Disclaimer: This story is AU, since there is at least 100 years difference between POTC and SH, so I played with the time line a bit.

Jack Sparrow sat at the pub in Tortuga, waiting. He allowed his eyes to roam the place and its bonny lasses. He wondered which of the lucky ones he'd been with would be the one to step forward and slap him silly. He also tried to wager how many of those did he deserve. A pretty brunette caught his eye at the end of the room and he inwardly cringed. 'What was her name...' he thought quickly as she made her way over. Judging from the angry blush that adorned her cheeks he could gather what she wanted with him. 'Something with an M... Marry? No.. Maggie? No...Margaret- Yes!'

"Margaret", Jack greeted her as sweetly as possible, flashing her his best grin. She crossed her arms over her chest and raised her brows, waiting. Jack thought fast. "How lovely it is to see you again- I was just thinking of you!" The disbelieving look on her face and the fact he hasn't been slapped yet encouraged him to continue. "Honestly! I was just sitting bored as a stiff in this joint and thought to myself- 'whatever happened to that delightful Margaret?'" He could see the tense lines in her face relaxing and knew he had her. "It'd be so much better with her around, she was always good for some fun." He nearly bit his tongue as he realized his mistakes moments before the thundering slap met his aggravated cheek. As she walked- no stalked away he muttered under his breath: "So close..."

It was a moment before then, that Will Turner and his wife Elizabeth decided to grace the place with their presence and witnessed the scene, amused. They made their way over to the muttering Jack and stood behind him.

"Well, if every lady here gave me the "warm welcome" she gives you, I know I'd never feel unwanted", Will said grinning, causing Jack to jump to his feet and envelop him in a warm embrace. Will smiled at his old friend fondly before laughing. "Honest to God Jack, is there a woman here who DIDN'T slap you at one point or another?" Jack seemed to ponder this thoughtfully, stroking his mustache.

"Why, I believe there is," he said slowly, sitting back down. His face broke out with a smile as he added: "Miss Swann." The couple smiled before Elizabeth said: "Not for a lack of trying, I assure you." She stepped closer to Jack and quickly hugged him, rendering him in a state of shock. As she stepped back she lifted her left hand and showed him her wedding ring. "And it's Mrs. TURNER now Jack, or have you forgotten?" He bowed in apology and gestured for them to sit down.

"Perhaps," Jack said sourly, "I would have had a harder time forgetting were I invited to that most celebrated occasion." He motioned with his mug for more drinks for his companions who had the good grace to appear embarrassed.

"You know we would have liked nothing more than to have you there," Elizabeth started, wondering how exactly to say it. Luckily for her, Jack caught the drift.

"But your wedding be it in Port Royal, and I'm a wee bit unwanted there." Will frowned, wondering when was the last time he remembered Jack speaking English wrong grammatically. For a Pirate he seemed to have the odd habit of speaking English punctually correct.

"I understand, truly, I do," Jack continued, taking a large jug from his pint. "But I sure do love weddings." He had such a wistful look on his face, like when one remembers an event fondly in retrospect. Instinctively the two drew closer, holding hands under the table affectionately. Jack nearly grinned, thinking that the saying "true love" applies solely on these two if on no one else. Though he remembered another couple that that same thing could be said about. He shook his head and put on his trademark smirk.

"Tell me this is not your honeymoon," he said good naturedly. Will and Elizabeth relaxed, getting more comfortable. Jack took the news in person well. Though in the letter they sent they did tell him they were married, it was not the same as in person. A waitress came with their drinks and Jack looked her over appreciatively. Will shook his head as Elizabeth chuckled, both thinking the same thing: He never learns...

"Where's the Pearl?" Will asked suddenly, noting he didn't see any other crewmembers. "And it's crew?"

"HER crew, for starters," Jack corrected patiently. "As for your question- I gave the men and Anamaria some time off."

"You gave them a vacation?" Elizabeth asked shocked. "Do Pirates even GET vacation time?"

