Bootleg

Nothing to declare.

Dear Word Detective:  What is the origin of the word “bootleg,” as in illegally sold liquor? — Nic Roberts.

That’s a good question.  Incidentally, an apology is due to all those readers who have written in with this question over the past few years.  I assumed that you had simply neglected to check our archives, because I knew for a fact that I had explained “bootleg” years ago.  And, indeed, I had.  Unfortunately, I had explained it in a entirely different column I used to write for the New York Daily News.  Oops.  Another instance of creeping enfeebleation, I guess.  Actually, I don’t think my mind was any sharper when I was younger.  I just had far less to remember.

You mention liquor in your question, and it is true that the earliest use of “bootleg” in the sense of “contraband” was with regard to alcoholic beverages that were, at the time, illegal in some place for whatever reason.  Most uses of “bootleg” in the news today, however, refer to “bootleg DVDs” or “bootleg music files,” and I know that I first became familiar with the term in the late 1960s when “bootleg” tapes of Bob Dylan’s recording sessions were a hot item.  Of course, forbidden fruit is a staple of the human diet, and I’m sure that if you went back far enough, you’d find “bootleg” scrolls being sold on the streets of Babylon.

But the term “bootleg” itself is, in the “contraband” sense, actually a surprisingly recent arrival, first found in print in the late 1800s.  “Bootleg” had been used up until that point simply to mean “the upper part of a tall boot.”  But even in this earlier literal use there were hints of the later sense of “bootleg” to mean “smuggled contraband.”  Such tall boots provided a handy hiding place for a gun or knife slipped between the boot and leg (“He … paused only to slip into his long boot-leg a ‘shootin’ iron,’ 1889).  In “dry” communities, the “bootleg” also served as a handy hiding place for a flask of liquor (“There is as much whisky consumed in Iowa now as there was before, …’for medical purposes only,’ and on the boot-leg plan,” 1889).

The use of “bootleg” to mean something literally carried in one’s boot to avoid detection was quickly generalized to mean anything surreptitiously transported, sold or possessed.  The term spread widely during Prohibition (1920-1933) in the United States, when production and possession of alcoholic beverages was outlawed by the 18th Amendment to the US Constitution  and “bootlegging” liquor became a big business.

Today “bootleg” is applied to just about anything illicitly sold, from “black market” software to untaxed cigarettes to cosmetic procedures conducted in unlicensed storefront clinics.  Interestingly, “bootleg” is almost always used to describe something for which a legal equivalent exists.  Thus we speak of “bootleg” pharmaceutical drugs or “Happy Feet” DVDs, but not “bootleg” heroin or hand grenades.

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