In 1919 the US adopted the 18th Amendment to the Constitution, banning the manufacture and sale of alcohol. It was generally known as “Prohibition.” In 1933, after reviewing the mostly disastrous results (enormous growth in organized crime, for one), the whole thing was repealed. But it left some traces behind in language. The most widely used word popularized by the Prohibition era is probably “bootleg.”
“Boot legs,” of course, have been around since people first started wearing high-topped boots. The term appeared as early as 1634: “For a payre of Boot-legges needfull to be used …” It wasn’t used as a term meaning something hidden, though, until about the 1850s: “…if you will take a look into his right bootleg, we should say that a serviceable bowie-knife might be found.”
Many things could be hidden in the leg of a high boot, and by the late 1800s everybody assumed that whatever was hidden was illicit in some way. Alcohol was banned in many US localities even before the 18th Amendment, and by 1889 “bootleg” was a reference to any liquor you weren’t supposed to have: “There is as much whisky consumed in Iowa now as there was before,..‘for medical purposes only’, and on the boot-leg plan.” Then when Prohibition was in full swing, “bootleg” entered the language in a major way: “Gradually I’m becoming acquainted with all the brands of bootleg that the West coast offers” (Hart Crane, 1929).
It’s a bit of a puzzle why “bootleg” got so closely tied to illegal alcohol. After all, if you’re going to try to smuggle a glass bottle full of liquid, the leg of your boot doesn’t seem like the best hiding place. Nevertheless, “bootleg” was solidly entrenched as a term for illegal liquor. The 18th Amendment, by the way, didn’t just prohibit the sale of alcohol; it banned manufacture too. But people have been making alcohol for millennia; it’s not hard to do. There’s even a rule in the Code of Hammurabi from 1700 BCE about being fair in trading barley for beer. So “bootleg” — as well as “bathtub gin” — meant homemade as well as smuggled alcohol, even though you need a bit more equipment than just a bathtub.
After Prohibition ended, “bootleg” stuck around, and now means nearly any illicit product — particularly something with a faked label or brand, like a “bootleg Tesla battery” or a “bootleg Rolex watch.” As for actually using bootlegs for smuggling, well, it’s probably easier than ever since valuable loot nowadays might be as tiny as a microchip or SIM card. Those would even fit into a bootleg much better than a bottle of bathtub gin.
