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Originally, gumshoe referred to a shoe with a rubber sole, specifically, galoshes or (more relevant to our purposes) sneakers. The senses of gumshoe leading to the 'private detective' sense all have to do with the idea that rubber-soled shoes give the wearer the ability to walk stealthily. http://www.randomhouse.com/wotd/index.pperl?date=19981110
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