In a time where you could be an honest farmer or ruthless outlaw, Jack Shepard chose the latter. He liked the idea of roaming and never finding a home for too long and using his charms and intimidation to get what he needed to survive.
He was okay at it with just a few robberies and knock overs jobs that got him a little fame. He did it all and walked away with everything until word got to Jack that he was captured, tried, and hung along with the secret of his loot.
But rumors came as to a map that Luke had that showed where he hid his riches. A map that Jack so happened to win during a poker game one night. And by "win", he just bought drinks for his opponent until he passed out and Jack walked away with the money, free drinks and the map.
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