(A/N: Gotta give a content warning for this one: there's a lot of depression, and sadness, a bit of sad drinking, and a mention of "unaliving" in this fic. I began writing this during a depressive episode so be warned. This was originally gonna be a one-shot, but it got way too long so I had to split it in two. I'm not gonna make y'all wait for the second part so the full story is up. All of the flashbacks are from various books in the young Jack Sparrow series. Btw a MASSIVE SPOILER WARNING for the entire series! Enjoy!)

Jack sat upon the deck of the Fleur de la Morte with his back against the starboard side railing and staring down at the ground. He wanted to be alone and out of the way from everyone below deck, and the Fleur's captain was in her cabin. He had also done the same thing aboard the Barnacle as the boat was so small that it did not have a cabin and Jack slept with his crew. Privacy was only a luxury when you were out at sea. During his days aboard the Barnacle, Jack sometimes sat on deck during the night to reflect on his life and his future. His thoughts were a lot more positive then than they were now.

"How dare ye start a fight in my father's tavern?" Arabella placed her hands on her hips and her brown eyes flashed. "Couldn't ye do your pickpocketing somewhere else tonight? Someplace nicer, whose patrons wouldn't wreck the place?" She pushed him against the wall and stepped back.

Jack brushed himself off, straightening the wrinkles in his coat. "Now, listen here, lassie, I am not a thief. I didn't come here by choice. And I wasn't pickpocketing," Jack waved the sack in Arabella's face. "Captain 7-foot-beastie in there stole my sack here, and I was simply reclaiming my property. So if my gratitude is worthless to you, I'll just gather up my things, not say 'thank you' for being so inhospitable, and be on my merry way. Savvy?"

"To adventure!" he toasted.

"To adventure," Arabella repeated, grinning.

"Yes, to adventure," Fitzwilliam said slowly and seriously.

"...and of course," Jack added, smiling, "to treasure...and freedom!"

"All right then, lads!" Jack said, grinning. "You, Fitzy—haul up the main sail. Arabella, make secure of the rigging over there. Tumen, try to figure out where in the blasted Caribbean we are. Jean, you take the wheel!"

"Where to, Jack?" Jean asked, grinning.

"Why, to find Left-Foot Louis, of course," Jack said, putting a foot up on the rail and looking out to sea. He adjusted his hat. "And oh," he added as an afterthought, "From now on, please remember...

"It's Captain Jack Sparrow!"

Since then, all of his crew left him to sail aboard the Fleur de la Morte with his old first mate's mother—all except Fitzwilliam P. Dalton III. He was Jack's snotty aristocratic crew member who annoyed Jack very much. Jack was not too surprised with the luck he had in life that the only person to not leave him, and to be left alone with, was the one who irritated him the most. Of course he later found out it was because the whole time they sailed together, Fitzwilliam was spying on him for the Royal Navy. Along with that, Jack's father, the Keeper of the Code, Captain Teague, found him a year after running away from home to forsake his family and their pirating ways. It all ended with the Barnacle being blown to smithereens, and thus leaving him back to where he started; ship-less and crew-less.

"The one you left has been looking for you," Tia Dalma said while she gracefully searched her canisters and containers.

"Oh, everyone's looking for me, love," Jack winked.

"But it is not all of them that you want to avoid—and the one I speak of is one who you do."

"Can't you ever just state something clear- and concise-like?" Jack asked.

Tia Dalma smiled. "Just be warned him came here looking for you. Him wants him ring back."

Jack gasped. Now he knew who she was talking about. And it was someone Jack really did not want to see. In fact, it was someone he had been running from for a while. Talking about it was giving him a knot in his stomach.

He turned around slowly, too stunned to put his hands in the air.

It was Fitzwilliam, and he had his rapier aimed at Jack's middle.

He looked much more relaxed than usual. In fact, his whole countenance had changed.

"We knew you'd lead us to him," he growled in a much deeper voice than he normally used.

"Fitzy," Jack said, honestly confused. "What on earth is going on here?"

But the other boy ignored him, continuing his rant. "'Pretend to be a teenage aristocrat,' they told me. 'Sneak aboard whatever boat they steal,' they said. I told them they were foolish to think you would ever lead us to him, but how wrong I was. You—a petty boy, who was not even a proper pirate."

"Hey, watch what you say about your captain," Jack said weakly, swallowing hard.

"Now we have both of you," Fitzwilliam continued. "Jack Sparrow and the most wanted pirate on the Seven Seas...the keeper of the Pirate Code, TEAGUE!"

The boy grinned nastily.