"Well, it all depends, ya see, on the Captain. Now if said Captain is a fair one, who sailed back from a successful looting of a village, he might be inclined to-"

"Acquiesce their request for a vacation?" Elizabeth asked, chuckling. Will frowned at her and she was about to explain when Jack said harshly:

"Where did you hear that saying?"

Elizabeth was in such shock due to his harsh tone of voice, she had to swallow several time before managing a reply.

"Barbosa," she said quickly. "It's simply something he said to me on his- on the Pearl," she nearly stuttered. She never knew Jack to have that angry glare; he was always in a jovial or maybe sullen mood- never truly mad. It was quite frightening.

Jack's glare intensified for a moment, before he relaxed and returned to his playful manner. "Aye, the unjust of the world!" He exclaimed theatrically, grinning beside himself. "That skeleton steals my ship... My line... My name! He named that wretched monkey Jack! With those beady eyes and hairy face... Did it LOOK like a Jack?" He slumped in his seat and drank some more of his rum.

Will was about to ask him something when suddenly they heard a loud crash. All eyes turned to a drunk, barely able to stand erect, being propped up by the barkeeper.

"I think this gentleman has had enough," the bar keeper said with a kind smile, about to escort him out.

"I ain't finished 'ere yet," the man drawled, swaying violently to one side, before straightening himself up.

"Let 'im sober up with the swine, that's where the likes of him belong," one of the waitresses said, shuffling past. The drunk caught her arm and gave her a lust filled stare.

"Betcha I can tell you where you belong." The man said, licking his lips, as she tried to release her arm. "Let me go!" She said, trying to yank her arm free.

Will looked uncertainly at Jack, afraid of causing a scene. He was about to grab for his sword and demand he leave her alone, when Jack rested his hand on his arm and shook his head. Jack inwardly sighed, knowing well that rescuing damsels in distress never seemed to agree with his well-being. He swiftly got up from the table and sauntered over in his famous gait towards the drunk. He purposefully ignored him and went straight to the barkeeper.

"Might I trouble you for some rum?" He asked the man, placing several coins on the counter. Luckily he was in a generous mood tonight. The bar keeper looked at him astonished that he had the nerve to do so, while one of his waitresses was being harassed. He would have done something himself, surely he would, only problem is his back got caught last week and it would do more damage than good. Jack looked at him intently. "A bottle, if you please," he motioned with his head towards the drunk, who was half way up the stairs with the fighting woman.

The bar keeper stared at him stupidly. Why can't anyone understand a hint? Jack sighed, grabbed the first bottle he saw and on his way back to his table he shattered the bottle upside the man's head. The man immediately crumbled and the crowd, though not daring to do it themselves, cheered appreciatively. Jack inspected them with an amused grin and bowed deeply several times, enjoying his ovation, before returning glowing to the table. Will clasped him on the back. "Well done Jack."

"Jack?" The bar keeper asked, suddenly growing an interest in the hero of the hour. "Jack Sparrow?"

"CAPTAIN Jack Sparrow," it was like fighting windmills and more of a habit than actual grievance, but it still annoyed him. The bar keeper motioned to the victimized waitress and told her to get him a bottle of rum, on the house. Jack's eyes lit up and he smiled toothily, thinking this hadn't turned out that bad after all. Little did he know where this would lead.

"Captain Jack Sparrow," the bar keeper said to himself, remembering. "Captain of the cursed Black Pearl, feared throughout the Seven Seas and the one who with a single shot took out the undead Barbosa!" He exclaimed triumphantly. "Indeed, I had no idea we had someone that famous in our midst!" He seemed thoughtful for a moment. "Though now that you mentioned it, I remember you picking up a crew a little while back, to chase after the Pearl." Jack's heart and ego swelled up like a balloon to hear such compliments and he allowed for it to show in his voice.

"Aye, it is I." He said as though it were nothing special.

"A pirate of such magnitude must have good stories," the bar keeper continued. He always had a fascination with adventure stories and treasure hunting. He couldn't miss an opportunity to hear some real stories first hand from a pirate, nonetheless.

"Aye, some good ones," Jack said evenly. Even though the rum started to get to his head, he had learned his lesson about sharing too much information.

