The word first appeared in the 1850s in Maine and of course it refers to smuggling liquor. But this seemed odd to me because Prohibition didn’t start until almost 70 years later. That is, except in Maine, the first dry state, where it became illegal to manufacture or consume liquor in 1851. Because Maine shares a border with Canada, the law was easily flouted. Ordinary folks wanting to smuggle liquor into the country could hide a couple bottles in their pants legs in Canada and walk into the United States.
(Don’t jump to any conclusions about that pattern on the floor–before Hitler took the swastika for his Nazi Party, it was a perfectly respectable symbol dating from ancient times that was often used to decorate mosaics, tiles, pottery, and other items. This photo pre-dates the Nazis.)
Mary Miley's Roaring Twenties 
The term originated in the 1850’s long before prohibition because it had nothing to do with prohibition itself. The term bootlegger was brought on when selling liquor to Indians became illegal in 1851. Cowboys would smuggle the flat liquor bottles in their boots to sell or trade with the Indians. Henceforth “bootlegger.”
Good story. Can you document that?
Saw a documentary about prohibition which stated it came from people who would smuggle alcohol in bottles strapped to their lower leg for which they would charge others for a small amount of it to drink. I don’t know how they actually dispensed it ….?
The term bootlegger originates from the late 1700’s in Cornwall. After the United Statsian war of independence the United Kingdom was in near financial ruin. Taxes rose enormously to pay for the conflict and that caused the fishing industry and other industries to collapse in Cornwall. The locals turned to smuggling from France (salt, textiles and alcohol). Cornish smuggling evolved into an enormous business with hundreds of people involved at any one coastal village. Division of labour amongst the smuggling community resulted in the evolution of roles such as “Batsmen” (armed men to fight the Revenue Men), “Barrel men” (carrying contraband up from the beaches to the caches) and the “Bootleggers” (distribution men, hiding contraband in their long baggy sea boots)
Good story. Can you document that?
Errr…. its not a ‘story’. The History of smuggling and wrecking along the Dorset, Devon and Cornish coast is immensely well documented. As to the core premise that “bootlegger” originates to that period, that comes from documentation in Polperro smuggling museum. I have been searching for an easy online (credible) reference. I fear I will have to go to the local library. If it is any comfort to you, I live in Dorset 2 miles from the coast. There are at least 2 pubs called the Smugglers within a few miles of me, one coast path called the Smugglers Track (up White Nothe into the hinterland away from the beach) and several Smugglers Coves. These are 200-300 year old smuggling ‘artifacts’, they are not named like that for contrived effect.
Sorry, I didn’t mean “story” to sound like fiction. I meant, it’s an interesting story, and I realize smuggling and the southwest coast go back a long ways, but there are other stories as to the origin of the word bootlegger as well, and I’m just wondering if you have some documentation to prove that this was indeed the origin of the word, rather than one of many instances where it was used. (See some claims above.) Next time I’m at the public library, I’ll check the Oxford English Dictionary.
I am quite happy to walk back from using the word ‘origin’. The evidence in Polperro museum is probably more accurately labelled the ‘earliest’ use of the word ‘bootlegger’ (that I have found so far).
Let me dig around some of the local libraries, see if I can pin this down.
I’ve found newspaper articles with the term “boot-legs” as far back as the 17th century regarding the actual clothing attire. As far as why bootleg is tied with liquor is obvious (hiding flasks in “boot-legs” etc)… Also, many other states also had “dry laws” in the mid 1800’s. Which is subsequently the earliest I’ve been able to find documentation on the word in the liquor smuggling sense.
And we still have “bootleg” style on jeans and other slacks today, so they fit over boots.
It all makes sense to me. Boots haven’t changed all that much. We bootleg half pints into college football games all the time. I didn’t realize I was part of such great history!!!!!
Some around here have said that “bootleg” originated during the 1880s-90s when at that time there was a border between Oklahoma Territory and Indian Territory until statehood in 1907. Since Indian Territory was “dry” and until statehood when they combined, Oklahoma Territory was not. Saloons lined the border and so draw obvious conclusions. But I personally have always believed the phrase was around much before then and basically meant the same thing.