Bootlegging, the unlawful transportation or distribution of any article, but particularly alcohol. The word originated in American colonial days, when the sale of liquor to Indians was outlawed. Smugglers hid liquor-filled flasks in the legs of their boots and sold the alcohol to the Indians. The words bootlegging and bootlegger were derived from this practice.

Bootlegging sprang up again in the mid-1800's when parts of the country began to adopt local and state prohibition. It soon became a profitable business and was practiced extensively after national prohibition became law in 1919. Alcohol manufactured in foreign countries was smuggled into the United States. Home-manufactured alcohol, called moonshine, was secretly distributed. Large-scale bootlegging ended with the repeal of prohibition in 1933, but the bootlegging of moonshine—which is cheaper than legal alcohol because no taxes are paid—continues in some rural areas.