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While the term bootlegging likely entered the lexicon of American slang many decades earlier, it is chiefly associated with the illegal production, distribution, and sale of alcohol during Prohibition (1920–33). The precise origins of the term are somewhat vague. Many sources suggest the term dates to the 19th-century American west. Others extend the provenance of the term as far back as the 17th century. Most concur that the term derives from the practice of secreting contraband (or other items) in the top of a tall boot leg. While predominantly a reference to illegal alcohol trafficking, it now enjoys popularity as a way to describe many forms of illegal trading in copyrighted, trademarked, or otherwise protected forms of merchandise.

Prohibition began with passage of the Eighteenth Amendment to the U.S. Constitution. Section 1 of the amendment states, “After one year from the ratification of this article the manufacture, sale, or transportation of intoxicating liquors within, the importation thereof into, or the exportation thereof from the United States and all territory subject to the jurisdiction thereof for beverage purposes is hereby prohibited.” With this one sentence, the impetus was given to establish a vast underground network of alcohol sales and distribution. Far from quelling the American appetite for intoxicants, Prohibition merely drove underground and arguably solidified alcohol consumption as a part of national culture.

In its original sense, the enterprise of bootlegging alcohol in America extends back to the beginnings of the nation itself. The right of rural settlers to manufacture alcohol and the power of the government to collect taxes on production fueled violent clashes throughout the hills and backwoods of early America. The inevitable conflict between individual enterprise and governmental “intrusion” via taxation was something the Scotch and British immigrants to America knew all too well. Whiskey had been taxed by European governments as far back as the mid-1600s. By 1700, the British had coined the term moonlighters for the brandy smugglers on the coast of England. In the American colonies, the illegal distiller came to be called a “moonshiner” or “bootlegger.” The United States collected an excise tax on alcohol from 1791 to 1802 and then again from 1813 to 1817. Alcohol production was untaxed for the next 45 years, but in the midst of the Civil War, Congress again passed a whiskey tax. By 1865, the tax on whiskey was $2 per gallon. This rate of taxation amounted to as much as 12 times the actual cost of making a gallon of liquor.

Illegal production and distribution of alcohol was not a strictly rural phenomenon. Individuals in urban centers likewise developed their own culture of organized crime and violence revolving around the illegal importation and sale of untaxed or prohibited alcohol. In the cities and along the national borders (including coastlines), illegal alcohol trade centered on methods of undetected importation and promulgation of venues for sales (i.e., underground clubs or “speakeasies”). Competition between rival factions seeking to dominate or monopolize particular territorial interests eventually fomented the formation of what would become long-enduring organized crime syndicates. In contrast, rural areas tended to support a yeoman culture of covert production (i.e., “moonshiners”) and overland distribution (i.e., “running”) to cities and other distribution points.

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