The earliest use of the term bootlegger occurred in the Midwest in the 1880s, when people would conceal flasks of liquor in their boot tops when going to trade with Native Americans.
The term became more permanent when Congress passed Prohibition in 1920. Now illegal (until the amendment’s repeal in 1933), alcohol was smuggled into the states from Canada and Mexico by bootleggers, who later secretly distilled their own liquor. Terms including “rum runner” and “moonshine” also became popular around the same time. So choose your poison and say cheers to those who worked hard to drink hard back in the day.