Meanwhile on the opposite side of the Cayman Channel sailed The Black Pearl, calmly cruising along the sea with the crew quietly going about their duties. Jack Sparrow was deep in thought as it sat at the table of his private quarters, his arms were folded and his head lay against the table's edge. His father was busy taking in the room's luxurious trinkets, growing more and more jealous by the minute.

"Jacoby my boy; have I ever set foot in these premises before?" Caleb slurred, eyes crossed with complete bewilderment – glancing left to right, up and down and almost in circles like some captivated child.

Jack looked up and rolled his eyes at his odd, eccentric father. He placed an elbow on the table and rested his head in the raised hand, sighing with frustration.

"Yes Dad you have; once when you came to nose around before her maiden voyage and the second…the second was when Ruby-Rose stowed away from Maine and you came to bribe her off the ship – Remember?"

Caleb Sparrow took a moment to recollect the last cornerstone of his life before he retired from piracy it was becoming a father for the second-time. He recalled being somewhat reluctant to the task and was not surprised in the least when the young, mistrustful Olivia Arlington favoured Jack's presence more than his, for Caleb was guilty of expressing his initial disinterest in the child on more than one occasion..

"Ah yes I remember now, you came home from Singapore with some silks to trade. I thought there was something like a snake in the trunk you jumped up so quickly" Caleb chuckled heartily

Jack's grin was brief and weak, he had warmed to the memory of finding an infant peering over him from inside the trunk, remembering how the two of them just sat there looking at each other without a single word passing between their lips for the first thirty minutes.

"I dedicated too much in getting The Pearl back, I should have been there for her"

"The determination you had to get all this back would never have stopped, you would have grown to resent us I didn't want Live to see that…You're my son, I love you but you were right to leave when you did"

"Well I can't exactly turn back the clock but sometimes I wish I had that kind of power" Jack whispered regretfully

Caleb fumbled with his waistcoat, reaching for the inside pocket he took out a small navy-blue pouch and threw it in Jack's direction. Jack caught in and the force of the impact caused the contents to jingle as loud as sleigh bells. It was a noise he had not heard since he was a boy, playing out in the snow-covered English countryside years before the emigration to the West-Indies.

"What's this? I have plenty of my own loot Dad – this really is not necessary"

"Loot yes, gemstones and gold nuggets I doubt very much you have. What you are holding there is what I call my blackmail bag. Sure you can tempt anyone with money but it's easier with gems and far prettier to look at"

Jack dug his hands into the bag and was thrilled to feel the cold and jagged stones on his fingertips. He smiled at the tricks he father could still play on him and despite Jack Sparrow nearing 36 he still found himself in awe of his father. His thick brows furrowed as the infamous scoundrel slipped a finger into some kind of loop.

"Jewellery too, I bet it's no two bit piece either – What did you do, steal from royalty or something?" Jack teased as he peeked into the bag to take out the mysterious item. His father tried to stop him but the jewel was already clutched in his palm before Caleb could repeat the warning.

The delicate trinket was covered by Jack's thumb, he was puzzled by his old man's protests and was unsure whether he wanted to discover why. He looked at his old man that back at his thumb, slowly moving it away to reveal a large square-cut topaz and gold ring. Like a magpie, Jack was hypnotised by the splendour of the jewel and it's bright colourful sparkle. But a very sharp and protruding thought came to him. Jack had seen this ring before; it was worn by his mother Lilia.

"Is this anyway to treat my mother's memory? To store away a priceless item her engagement ring no less in a moth-eaten pouch…How could you do that Dad?" Jack fumed, changing from absolute calm to unflinching fury in the blink of an eye raising the ring with a clenched and angry fist.

"You watch your mouth, we may have not laid eyes on each other for six years but I am still your father who can and will whack you around the ear if an occasion calls for it. If you must know that ring has been safely placed away for the past sixteen years" Caleb retorted viciously

It had been a long time since Jack had been scolded, he was slapped across the face for being something of a roving womaniser but that was nothing he was not used to. But here he was shame-faced and guilt-ridden over his appalling behaviour towards his father and feeling the same vulnerability he had as a child.

