The word bootleg (anything that is not strictly legitimate like alcohol or a load of CDs off a market stall and sold at a lower price than recommended), comes from the time of smuggling in places like Cornwall, when the smugglers wore large boots and hid bottles of alcohol(which they just happened to pilfer by nefarious means) literally in their boots, hence known as bootleggers, to get past the customs of the time. Nowadays it is anything gained by criminal means from said market stall to a robbery from a lorry like alcohol or cigarettes, and also illegal downloads of music, films etc.
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