Bootleg or bootlegging usually refers to making, transporting and/or selling illegal alcoholic liquor or copyrighted material; the term originates from concealing Hip flasks of alcohol in the legging of boots. Bootleg may also refer to: Smuggling Rum-running, the sale or transport of liquor without regard to legal regulations and taxes Bootleg mining, hidden or illegal coal mining Bootleg (radio), the use of illegal equipment, frequencies, or operating procedures in two-way radio Bootleggi… (More on Bootlegging)