Where would the Ask Yahoo! team be without Michael Quinion's expansive and erudite World Wide Words site? Probably skulking around in bleak online dictionaries, missing the charm and humor of an eloquent word enthusiast. Mr. Quinion, with the help of his trusty Oxford English Dictionary, finds the first use of the phrase in the Omaha Herald in 1889: There is as much whisky consumed in Iowa now as there was before..."for medical purposes only," and on the boot-leg plan. A bootleg refers to the long leather boots worn by cowboys in the Old West. They were used to store all manner of illicit goods, including an extra gun, a bowie knife, or a flask of
moonshine. Incidentally, a bootleg play in football refers to quarterback running pattern that entails making a sharp perpendicular turn around the tight end. Over at Random House, the Maven's Word of the Day notes the phrase's surge in popularity during the Prohibition Era. It's now used to refer to anything illegal, unauthorized, and unregulated, like concert recordings.
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