Disclaimer: I don't own any rights to PotC, Jack Sparrow, Johnny Depp or anything…grr…but oh well…
Jack sat glumly in the crow's nest. Having told the lookout to get out and go to hell, he held an unobstructed view of the sea over which he was crossing. From his vantage point everything was visible—they'd just passed Jamaica and were now on their way to the British annex of Fort Royal. About which he was not happy at all. "If I had my way," he thought to himself, "I would have stayed in bloody Haiti and joined some voodoo cult. At least they know how to have a good time down there." Chin in hand, Jack scoped out the distance they had yet to cross. He figured they would make it there by nightfall. They would stay the night, to settle that stupid bet he'd made with what's-his-name Donahue, and then be off the following morning. A waste of time and of provisions.
Fort Royal—anti-pirate hellhole full of bourgeoisie, and the home of Elizabeth Swann—Elizabeth Turner, he bitterly reminded himself, a horrible name for a beautiful woman. She looked like a swan herself, with her lovely white neck and beautiful voice, and not at all like a turner—whatever the bloody hell that was. Jack withdrew a bottle of rum from his boot and took a swig. Situations like this, sometimes it was all he could do. The mast creaked beneath him and he looked down, suddenly aware of the height. "Goddamn it, it don't make no difference whether I die or no," he told himself. Feeling like a martyr, he put the bottle back in his boot. He had somewhat of a headache now—it was getting worse. He really did not want to go back to Fort Royal. It was his eternal destination—whenever he went to sleep or even closed his eyes, a view of the island popped up. A view of Elizabeth's house was ever-present, intangible and yet more real than his own ship. Instead of the lapping of the waves lulling him to sleep, he would hear the swish of Elizabeth's taffeta gown and the sound of her breathing. He would really not be surprised if he went to Fort Royal when he died, instead of hell. Actually that would be kind of his own personal hell when he came to think of it—he could probably stand mutilated limbs and eternal scorching fires pretty well, but just the thought of existing unseen in Elizabeth's house, unable to touch her or cry out, only able to watch her and Will—drove him insane.
He hopped down from the edge of the crow's nest and settled into the bottom, where all he could see was sky. That new crew member Donahue really got on his nerves. He was always throwing his weight around—all 120 pounds of it—and boasting about his conquests with treasure, women, and so forth. In addition to which, he was always after Annamaria, which privately made Jack laugh. He was pretty much entirely clueless if he had not observed by now that Annamaria was not interested, to put it mildly. He didn't worry too much about the only woman on board—if Donahue tried anything she'd stab him or worse. If he had been more like Barbarossa, for example, he would have had him walk the plank by now or worse, but somehow he found himself getting soft and compassionate. This distressed him greatly. A few nights before they had been drunk, talking and joking in the usual way. Jack had sworn on the grave of his mother that Elizabeth meant nothing to him, after Donahue had nosed around for details. What did she look like? How much taller was Will than Jack? Was she good in bed? The new crew member had bet him that if he really cared nothing for Elizabeth—an outright lie on Jack's part—he would be content to go back to Fort Royal for a night. Fortunately not even the stupid Donahue had pressed further than that, aware that if their presence was known all of the crew would likely be hanged. Of course, Jack had to go along in order to save face.
To know that Elizabeth was simultaneously so close and so far depressed Jack infinitely. He wished desperately that he could go back to his old self—the pirate captain who was always in control of everything, maybe make some more daring raids and take up with Scarlett again—but he knew this was impossible. He just didn't have the heart for it.
They were nearing Tortuga. Finally they could stop at dry land before continuing to Fort Royal, and most importantly air the crew out. Jack climbed down from the crow's nest and began pacing up and down the deck, barking out orders for mooring the ship and basically doing all he could to fill his captain's boots. He took over steering again from Annamaria and safely brought the ship into port. It was very easy to do—the Black Pearl was small and swift and very maneuverable. Jack looked up again at the black tattered sails and debated about whether to replace them or mend them—they impeded the ship's progress somewhat, but he didn't really care that much anymore and in any case fixing the sails would ruin the decrepit air of melancholy he preferred his ship to have—the melancholy that pervaded his soul. He heaved a melodramatic sigh and leaned against the mast.