"Ghost stories!" Someone in the room cried out, and was soon followed by thumping and chanting of "ghost story, ghost story, ghost story!" Elizabeth looked at Jack expectedly. Ever since she was a child pirates and ghost stories fascinated her. Even though she was in one for a short while, it didn't quench her thirst. If anything it made her more adventuress. Will saw the look and sighed, rolling his eyes and smiling. If he is not careful, Elizabeth will get them both swooshed away in some adventure with Jack, to be sure. A dangerous one, at that. It was not that he didn't like adventures- he loved them, the excitement. It was in his blood. But he wanted also to settle down a bit, maybe even have children. And he would prefer to be on the adventure alone, rather than endanger his love, Elizabeth.

Jack chuckled at the chanting and nodded his head, getting up from his seat. He motioned with his arms for the cheering to be quieted down. He waited patiently until there was absolute silence and he had the crowd riveted, waiting. "A ghost story..." He said pondering out loud, enjoying toying with them. He paced slightly and seemed deep in thought. "I've heard and experienced and BEEN in so many, it's hard to choose." The crowd started booing, before Jack continued. "But," he said, calculating their reaction, noting how far along can he string them before he lost them. "But," he continued once they settled down. "I have just the one."

He jumped on the table in one quick motion that several people (including Will and Elizabeth seated at the table) gasped, caught off guard. He stood there crouching on the table with feline grace that seemed impossible with the amounts of alcohol previously consumed.

"The Legend of Sleepy Hollow."

He managed to get everyone's attention, including a visitor passing by who suddenly was VERY interested in the story.

"Now there's this little town, right on the Hudson river in central America," Jack said, his voice low, causing the people to sit closer and strain to hear. "It's called Sleepy Hollow, and indeed- it is a very peaceful and ordinary town, with one exception: It has it's very own ghost. The headless horseman." Some people gasped appreciatively, while others nodded and listened.

"Nobody knows for sure who he was. Some say he was a Hessian cavalryman who lost his head in the Revolutionary War. Others claim he is the commander of all the evil spirits in those parts. But the general rumor is that his body's buried in the churchyard and at night he rides out to the battlefield where he was killed to look for his missing head. He has to get back to his grave before daybreak." Jack took a swing of his bottle and dried his mouth on his shirt's sleeve. "But this story isn't about the headless horseman, though he may make an appearance towards the end. It is about the town's schoolmaster, Ichabod Crane. Young master Ichabod was the little twerps' schoolmaster and a learned man himself. He was in charge of the quire as well, and was paid with bedding and meals. He had a little and could carry it on his back and would pass his nights sleeping in each of the houses of the town.

He was good on the eyes, tall, wise, but most of all he had an appetite," Jack grinned. "Aye, he did. His thoughts were obsessed with food and money and one fair lady who combined them both.

"Katrina Van Tassel." Jack breathed in deeply, as though breathing in a pleasant scent.

"A beautiful lass, with a voice of angels. Filthy rich too, as opposed to him. Which is why it was no surprise he fancied her and went about suiting her. He could even picture the two of them with family, enjoying all of her family's fortune." Jack could see some people, though interested, were disappointed there were no ghosts yet. "Patience," he said, bringing his hands together in a silent prayer, before making fists of them, as he usually did. "The unnatural is before us yet."

"The lovely Miss Van Tassel was in the quire, giving Ichabod enough opportunities to compliment her singing and shower her with his educated mind. Trying to win her over by reciting poetry and philosophy. There was only one problem, in the form of another suitor:

Brom Bones.

Brom "Bones" Van Brunt was a bully and had a mean sense of humor. He and his lads had their fun playing pranks on the poor folk, who could do nothing about it. Brom had his eyes on that delightful trophy as well, and could not stand the time Ichabod would spend with Katrina. He tried provoking Ichabod to a fight, even trashing his schoolroom, but Ichabod knew better than to take to heart and to fight a losing battle. After a while Brom stopped and all was quiet for some time." Jack suddenly appeared to remember something and slapped his forehead.

