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More back story for you...

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Jack woke on the cold stone floor. He was confused for a few moments, but when he moved, the pain returned along with all his memories of the past several days. Rolling carefully from his side onto his back, Jack recalled how he'd come to find himself in a familiar situation...

Jack had bumped into Capt. Askew (almost literally since he was quite drunk and thus reeling slightly more than usual) in a tavern. Will had been away (collecting information as Jack found out later) and Jack had somehow found himself conversing seriously with a man who had tried to kill him when last they'd met.

Against his better judgment, Jack had agreed to join up with Captain Askew and his ship, the Black Calamity, so that they could combine their efforts to overtake a small merchant fleet headed through the area. If all went well, both men stood to gain a lot of booty with minimal effort. They'd agreed on placement of the ships (the Pearl hidden in a cove to the east and the Black Calamity waiting in open waters to the south). Like wolves they would circle the small fleet and overtake it.

An accord had been struck and plans set to have the ships in the set positions in one week's time, when the fleet was scheduled to arrive. Jack hadn't completely trusted Captain Askew, especially in light of the fact that the man had caused him considerable problems when they'd last met some 10 years ago. Of course, Jack had also given Capt. Askew his fair share of grief in return.

But Jack wasn't in the same position as 10 years ago. He had the Pearl and the support of his faithful (inasmuch as pirates can be at any rate) crew and he was certainly not as naive as he'd been back then. Still, he knew in the back of his head that the arrangement wasn't a particularly good idea. What had seemed smart in the middle of the night, with far too much rum under his belt, struck Jack as rather foolhardy the next morning. By then, both pirate ships had gone their separate ways, and Jack was hesitant to mention his arrangement to Will.

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"I don't understand. Why didn't he tell me all this?" Will asked Gibbs. Gibbs had been filling Will in on things. The Pearl was sailing right to Grey Spot Island, rumored to be the island Askew used as a hideout.

"Couldn' tell ya, Will. But I figure he didn' think you'd approve of his arrangement with Cap'n Askew."

"And why's that?"

"On account of what happened last time Jack found himself tied in with the man..."

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Jack squirmed around a bit on the cold floor and again cursed his stupidity at having been caught. He'd decided to not tell Will exactly why the Pearl had to be in the exact spot on that particular day. Just to avoid discussing it, he'd given Will full charge of plotting their course over the week prior, which the young man had done especially well.

Upon their arrival at the cove, things had gone badly. The Pearl was a fast ship and very maneuverable for her size, but Capt. Askew was clearly more familiar with the waters in that area. He'd trapped the Pearl by blocking her in. The land formed a natural bay shape so the Pearl became caught between the curved land and the Black Calamity. Just as the crew of the Black Calamity had begun to storm the decks of the trapped Pearl, an unexpected arrival had occurred. The fleet that was supposed to be relatively unarmed had been escorted by several small yet heavily armed ships of the Spanish Navy.

Chaos had broken out, and somehow both the Pearl and the Black Calamity had escaped. The Pearl had sustained minimal damage and had easily out run the other ships. There was only one problem – she was minus her Captain. As fate would have it, the moment the Spanish ships had appeared, Jack had been onboard the Black Calamity engaged in a sword fight. He was on the far side of the deck and was as cornered as his ship had been. Though the rest of his crew that had been onboard the opposing ship had managed to swing back to the Pearl, Jack was stuck. He'd waved off the Pearl, knowing that if they remained on his account, the ship would have been caught, or worse yet, sunk.

Although the Black Calamity had been damaged, it too escaped. Jack had been immediately tossed in the brig and ignored since the Captain was much more concerned with limping his ship out of the area to do repairs on her. It had been almost a day by the time Jack was dragged off the ship onto the Grey Spot island. He'd made a valiant attempt to escape his captors, but unfortunately, luck was not with him for a change and Jack had been on the receiving end of more sword stabs and cuts then were absolutely necessary. By the time he'd been hauled in to see Capt. Askew, he'd known he was in trouble.