He watched from the starboard as his crew left the ship, one by one. Annamaria cast an inquisitive backward glance at him. Jack told her wordlessly to go on. Finally they were all gone. Jack sighed and turned around, halfway decided to go back to his quarters and do something productive, and found Donahue standing inches behind him.
"Aren't you going to Tortuga?" Donahue asked him. His tone was not unfriendly, merely curious.
"I don't think so, Donahue," Jack replied, "at least not now. Why don't you go down?" The whores would love your company, he stopped himself from saying sarcastically.
"Aw, c'mon Jack," he said, "why don't we go down together?" Jack could detect concern in his features. Why not, he decided, why stay enemies with this young man? Holding grudges never helped nothing, that was one thing he'd found out after being alive 37 years.
In Tortuga he walked up and down the filthy streets, suddenly disgusted with the town he had frequented for so many years—all his life actually; he had picked his first pocket at the age of three on the adjacent avenue he was now facing. He turned and walked along the street and all his early memories came flooding back—there was the house where he had been brought up by his mother. She was an invalid and could barely take care of him since she was always so doped up. At any given moment he could find her in her bedroom, nearly invisible in clouds of opium. He had never really known her.
So, in lieu of his absent parents (his father, a pirate, never appeared in his life until he was 15 and spirited him away on his ship) Jack had made a life for himself on the streets. He'd taken up with a gang of street urchins in Tortuga and started stealing food and money, anything to keep himself alive.
Jack turned again onto a back alleyway. He passed a boarded-up building that, when he was young, had used to be a brothel—the very same place he had lost his virginity at 13. He didn't even really remember what the whore had looked like, only remembered her scent. Every so often he'd catch a whiff of a sugary-sweet aroma, sickening, like dead flowers boiled until they were candy.
He felt a sudden urge to get out of Tortuga, and fast. Luckily it was a pretty small town and soon he was at its border, facing the otherwise uninhabited island. Out here, in the fresh air, everything felt so much more pure. Jack had the fleeting thought that being in a place like Tortuga, where everything was bad and where everything had conspired to make him the rotten person he was, was a disservice to Elizabeth Swann and her radiant purity. No, it was Elizabeth Turner. The thought again came like a stab in the chest. Even though it was getting later and later and an unnaturally cold air swept over the Caribbean sea, Jack threw off his overcoat onto the grass and ran as fast as he could away.
Away Jack ran, over the hills and rocky faces that constituted the uneven terrain. He felt like he could run forever and never get tired. A kind of wild joy suffused him and then all of a sudden he was exhausted. He came to a halt, and feeling dizzy, gasped for breath. He put out a hand and to his surprise felt a rock wall. He looked up and there was a building that looked like a monastery of some sort—old, crumbling, forgotten. He decided to explore while he was here. He'd never seen this edifice before. It looked anachronistic and out-of-place on this island in the Carribbean. Like it belonged in Jerusalem or Baghdad or some such place. Not that he'd ever been to those far-off destinations, but no worries—he planned to.
Struck with curiosity, Jack walked around to find the entrance, a crumbling portico archway, inlaid with black stones and carvings that had partially fallen away. Upon closer inspection he saw strange faces that were almost rubbed out with time, but unmistakably there. They seemed to be watching him.
Jack was unnerved. What was this building doing here, in the middle of nowhere, practically? The thought occurred to him that if he died nobody would probably find him until much later. People might notice he was gone, but would anybody really care? He looked back over his shoulder and scanned the horizon for any sign of Tortuga, but there was none. He spun around again and one of the faces had come to life. It leered at him. Go on, Jack, it said, look all you want but you'll never find.
Donahue found him some two hours later, passed out in the middle of a wide open field. When Jack came to back on the ship, he blamed the illness on an excess of rum, leaped to his feet, kicked everyone out of his way, and resumed his position in the crow's nest, screaming insults at his crew at intervals. His greatest fear was seeing Elizabeth and Will together. His second greatest was going insane.
