Etymology

bootlegger

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Today it means: One who is illegally a producer and/or trader of goods, especially of alcohol. Full definition →

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The story

From bootleg + -er. Originally a nickname given to smugglers in King George III's reign, derived from the smugglers' custom of hiding packages of valuables in the legs of their large sea-boots when dodging the king's coastguardsmen.

Etymology from Wiktionary, CC BY-SA 4.0.