Jack spent most of his first day back in Tortuga looking at ships. He had arrived on the island as a member of a pirate crew, but he wanted to be on his own again, free to enjoy the sea as he wished and become the captain of his own ship once more.
Since Barbossa had taken the Pearl from him, Jack had never really adopted another ship as his own as she had been. She was his first love and he felt that the moment he claimed another to be his permanently, he was betraying her. He was aware that no one really understood his passion for the Pearl. He had been accused by many as being overly dramatic in his actions and mannerisms since he had lost her and more than just a few rumors had been circulated as to whether he had indeed lost his sanity while stranded on that island. But Jack was never one to care about what people thought of him, the only thing that ultimately mattered to him was the Pearl and if it was the last thing he ever did, he was going to get her back.
In the meanwhile, he was biding his time, knowing that he would have to wait for the opportune moment if he were ever to see the Pearl as his own again.
So for many years Jack had done what it had taken to get by. He had sailed as a member of different crews and even captained more than a few ships of his own, but he never felt as he had with her. These situations were only temporary; a ship commandeered here or there to aid in the pillaging of a town that would provide Jack with enough plunder to get by, but nothing as grand as his adventures on the Pearl.
For him, the Pearl had been more than a necessary means to an end of riches; she had been his whole world, his entire life, and his truest love. Barbossa had taken all of that from him in mere minutes when the mutiny was committed and for that Jack could never forgive him. He would get his revenge someday and he felt in his heart that maybe the time was growing close. He almost felt as if the Black Pearl was calling to him, asking him to rescue her from her captor, and letting him know that soon the time would be right.
Jack thought that maybe the Interceptor was the key to beginning the long process of getting the Pearl back. If the HMS Interceptor was the fastest ship in the Caribbean (aside from the Pearl of course) it was at least a good start. He thought that maybe he could use her to begin pillaging towns as fearsomely as he used to, and then once he was one of the most feared pirates in the Caribbean again he would go after the Pearl.
For now, however, he simply needed a ship that would allow him to travel the short distance to Port Royal. He was looking for something smaller, something that he could sail by himself. Commandeering another pirate's ship was a dangerous thing in and of itself so he was also looking for a ship that was owned by someone who would not be extremely vengeful towards him if they were to cross paths again.
He had been at the docks all afternoon when just before dark he saw the Jolly Mon sailing in. It was perfect, so small that he was not even sure anyone would notice when it went missing. As it got closer to the dock, he realized the best detail of all…it was captained by a woman. She wore pirate clothes and had long black hair and beautiful dark skin. Jack did not miss the fact that she was very pretty as well and he left the docks with a large, rather crooked, smile on his face making a mental note to find out exactly who this woman was.