Disclaimer: Don't own the world or characters, just this possibility
I haven't actually read any Pirates fanfic yet, but thanks to the friend who made me watch the movie with her three times, this plotbunny attacked and would not leave me alone until I wrote it up.
(Edit 11/05: As per my new policy, anonymous reviews get answered in my profile.)
"Insurance," he called it.
None of the other crew begrudged him his token, though after what they had seen none of them cared to do the same.
And it didn't affect him, as far as anyone could tell. He delighted in life and was outrageous in his eccentricities as ever.
Until on an overcast night, on a narrow, cliff-edged road on the way back from an eventful night at a tavern. No one could say whether he hopped onto the rocks bordering the path only for his ship-honed but drink-addled balance to finally fail him, or whether some less than charitable soul followed him in the darkness and took advantage of his state to push him. Either way, he was not as lucky as the governor's daughter had once been and the result was a 200-foot fall into the sea and a broken neck.
When Captain Jack Sparrow awoke, he immediately noticed three things.
First, the clouds had broken, and the moon shone down on the sea.
Second, he was no longer drunk.
Third, he was lying face up on a rock in the bay, periodically drenched by the spray.
And then he noticed something else that made him groan.
"Aww, not again."
It says something about the quality of the crew of the Black Pearl, their temperament, or what they had been forced to become accustomed to as a result of their captain's antics that none of them batted an eye when near dawn they heard muttering from a familiar voice accompanied by thumping and clattering up the side of the ship. Or when a dripping wet, ragged and skeletal Captain Jack Sparrow hauled himself over the side and stomped over to the wheel, pulling out his compass as he did so.
"Everyone to your posts!" he announced. "We're heading back to the island. I have a little…something I need to do."