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June 11, 1996
Thomas Willshire writes: I've heard of bootleg gin, bootleg records, and the play a quarterback runs in the NFL called a bootleg. The latter is a play designed to deceive the opposition. These uses of the term all carry some suggestion of phoniness or inauthenticity. OK. What does that have to do with a boot and a leg? The original meaning of bootleg in the seventeenth century was a rather boring one: 'the upper part of a boot'. It becomes relevant to your senses when people began to smuggle liquor by hiding the hooch in their boots. (Strange as this may seem, it was apparently a real practice in the late nineteenth century.)
Rather than "phoniness or inauthenticity," as you suggest, the main meaning is something like 'illegal; unauthorized; unregulated'. In early use, around 1890, this was usually referring to liquor, with "bootleg" as a noun being more-or-less equivalent to moonshine, and as a verb meaning 'to smuggle liquor'. The broader application to anything smuggled or made illicitly, such as bootleg cigarettes or a bootleg recording, arose by the 1920s. Still later senses, such as the bootleg play, which was in use by the 1940s, bring the idea of simple deception to bear.
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