Jack had sailed on Teague's ship, Troubadour, as cabin boy throughout a three month journey. He looked forward to the trip not because he liked sailing with Teague, but because he hadn't been out at sea in months. Jack loved being out on a ship, feeling the rolling of the waves from below his feet, and the smell of the sea. Even though he was on Teague's ship, something felt right being there. After all these years, he still couldn't put a name to this exact feeling. Teague was mainly a "sit-at-home pirate" so opportunities to go out to sea were quite rare for Jack. Once in a while, he would have the opportunity to employ onto other people's ships.
He loved being on Borya Palachnik's ship the most. As a lad, he used to pick up pocket money by during chores aboard his assortment of Koldunyas. He remembered when Borya would always ruffle his hair and praise him for being a smart boy. Jack had never received much in the way of approval growing up, so those words had stayed with him. Being older now, Jack finally started to sail aboard Koldunya with her crew. Her captain, Borya would still ruffle his hair and praise him like he always did. At night, he'd let Jack join his crew in singing sea shanties and drinking with them, which was something Teague would absolutely never allow him to do and Jack always kept that a secret from him. Borya always treated Jack as an equal to his crew unlike Teague.
Even after being on and off ships practically his entire life and trying to prove he can be out at sea, Teague still never saw Jack being fully ready to sail out at sea officially part of the crew of the Troubadour and he never failed to constantly remind Jack of that. Sailing on the Troubadour meant not only he had to sail with Teague who constantly reminded him how he was destined to fail, he also had to sail with his cousin, Valerie.
Valerie constantly terrorized Jack throughout his whole life. He remembered being as young as the age of three when she would shoot him in the head with a slingshot and lock him in a crate for several hours while Teague was frantically searching for him. Many of Jack's other memories included Valerie burning his hands with a candle, stabbing him with pins, putting leeches in his bath, breaking his finger when he was nine, spiking his food with chili peppers, throwing hard tacks at his head, locking him in the cargo deck until somebody noticed he was gone, and the numerous times she's thrown him off of ships and pushed him off the docks. Valerie always burst into a fit of laughter at Jack's expense. However through all the torture she had put him through, Teague always respected Valerie as a pirate much more than he did with Jack. Jack's face always twisted into cringe every time he heard Teague praise her.
"Oh, in the name of all that is blessed and blasted, could you stop this sweety-sweety 'Nice job Valerie' already?!" Jack yelled out at Teague. "I feel like hanging my head over the railing and blowing my guts out!"
"You're just jealous because Teague never says anything nice to you!" Valerie snarled.
"I don't even know why you're here anyway, women are bad luck on ships!" Jack said turning to Valerie.
"So are little bratty pirate boys!"
Jack and Valerie growled until they heard a loud bang. They both looked up to see Teague looming over in between them, holding a pistol up in the air with smoke coming from the barrel.
"Enough!" Teague demanded. "Jackie, go below decks right now."
"What?! Why me?! If anything she should be sent down there! She butted in!" Jack ranted waving his hands around.
"GO!"
"I HATE YOU!"
Jack stomped over to the opened hatch. Before storming below decks, he turned to see Valerie, still with Teague, with a wide smirk across her face.
Jack leaned onto the railing at the bow of the ship watching Shipwreck Island grow closer and closer. The ship carefully steadied its way through Devil's Throat and the tower of hundreds of ship hulks came into view. The evening lights shone beautifully throughout the island as the city was active no matter what time of the day since Shipwreck City was not known to have day or night hours.
The ship docked and Jack watched all the people by the docks and going up the streets of the city. All pirates with scraggly patchy beards, worn bandanas or tricorns, and faded waistcoats and trousers. Some of the people Jack happened to catch his eye on while people watching were quite amusing to watch. Some picking fights with others just because, some too drunk to even stand and throwing up on the street, some who just look plain weird in general. The one person who drew Jack's attention this time around didn't fit into any of those categories. It was a girl who stuck out from the many other pirates around her. She had beautiful, long, wavy brown hair, slightly tanned skin, a chartreuse green dress, and she was built not incredibly skinny, but not overweight either. She did not look like she belonged here.
"Jackie!"
Jack snapped back into reality and quickly turned to Teague who was waiting impatiently on deck by the gangplank.
"Come on, boy," Teague said impatiently. "Everyone's already left and I've got to close the ship."
"Alright, alright! I wasn't going to stay here forever. Don't rush me!" Jack blurted out, clearly annoyed.
Jack hopped off the gangplank and followed Teague through the city to the Great Chamber. He couldn't keep his eyes off this girl as they walked by from a distance and the girl seeming to be in too much of a rush to notice him.
Teague and Jack walked through the door of the Chamber and went upstairs in the back to the living area. Teague disappeared into the room and Jack took a deep breath and went in after. Entering into the room, he dodged to the left when just like that, a knife whistled just past his ear, so close that it cut the edges of his hair. Jack looked behind him to see the knife stuck into the wall.
"Oh, hi Grandmama," Jack said flatly.
Growing up, he learned by instinct to always dodge or duck whenever entering into any room in his home. Grandmama was known for hiding knives in all different pieces of her garments. Like as if she hadn't just narrowly missed killing Jack, she sat contently in her rocking chair. Her feet and wooden cane tapped on the floor after every rock and she stared at Jack with a cold, blank stare from her sharp, black eyes.
"I see you're back again...alive," Grandmama snorted, in her strong, husky voice like always.
Others in the family were in the room as well. Teague was seated on the side of the couch closest to Grandmama with the prison dog resting by his feet and the ring of keys hanging from its mouth. Brannigan and Uncle Jack were also seated by the couch, Uncle Jack having passed out from the drink. Another couch sat Aunt Hazel and "Quick Draw" McFlemming.
All the sudden, McFlemming's children came out from their hiding places and jumped onto Jack's legs.
"Jackie's home!" The children cheered. Jack never found them to be extremely pleasant.
"Argh...come on kids. Get off the whelp now," McFlemming uttered.
"Err...don't mind me, family. I'm just going to get a snack and go up to my room. It'll just be like as if I had never came back home...alive. Savvy?" Jack said urgently trying to get out of everyone's way.
Jack shuffled around the little cousins and went around the back of the living room to where the kitchen was. He went up to a cabinet hoping to grab something to munch on when another knife flew past him into where the cabinet shut, preventing Jack from opening it.
"Oh, come on! Could I just eat anything around here without being nearly killed for once?!" Jack snapped. He turned around to see it was Valerie who threw the knife.
"I see it took Teague's whelp a while to come back," Valerie sneered. "I came back here about an hour and a half ago."
"I was people watching! So?" Jack reached over into another cabinet and grabbed an apple. "Jokes on you, there's more than one of these here."
Jack took a bite out of the apple, and walked past Valerie to the stairs. Before reaching the top, he stopped and looked down at his cousin.
"One more thing, could you all please stop calling me a bloody whelp?! It's getting pretty old by now!" Jack complained.
Jack continued to the top of the stairs and went down a small hallway leading to the bedrooms. Before he could reach his room, Mabeltrude, the family visionary, jumped out in front of Jack, making him startle and almost choke on a piece of his apple.
"WELP OF TEAGUE! I CAN SEE IT NOW! YOU EYE FOR SOMEONE WHO WILL LEAD YOU TO YOUR GREATEST DESIRE!"
"Ugh. I don't need this right now," Jack grumbled as he pushed past her. He went into his room and locked the door.