They butted heads from the very beginning, Sparrow and Turner had their reasonings and circumstances as to why they did, but after a while it seemed to be more of a convience than a game to William. They both knew how to play and often was either one step ahead of eachother or behind the other. He had met his match, at least to the outsiders point of view, that others thought that. But it was more of William simply taking the role of becoming a pirate than him being just a blacksmith in Port Royal. Events of course happened, things that could have either gone one way or another, but it still seemed to go all according to plan that was layed out before them all years ago.
The Captain was impressed though at how well William had learned and came into his own the more time he had spent with them. Despite the fact that he learned to betray him and yet at the same time acted of his own free will, he had quickly learned that the boy simply wanted to free his father all the while chasing after the bonny lass. It amused Jack greatly, especially when it seemed as the woman herself didn't even know who she truly wanted at first, and he simply enjoyed the show that was taken place before him. But at the end of the day, of every single day, the two always butted heads in some way or another.
He enjoyed the game however, seeing William and his inner dialogue of pining for something he always wanted and what he couldn't quite pertain at the same time. He knew that the whelp would pretend that Jack didn't know what he was talking about, that what he believed he saw and or noticed, was just his way to get under the man's skin. But as time went on, the more he realized one thing about the man; he didn't know what he truly wanted and was often lost on what path he needed to take. It concerned him of course, but it seemed like he didn't want to necessarily talk about it, even if he didn't ask him outright. He just knew how to read people afterall. Being in his line of work well... he just had that niche about people.
"You know, William, the more you stall on making the decision needed the more you stall on wanting what you want most in life and miss out on what's important. You can't always please others and pretend to be okay with it. Life isn't always going to give you a good hand."
The pirate told him as if he didn't already know this. Today was an off day, most of the crew was doing mild chores on deck, as he went about checking up on everyone. They were days from land, perhaps closer than any of them would realize really, but as he stopped and looked at the man before him, he wondered what was going through his mind that day.
"You seem troubled today, more so than usual."
Jack added as an afterthought, before bringing the bottle of rum up to his lips, and taking a swig from it.