"Prepare to meet your fate, Sparrow. You and your dear daddy—if that rumor be true and he is the devil what spawned you—will both perish at the hands of the Royal Navy of England!"

"Get off my boat," Jack said, pointing his sword at Fitzwilliam's neck and breathing heavily in anger.

"Now, Jack..."

"I don't care where you go after you're off, but get off. Swim to the 'royal pains' back there, swim to the East India Trading Company slave ships, swim over to Teague and sail off in the sunset together. I don't care where in the devil you go. Just go. Now," Jack said.

Fitzwilliam stood shock-still.

"Now!" Jack yelled, raising his sword and bringing it down swiftly before Fitzwilliam. This caused the aristocrat to stumble, and as he lost his balance, Jack quickly pushed him overboard using the handle of his sword. There was a dull splash. Jack didn't look overboard. He didn't want to. He sunk down onto the deck, hugged his legs and buried his face in his knees.

He decided that throwing Fitzwilliam overboard was letting him off easy.

Jack lifted his sword, and an expression of terror formed on Fitzwilliam's face. Even in the moonlight, Jack could see that Fitzwilliam had gone pale. Jack smirked.

But when he went to bring down his sword, the most peculiar thing happened. Jack found that he was unable to move his arm.

He tried and tried, but something was preventing him from doing so.

Then he felt a tugging on his arm.

He turned slowly and found Teague standing there. The captain's hand was clenched tightly around Jack's wrist.

Just then, a rapid firing of cannons blasted from the port side of the ship.

Jack gasped, his eyes wide.

He had feared it before, but this time it actually happened—the cannon fire, meant for the Misty Lady, had blown the Barnacle to bits! He watched as his boat split into multiple pieces, the mast burning, the deck collapsing in itself.

Jack felt a very large lump develop in his throat, and, to add insult to injury, at that moment, he was whacked with a serious blow to the shoulder. His distraction had allowed Fitzwilliam an advantage. Jack fell to the deck, while all around him the battle raged between crews. Fitzwilliam smiled.

"I have waited, patiently, for quite some time to do this," Fitzwilliam said.

"Still, I was a captain before, and now—" Jack began.

"Jackie, let's be honest. That wasn't a ship, nor were you a captain," Teague replied.

Jack frowned, knowing that when all was said and done, Teague was right.

"But the Barnacle was mine. And my faithful crew—well perhaps the word 'faithful' is not entirely accurate—but I thought they were right fine sailors and a pleasure to sail with, except for that cat. And that aristo. A real, real pleasure. OK, maybe 'pleasure' is a bit of an overstatement."

"Jackie, boats, ships, crews—they will all come and go. You have yourself to look out for, and only yourself. That doesn't mean you don't do those things you know are right—specifically those things that are right for you."

If that did not hurt the most, it was afterwards when looking for a great treasure, Jack got stuck with a wash-up who seemed very odd, who Jack called Bloody Billy. He had unintentionally led Jack to the caverns of Poseidon's Peak and his old crew. Although he did not want to admit it, he was happy to see his old crew again. That was shortly until his former first mate Arabella seemed a little less happy to see him, and a little more happy to see Billy.

He never admitted it, but Jack had quite the crush on Arabella Smith. She had beautiful, long, tousled auburn hair, a pretty but tough face, and she was fierce. He liked that in a woman—a woman who wasn't so easy. She had made it clear that they were only business partners, shipmates, and best friends. That did not stop Jack from taking little steps to pursue her, but Fitzwilliam got in the way and did the same, leading to an argument and annoying Arabella. Nonetheless, Jack really cared about her no matter what.

Jack heaved himself and Arabella onto the Barnacle. He laid his shipmate down, and then, panting, he collapsed. His chest rose and fell as he regained his breath. As soon as his lungs were full, he knelt beside Arabella, who was pale, bloated, soaking wet, and what concerned Jack most of all—not moving or breathing. He opened her mouth and placed his lips firmly on hers, exhaling into her, willing her to breathe, determined to awaken her.

After all that, he thought, she can't have drowned. Not after all that!

Arabella coughed and sputtered, and Jack yanked her upright, pounding on her back so she'd cough up all the seawater she'd breathed in.

"Listen to me," Jack said gently. "Bell, put the Sword away."

"Don't call me 'Bell,'" Arabella said. Then, in a more sober voice, she continued, "you only call me that when you want something."

"I call you that because I know you. I know the sort of person you are. You wouldn't kill someone in cold blood. Not like this."

"That's how he killed my mother. In cold blood."

"And that's why you're not going to kill him. Because you're better than he is."

