when his father smiled at him instead.

            "There you are, lad. Was beginning to worry." He addressed the brown-haired man. "This is my boy, Jack, thirteen years old and fit. He can even do letters, not that that's very useful."

            The other man smiled at his father, then turned to look him over. The way his smile grew wider sent a thrill of warning through Jack. "I'm sure he's very useful." The man's voice was deep, with a northern accent. He drained his cup. "Come, my friend, let's finish our business."

            Jack's father nodded, finishing his own cup before following the other man up the stairs. As an afterthought, he gestured for Jack to follow. The small room they entered was crowded with the three of them inside.

            "Shut the door, Jack."

He did, and so his back was to them when something large and heavy crashed down on his head. His sight immediately went black, but he could hear for a few moments longer.

            "Are you satisfied with him, Charter?" his father asked nervously.

            "Oh, yes. I'm quite taken with the lad."


            "Don't worry, Henry. Your debts will be paid. In fact…"

            Jack wanted to hear more, but the blackness was overwhelming and soon he was left alone to sink into oblivion.


            The ground was moving strangely when Jack woke up. Opening his eyes revealed only dim shapes. A warehouse or something, he guessed. He tried to get up, but discovered his hands were tied together and looped around a large wooden beam. A large wooden beam that was swaying gently from side to side. He wasn't on a boat, was he?

            Straining his ears and wishing his breathing weren't so loud, he was just able to make out the gentle lap of water and the more harsh cries of men shouting orders above him. He listened for a long time, each moment confirming his second guess. He was on a boat.

The sound of the nearby hatch opening was startlingly loud. The brown-haired man, Charter, came easily down the ladder. Jack was surveyed with that disturbing grin again.

"Hello, lad. Glad to see you awake. Welcome on board the Thrush."


Historical Notes: Captain John Avery was probably one of the most famous pirates in Britain in the late 1600s being a contemporary of Captain Kidd. The pamphlet Jack has is actually a reprint since I've set this tale in the 1720s. John Avery actually ended up dying a pauper in Devonshire, but that's a completely different story…

Reviews welcomed:)