"Aye, what a fool am I! I nearly forgot a crucial detail, such carelessness," he shook his head. "Ichabod, though a learned man, had a soft spot for ghost stories and witches. He would buy books and read them secretly, so no one knew. He was so caught up in his books that at times, walking near the forest at night he would hear noises, voices, calling: Iiiiichabod, Iiiiiichabooood". Gentle sounds in the cold. Once he even swore he heard hoof beats. Ichabod, not being particularly brave, would run for dear life, never looking back as he heard the footsteps running after him for a while until they ceased." Jack grinned, seeing how he won back their attention with the little detour of the story.

"Now, back to where I left off. One day at school, a messenger came bearing news of a party Ichabod was invited to, at the Van Tassels. Not wasting such a golden opportunity, Ichabod dressed up fancy and even borrowed a horse, trying to look respectable. He rode to the party with his head held up high, intent on winning over Katrina that night."

"Ahhh, such a party," Jack shook his head. "There was feasting and dancing and merry-making the likes of which you'll never again see. Ichabod stuffed his mouth full and even got a dance with his ladylove, right in front of the jealous Brom. It was a magical night, indeed. Stories proceeded, each having their very favorite. Brom himself claimed to have met the headless horseman. He said he offered to race him, but as they reached the bridge over the Hudson River the headless horseman vanished in a flash of fire."

As the party waned on, all the guests left, besides our fellow Ichabod. He was the last to leave and lingered to talk with Katrina. But the fickle Katrina had no intentions of being with Ichabod and she told him that Brom proposed to her that night and that she was going to accept. Poor lad! The way he stormed out of there that night, barely paying attention to the road, until he noticed how dark and cold it was getting. He picked up his pace and began to whistle nervously."

"Not before long he heard a loud groan. He spun in his saddle, but it was merely two limbs of a tree rubbing against each other. He urged his horse to move faster, which the stubborn thing refused to do! As he crossed a tiny stream he saw a shadow in the corner of his eye. He turned around and squinted, trying to make it out. He could make out a black and towering shape.

'Who-who are you?' Ichabod stammered, but the being did not answer.

'Who's there?" Ichabod repeated, swallowing nervously, his hairs standing up. He closed his eyes and rode forward when a loud noise startled him. He turned and saw the being approaching him. It came closer, and closer and closer still- until Ichabod could make out the being clearly. It was an enormous rider on a horse.

With his head under his arm.

Ichabod panicked, began riding wildly, with the rider hot on his trail. He failed to dodge him and in his frenzy saw the bridge looming ahead. He suddenly had hope and pushed his horse to ride faster, knowing salvation lay on the other end of it." Jack paused for dramatic effect and the crowd quickly "awwwww"ed him angrily to continue.

"He kept glancing back at the horseman, as the hooves of his horse clanked on the bridge. He held his breath as he heard the other's echoing hooves as well, until he finally reached the other side. He slowly dared to turn back...

The horseman was gone. He vanished, just as he was supposed to. Ichabod sagged in his saddle, breathing a sigh of relief. Suddenly the horseman rose up in his stirrups and hurled his head at him! Ichabod tried to dodge the horrible missile, but too late. It crashed into his skull! He tumbled into the dust and last thing he heard was the rider's evil laughter, cackling at him." Jack said and rose from his crouch, jumping down from the table.

"Wait!" Someone cried, "What happened to Ichabod?" Several other men joined in the question, until Jack was forced to answer them.

"He disappeared, vanished into thin air. The only thing left at that bridge was his hat and a smashed pumpkin." Jack answered evenly. "The town hired a new schoolmaster and shortly after his disappearance, Brom married Katrina. But somehow he always seemed to know something about the matter. Whenever anyone mentioned the pumpkin he would burst out laughing." Jack sat down at the table, before offering, as closure:

"What happened to Ichabod Crane, you ask? An old farmer claimed, a little while after the disappearance that he was still alive. That he traveled to a distant part of the country and went in to studying law. Farmers' wives were certain that some spirit had. taken the schoolmaster and he now haunted the deserted schoolhouse. If you would walk there on a summer night, you could hear a distant voice singing a hymn, the sound drifting sadly through the quiet of Sleepy Hollow." Jack finished and bowed: "And that, my friends, is the Legend of Sleepy Hollow." Many cheered, while several scowled on the merits of a ghost story without a ghost.

