Rum-running, or bootlegging, is the illegal business of smuggling alcoholic beverages where such transportation is forbidden by law. Smuggling usually takes place to circumvent taxation or prohibition laws within a particular jurisdiction. The term rum-running is more commonly applied to smuggling over water; bootlegging is applied to smuggling over land.

It is believed that the term bootlegging originated during the American Civil War, when soldiers would sneak liquor into army camps by concealing pint bottles within their boots or beneath their trouser legs. Also, according to the PBS documentary Prohibition, the term bootlegging was popularized when thousands of city dwellers sold liquor from flasks they kept in their boot legs all across major cities and rural areas. The term rum-running was current by 1916, and was used during the Prohibition era in the United States (1920–1933), when ships from Bimini in the western Bahamas transported cheap Caribbean rum to Florida speakeasies. However, rum's cheapness made it a low-profit item for the rum-runners, and they soon moved on to smuggling Canadian whisky, French champagne, and English gin to major cities like New York City, Boston, and Chicago, where prices ran high. It was said that some ships carried $200,000 in contraband in a single run.