Researching a novel and several stories with scenes during Prohibition, I wondered: What’s the difference between rum-running and bootlegging? The former is usually applied to illegal shipments of alcohol over water; the latter to transporting booze over land. The term “boot-legging” arose during the Civil War, when soldiers smuggled liquor into camp by concealing pint bottles inside their boots. The word became popular (and lost its hyphen) during Prohibition (1920-1933) when suppliers sold liquor from flasks tucked into their boots. The term “rum-running” most likely originated at the start of Prohibition, when ships from the Caribbean transported rum to Florida speakeasies. Rum’s cheapness made it a low-profit item so smugglers switched to shipping Canadian whisky, French champagne, and English gin to major cities like New York City, Boston, and Chicago, where they could charge more. Ships carried as much as $200,000 in contraband in a single run.