"Jack," Arabella said, "not long ago ye convinced me not to do something I'd regret, not to become someone—something—I didn't want to become. I only hope I can convince ye of the same thing. Just, please, be careful. I care for ye, Jack. We all care for ye." She kissed him on the cheek, gathered up the rest of the crew, and set off in search of shelter in the town below.

"On the whole, except for a tendency to prattle on and be a big know-it-all—" Jack concluded, a little more seriously—"which isn't entirely fair, since she really does seem to know it all—Arabella's the best first mate a captain could hope for, and a good friend."

It nearly killed him to be that straight, but Laura's eyes were wide and bright with gratitude.

"I'm not talking to her," she said before Jack could say anything.

"Bell," he said, sighing. "I'm not one to agree with Fitzy—ever—but she is your mum. My dad never even tried to talk to me. Maybe you should hear what she has to say. Then you can do whatever you want, and I'll stand by you. All right, lass?"

"Get out of here, Bell," Jack ordered, drawing his sword and facing the dragon.

"Not on yer life, Captain Sparrow!" Arabella cried indignantly. "When have ye ever known me to desert, eh?"

"Bell, I mean it," Jack said firmly.

Arabella stood for a moment, stunned by Jack's sincerity.

Finally, Arabella nodded and saluted Jack.

"I'll take care of the ship until you return, Captain," she promised.

"What?" Jack asked, confused. "What's wrong now?"

Her lips were quivering. For the first time ever, she looked unsure of herself. "Look, Jack, me and me mum, we sort of have to work...well..."

"You want to stay with her?" Jack said flatly. Captain Smith looked surprised.

Arabella shrugged plaintively. "I want to give her a chance at least. D'ye understand? I've never felt so free as I have with you on the Barnacle. I've never had such adventures...or friends before. And I feel so bad, especially after ye made me yer first mate and all..." She smiled at Jack for a moment, then squared her shoulders in determination. "But I've missed her so much...I don't want to lose her again. I'm going to stay with her and Mr. Reece on the Fleur de la Morte."

"Forever?" Jack asked.

"For now," Arabella responded.

A shadow of emotion flickered over Jack's face. "Well, do what you have to do, luv," he said softly. Then he shook himself and gave a fierce smile. "We're all free to come and go on the Barnacle. That's the point, is it not? We're all free to do as we please! Good luck with that, Bell!"

Jack noticed Arabella's eyes grow watery.

"You're crying, lass."

"Just something in me eye," Arabella said, throwing her arms around Jack's neck. "Thank you for everything, Jack," she sobbed. "You really are the best mate I've ever had—ever will have."

"Stars and saints! I thought ye were dead!" Arabella cried, throwing her arms open.

With a surprised smile, Jack opened his arms and waved as Arabella came running towards him—and the right past him, into the arms of Bloody Billy. As Billy and Arabella kissed, Constance coughed up a hair all disgustedly.

Ever since he lost everything, he felt that he had changed. The usually calm and cool and collected Jack Sparrow had grown a lot more angry since Fitzwilliam turned mutinous and the encounter with Man-Who-Might-Be-Father, often losing his temper. He felt terrible about it, especially for Tumen as his youngest former crew member seemed to be more afraid of him. It hurt to see the fear in the boy's eyes every time Jack lashed out. He had also felt a lot more sad, depressed, hopeless, and numb, and it was getting a lot more difficult to not show that in front of everyone, especially Captain Smith. That was why he was in the position he was currently in, sitting alone on the deck under the night sky fixed on the bottle of rum sitting between his legs with tears he fought hard to not let fall burning his eyes.

He wrapped his slender fingers around the neck of the bottle and held it. He continued to stare at the rum, conflicted on whether to drink it or not. He had not drank in over a year. He didn't have room to pack any drinks when he stowed away, and after spending years dealing with angry drunk patrons, Arabella would not have appreciated it if he asked her to steal a few bottles of rum from the tavern.

Besides, with all of his duties as a captain and being endlessly on his feet fighting vicious pirates and beasts, he wouldn't have had time to kick back and drink. But now, he wasn't a captain anymore. He was sailing under another captain who had a great cargo of rum for him to steal.

Jack popped the cork off the bottle and the strong smell of the booze escaped and filled his nostrils. His lips quivered as he stared at the beverage hesitantly.

Unable to fight the urge anymore, a single tear spilled out and cascaded down his face, followed by another, and another. Each of them dripping down his chin and jaw. A few of the tears had hit his lips, allowing him to taste the saltiness. He silently sobbed for a few minutes. When he gained composure, he wiped his face with his sleeve.

Finally making up his mind, he went for it. He took a deep breath and quickly brought the bottle to his lips. He chugged the rum, feeling the burn run down his throat.