Being a privateer and a deck hand was one thing, but how did hook come across the jolly roger, become the captain of it, much less run across all the magical things he's have?
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Hook was a Captain and a pirate before the Jolly Roger back on the mainland, AKA, his normal time of which he originated. When he was 27, he took part of a Mutiny on the ship he served under, leading the way and killing the Captain in such an act that the crew respected him and made him the new Captain.
After that, he and a select member of the crew kept the ship and ran as pirates and privateers across the sea. Before Hook, he was known as Mutiny Red for a while, until he made a better name for himself and was known as Scarlet Jim.
That is until a strange storm in a strange part of the whisked him, his ship and crew into the waters of Neverland. The ship was all but destroyed, Smee helped rescue him from the waters and a very small handful of the crew, from the wreckage and the ship that Smee had, they build a new ship and named her 'The Jolly Roger.'