"Then why, you cannot expect me to pawn this or hand it over to someone just to get out of trouble?"

"NO Jack look deeper into the pouch, there's something else I want you to have"

Jack cautiously obeyed his father and delved deeper into the purse, after sifting through emeralds and tiny nuggets of gold he came across a larger, much thicker loop and took it out. An anxious swell of emotion tightened around his heart. A picture was slowly forming in Jack's already troubled mind – An expectation that had never been discussed before was now out in the open. Jack was moved by his father's sacrifice but also felt ashamed as he could not do was being asked of him.

"Dad this is too much, I can't accept this…the man you wish your son to be does not exist. I'm a scoundrel Dad, a rough-neck I am certainly not the marrying kind" He pleaded

"Then keep it as a bargaining tool, the day your mother accepted that ring was one of the proudest of my life. But it means nothing compared to my daughter. When you find her use it to get yourselves to safety, nothing else matters"

Caleb buttoned up his waistcoat and placed his hands on his chest, he started out of the room with heavy, sombre footsteps. Reaching for the door handle he turned to his son who was staring at the jewel with the most serious expression on his face.

"For what it's worth Jacoby despite appearances and the short comings we are both guilty of. But that does not make me any less proud to have you as a son"

With that Caleb closed the door behind him; Jack sat there gazing at the orange sparkle of the precious gemstone. He was disturbed by the movements of his first mate as he shuffled in from the upper deck.

"Apologies Jack, but I thought it was high time I had a shot of the hard stuff, I believe it's important for a man to find a bit of peace every once in a while" Joshamee Gibbs' Cornish accent bristled over the silent gloom of the cabin. The noise wandered into his captain ears but it was not enough to distract him from his deep contemplation

"Agreed Mr Gibbs, the whiskey is by the bed" Jack replied after a long pause

"Ah you're a generous man Jack, thank you kindly" Jack said cheerily as he strolled to the bedside table, pulled the cork out with his teeth and guzzled down the potent alcohol.

"How does a leopard change his spots, when should an adventure find a happy ending…and why the hell a man does need a woman" Jack pondered quietly but Gibbs still could here what he said. Baffled and a little alarmed by his friend's odd sonnet Gibbs looked at the bottle of whiskey; it had not been touched then looked around for a glass there was none to be seen.

"Women are one of the best homecoming gifts after a long hard journey, there's hardly anything that can match the warmth and good company from the female of the species" Gibbs enthused, patting Jack on the back and sitting beside him. Jack seemed drunk and detached from his surroundings but he hadn't had a drop all day. Gibbs then noticed the gem that Jack had in his hand and was immediately intrigued.

"My mother's engagement ring, my father just gave it to me as a…gesture" Jack laughed to himself sarcastically, Gibbs became more curious but his stare gave no hint of being surprised, the gesture was easy to make a guess about – Anyone that saw Jack and Ruby-Rose would say the same: That they were a perfect match, that they were meant for each other. He could not understand the level of denial both pirates had on the matter.

"Three months ago I was stuck on a spit of land with nothing but my pistol, a huge cache of rum and the strangest aristocratic young lady I've ever known…I told her The Pearl was my life that it signified my freedom and it means everything to me. Now I'm not sure about any of it" Jack reluctantly explained

Gibbs did not know what to make of his Captain's vulnerability, the alter-ego of the showman had been temporarily cast away and there sitting beside him was the real Jack Sparrow; intelligent, sincere and also lovelorn. Gibbs knew that Jack Sparrow would never confess to it but it was there nonetheless and as was as plain as day.

"Well I'll leave you to it, but don't wallow in self-pity too long Jack you do have a ship to run"

"I'm fully away of that Mister Gibbs thanks for the concern anyway" Jack grumbled, Josh left to room to take charge of his duties. Jacked leaned against his chair and rubbing his eyes. He slammed his fist on the table and shook his head vigorously

"I never should have returned to Havana" He whispered