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Initially, bootlegging was a term for people who carried flasks of liquor on their bodies, in rounded bottles that strapped to the calves of their legs, where the bottle would be hidden by their boot and yet easily accessed. Soon the term was used to identify anyone who transported alcohol over land.

Rum runners made use of the fact that liquor wasn't banned if more than 3-miles offshore. People who owned small boats would meet larger boats carrying liquor in legal waters (usually in the dead of night) and transport the alcohol to shore, where it would be sold to bootleggers.

These two terms quickly became synonymous to describe people who transported liquor illegally.

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11y ago
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Q: What is the difference between bootlegging and rum-running?
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