After the unfortunate collision of Bleak's chair and Jack's head, Jack laid unconsciously sprawled on the floor of Tortuga Inn room 17 for three days. Once the pirate came to, he had not a single inkling as to what he was doing there or even who exactly he was. As soon as he had gathered what he assumed to be his personal effects and put them on, he wandered aimlessly into the hall and followed the stairs down into the lobby/dining area. The bartender, who dropped his glass upon sighting him, appeared to be less than pleased to see Jack.
"You owe me two nights' fare fer that room!" He demanded.
Jack smiled apologetically and searched his pockets for his coin purse. "I'm sorry, but it appears that I don't recollect ever being there that long. Now that I think of it, I don't remember much of anything."
The old man visibly reddened with anger. "You've already tried that one! If you couldn't come up with a better story than that, why didn't you just sneak out like you did last time?"
Jack frowned. "I left without paying? By all means, I'll recompense. Tell me, how much do I owe you for this stay and the last?"
The bartender smiled to himself and picked up another glass, nonchalantly drying it. "You really don't remember anything, do you?" Jack shook his head quickly. It certainly was uncharacteristic of him to offer to pay for anything, much less what he had previously stolen, the old man decided. "All right, then, I'll settle your account fer . . . six schillings."
Jack nodded and opened up his coin purse only to close it quickly and give the old man a shy smile. "I don't seem to know how much that is." He handed the purse to the bartender. "I'll trust you know how much it is, good sir."
The old man took the small bag from Jack and craftily removed eight schillings. He smiled and handed the satchel back. "Have a good day, Captain, and do come see me again."
Jack smiled happily at the man and nodded. "Indeed, sir! You have a lovely day yourself!" He staggered uneasily out of the inn. Had he always walked with such unsteadiness?
Jack took the street that met the inn and held fast to it. He hoped that if he walked long enough, he might come across someone he recognized, or better yet, someone that recognized him. That bartender called him captain, he might have been able to tell him something. Too bad he didn't realize that while he was still at the inn. His head was too busy humming with pain for him to concentrate on much. He turned around, deciding to make his way back to the inn, only to find it was lost amid the hordes of people.
Jack spent the several months of what would turn into years wandering around the island of Tortuga, asking questions and beseeching help. He was met with no answers and much frustration, and soon people began viewing him as the island nuisance. (A/N: Ok, maybe it's unlikely that no one had a clue who he is, but let's just pretend.) Once his finances were tapped, which was very quickly thanks to his inability to count, he sought employment and found a job working security on the docks. This kept enough money in his pockets to keep clothes on his back, a roof over his head, and food on the table, but little more, and sometimes only the better two of three.
After losing about fifteen years and thirty pounds, Jack decided he'd had enough and took to plotting his escape from the island. He watched the ship schedules very carefully for about three weeks and finally found the perfect vessel to stow away on. Its destination: the quaint island of Anguilla (A/N: I just picked a Caribbean island, mkay?).