Rolling over yet again, still searching for a more comfortable position (though there was none to be had), Jack felt his shoulder wound throb. It's proximity to a much older scar almost amused him. Almost.

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"What? What happened last time Capt. Askew got Jack?" Will asked as Gibbs paused. He was silently cursing Gibbs style of dramatic storytelling and wishing the man would just get on with it. There really was no need to draw out the tension like it was just some barroom tale.

"Now remember this happened just before I met Jack. He'd just lost the Pearl and was still tryin' to get 'er back. He tried to lure Askew into chasin' after her, taking him with them. After telling him about the treasure of Isle de Muerta, Jack'd certainly got the man's attention. Problem was, Askew wasn't interested in goin' after the Pearl. Jack had tried to bargain with the man to give him half the treasure in exchange for helping him regain control of his ship. But Askew figured there wasn't need to get the Pearl to get the treasure; afterall, the only thing he needed was someone who'd been to the island before to find it."

"Jack."

"That's right. But when Askew pointed that out, Jack said even he couldn't get to the island without a map, a map that was hidden onboard the Pearl. Well ol' Jack kept them chasin' after the Pearl for ni' on three months before one day, Cap'n Askew finally lost his patience. He tied Jack up and beat the livin' hell outta him right there on deck, an' then demanded he figure some other way to the treasure. Well Jack said he'd had the map all along, hidden in his effects, and seein' as he was surrounded by Askew's crew and on board the Black Calamity, they untied him. Jack pulled out a map and gave it to them, then jumped overboard into the ocean.

"He jumped overboard?"

"Well, almost. More like he was stabbed and conveniently fell o'er the side I imagine. But, you know, if ever he tells the story, he escaped unharmed doing a swan dive o'er the side. Anyway, somehow the crazy bastard swam ashore on Tortuga an' that's when I met him. He was still bleedin' pretty bad, and looked like a half drowned rat, but you know he was still smiling. Even as I dragged his sorry, bloody carcass up the beach, he was laughin' his head off."

Irritated by yet another one of Gibbs storytelling pauses, Will prompted, "Well ... why?"

"Cause that map he gave Askew wasn't to the Isle de Muerta."

"Where was it to?"

"The finest whore houses in Tortuga!" Gibbs finished with a laugh of his own. "An the best part is even though he knows Tortuga like the back of his hand, Jack's been complaining about losing that map ever since."

"Sounds about right," Will said with a shake of his head. "You said he was stabbed?"

"Aye, you know that big scar on his left shoulder?" When Will nodded Gibbs continued, "That was courtesy of Capt Askew. I'm figurin' that's why he didn't want to tell you his arrangement with Askew – figured you'd worry too much, seen' as how he has that little reminder of his last encounter with 'im."

"Why would he do something so stupid? Why make deals with a man like that?"

Gibbs shrugged. "Maybe to prove to himself that he can still get the best of ol' Askew?"

"Maybe because he thought he'd have the Pearl to protect him, that he'd have me to help protect him," Will said, the guilt making him sick. During the attack, Will had been onboard the Pearl, defending the ship. There had been no way for him to help Jack, not from his position, when everything had gone wrong.

"Hey now lad," Gibbs said. "There was nothin' we could've done just then. I've been on the waters for longer then I can remember and I've never seen an'thing like that mess. We did what was best, what Jack wanted."

"What? Leaving him with that bastard Askew because he fell behind?" Will said loudly as he got up and began pacing the room. He could still see Jack waving them off. Even so, it felt like betrayal. He'd watched as the man he now knew was Askew had grabbed Jack and hauled him away.

"No, doin' just what Jack wanted. You saw him signal clear as I did. Now we've got to do it, finish what Jack wants."

"You mean I do," Will said, stopping to face Gibbs.

"Aye, 's time for you to be Captain of the Black Pearl."

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tbc...