The luckiest pirate, or the most unlucky. The worst pirate one may have ever heard of, or perhaps the best. You decide. Either way, Jack Sparrow once made his mark deep within the Caribbean seas at a young age.
Legends speak of his bold and daring adventures. From sacking Nassau without ever firing a shot, to surviving three days marooned on an island only to finding civilization again. It would appear that this witty pirate was indeed hard to capture and/or kill. In reality, Jack was witty, with a rather questionable morality, and hardly ever sober. In his hand, there was almost always either a jar of rum or a mysterious magical compass which may never have pointed north, but rather to things he desired most.
And what would a pirate want most in life? To be able to sail free under his own flag. Free from the fear of the deep, crushing oblivion of death. Sparrow in fact searched long and far for this mysterious power. From finding ways to escape his own execution with the help of the legendary Davey Jones, to seeking the lost Aztec gold which cursed men with a half-immortality. Each endeavor however included a fate far worse than its own reward. A monkey's paw in disguise of the ultimate gift at best. And each time, Sparrow had a chance to nab immortality, he almost immediately disregarded it soon after, as he did not want to be bound by some horrid curse.
While Jack has had the pleasure of commandeering many ships in his time as a Pirate and a captain, Jack's most infamous vessel was in fact, the legendary Black Pearl. A charcoal-black vessel with black sails. It's true origins state, that she was once a slaver's vessel, whom Jack had the opportunity to captain. But instead of wanting to enslave others, he set them free, only to have his new vessel be blasted out of the water, giving its wood that distinct smoldered look. But, Jack survived and made a deal with the devil. To Davey Jones, he wished to resurrect the Pearl from the depths, and be its captain for thirteen years, then to serve the captain of the deep for a hundred. It was however a ploy and a race against time to beat Davey at his own game from then on.
Legend has it that the Black Pearl's captain and crew were so evil. that hell itself spit it back out into the mortal world. But those tales came from survivors of their brutal plunders. But, in reality, the Pearl's crew had been searching for a cure to what cursed them with their immortality. The Aztec Gold. Sparrow in his quest for immortality inadvertently cursed his men when they took the gold and sold it for a hefty profit. While his men suffered from the curse, he did not. As he was soon mutinied by his first mate, Barbossa. For the next few years, the two would be in a jockey for power and command of the vessel until Barbossa met his end.
Once more, the Pearl and Jack would meet their end at the hands of Davey Jones as Jack's time was up. But he defied Jones, and so his life was forfeit. In one final battle, Davey's personal pet, the Kraken crushed and devoured the vessel, sending it to a pocket-afterlife like existence known as the Locker, where Jack and his ship spent several months until his former crew was able to save him.