"That was a fantastic story," Elizabeth smiled. "I don't think I have ever heard it before."

"Nor I," Will added, quite impressed with Jack's story telling abilities. Though it was not as incredible as the story of your escape from the island you were marooned on, it was exceptionally good.

"I have heard the story before," a gruff voice said from the bar. "Though I have never heard it quite like that. No one ever knew what Miss Van Tassel told Ichabod that night." He gave Jack an unsettling look, like one weighing meat.

"Ah, it is the beauty of stories," Jack said lightly. "They have many versions."

"True," the man agreed, seeming to make up his mind. "Might I buy you a drink?"

"Need you ask?" Jack asked grinning. This was a good night, people seemed intent on getting him drunk. The man motioned for Jack to join him at the bar. Jack excused himself from present company and joined the stranger at the bar.

"You know, I come from Sleepy Hollow myself," the stranger said slowly, as he ordered a drink for Jack, who was beginning to not like this situation. He looked the man over, to see if he was a threat. He seemed in his mid to late twenties. ...

"Is that so?" He answered shrugging, though he was suddenly rigid.

"Yes. Such a coincidence, really. You see, Ichabod Crane was my schoolmaster, many years ago." He frowned, trying to think. "What was it... 19? Maybe 18 years ago, I still remember his face clearly. The day he disappeared he gave me quite a lashing." The man's eyes bore into Jack's. "But I'll never forget his eyes. He had such intense dark eyes, filled with compassion and mirth."

"Sounds like a fun man," Jack said, his mouth not quite twitching into a smile.

"Aye, that he was." He suddenly turned seriously towards Jack. "Sleepy Hollow is in need of assistance, the kind I'm sure a revered Pirate such as yourself can grant."

"Now why would I be interested in helping your fair town?" Jack asked, crossing his arms.

"It is haunted by the headless horseman." The man said gravely. Jack laughed nervously.

"The headless horseman does not exist."

"He does, he has killed people of our town and no one knows how to stop him." The man said nearly pleading.

"I don't know how to stop him." Jack said shaking his head.

"Ichabod Crane is the only one to face him and live," the man said, again searching Jack's eyes for a reaction.

"Well, as far as I know, Ichabod Crane disappeared that night," Jack smiled tightly, taking a large gulp of his drink and banging the mug down, spilling some on the counter. "And besides, he didn't face the headless horseman, it was merely a prank pulled on him by Brom Bones."

"How would you know that," the man asked triumphantly.

"This conversation is over," Jack said tersely. "Thank you kindly for the drink. Best of luck to you." He started to get up, when the man called:

"Katrina needs your help, Captain Sparrow." He said desperately. "The headless horseman murdered her husband."

"A tragedy, I'm sure," Jack drawled uninterested. "But I see no profit in it for me. And I ain't risking my neck without some sort of profit."

"She's offering a reward." The man said quickly. "How do ten bags of gold sound?"

"Now why didn't you say so before," Jack sat back down.

"Whoever manages to solve the mystery and stop the killings will win the reward. What say you?"

"I say- goodbye Tortuga, hello Sleep Hollow," Jack smiled widely. He suddenly remembered his deserted friends and he hurried over to them.

"It's about time," Elizabeth said impatiently. "We thought you abandoned us for that new friend of yours."

"I would never abandon such a lovely lady," Jack said crushed.

"Why thank you Jack," Will answered, pretending to be hurt.

"Well, you are almost like a lady," Jack replied easily. He covered his mouth with the side of his hand and asked Elizabeth quietly: "Is he a eunuch?" Elizabeth blushed slightly before whispering back, making sure that Will could hear: "Hardly, if you know what I mean."

"Why Mrs. Turner!" Jack exclaimed surprised. "How un-lady like of you!"

"She isn't," Will said teasingly, and receive a playful slap from his wife.

"Ah," Jack smiled widely. "I see I'm rubbing off on you, women can't get their hands off of you either." Will laughed at that and was soon joined by the other two.

"I'm afraid I must cut this visit short," Jack said sadly.

"I thought you gave your crew a vacation," Will said confused.

"I did. I have some business to attend to, I shall part with you now." He got up and bowed. "Do try and be a dear to an old pirate- do not let too long pass before we meet again." He walked towards the entrance. "And at least have the courtesy of inviting me to the first born's birth- I love children." He didn't take five steps out side before the two joined him.

"Where are you off to, in such a hurry?" Elizabeth asked excited, having a feeling he's off to an adventure.

"No where in particular," Jack said casually, hoping they wouldn't linger on the subject much.

"Then you wouldn't mind us tagging along." She said smugly, trapping him.

"What?" "What?"

Both Jack and Will asked at the same time, glancing at each other.

"You're heading on an adventure, aren't you?" Elizabeth asked, squinting her eyes suspiciously.

"And if I am?" Jack asked, crossing his arms.

"Then we want to join you!"

"We?" Will asked, raising an eyebrow.

"Will," Elizabeth turned to him. "You have pirates blood in you, don't you feel the sea calling to you, urging you to travel out there, seek treasures?"

"Yes, of course I do," Will sighed, wondering how to put this. "But not with you at my side." That possibly was NOT the way to put it. Elizabeth's mouth became a thin line. "Oh?" She asked enraged. "And why is that?"

"Having a woman onboard is bad luck," Jack threw in.

"Then why have Anne Marie in your crew?" Elizabeth retaliated.

"It is not that I do not want you with me," Will tried to explain. "It is simply that you are the future mother of my children! I cannot allow harm to happen to you."

"But you can allow harm to happen to you?" Elizabeth countered.

"It is different!" Will said shaking his head.

"Why, why is it different?"

"It simply is!" Will yelled exasperated, knowing it was a losing battle. "I couldn't bare to lose you."

"Nor I you," Elizabeth said gently, caressing his cheek. "Which is why we will go together, to allow no harm to come to the other." Will smiled at the wonder that was his wife and was about to kiss her, when Jack interrupted.

"That is all fine and well, but I have NOT said you are joining me." Before bowing and heading towards his ship. The Turners exchanged glances before hurrying after the pirate.

"Wait! Jack!" Will said. "Why can't we come with you?"

"It is something I prefer to do alone." He said enigmatically, rendering them confused. At the question in their eyes he quickly corrected himself:

"I don't wish to share the reward three ways."

"We don't have to have a part in the reward," Elizabeth said.

"No, no, no!" Jack said, resting his head in the palm on his hand and sighing. "What kind of piracy is that? No part in the reward!"

"Then you'll get most of it!" Will added, seeing an opening. "How about sixty-forty, for the two of us?"

"No!" Jack yelled and turned his back on them, walking towards his ship. The two followed close behind. "Sixty five-thirty five!"

"NO!" If anything he hastened his pace.

"Seventy-thirty?" Elizabeth asked, as they neared the ship.

"No! No! And if you missed the last one- no!" Jack said, turning back to them. "There is positively no way you are going to convince me to let you come with me on this quest!"

Will thought for a moment, before saying calmly: "You can't sail the ship on your own."



Author's Note: I apologize for the " being in the wrong place, but my Word is giving me trouble so I had to write this some place else and paste it here- and Word is still giving me trouble!

I got this idea even before I saw the Pirates movie, when someone in a fic mentioned Jack correcting someone's English ("To COMANDEER a ship") and I thought: wouldn't it be funny if Jack used to be a school teacher? Then: Wait, Ichabod was a schoolteacher! And the rest was further developed after watching "POTC" and "Sleepy Hollow" and rereading "The Legend of Sleepy Hollow." Right now it's a crossover with the novel, but I'm guessing it will also be a crossover with the movie, when he gets there to solve the mystery.

Any suggestions are welcomed. Does anyone know WHAT EXACTLY a Bootstrap is, and any clue as to why Will Turner Sr. was called that?

That's it for the first chapter, hope someone will enjoy it, I know I will.