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An old slang term for a detective or [investigator] (police-affiliated or private). Variants include "dick" or "[private dick]," the connotations of which were not meant to be obscene. Shoes in the late 1800s were made of gum rubber - the soft-soled precursors of the modern sneaker. The phrase "to gumshoe" meant to sneak around quietly as if wearing gumshoes. "Gumshoe man" was [originally] slang for "thief," but by about 1908 the term "gumshoe" was used to refer to a police detective, and the term has stuck ever since (pun intended).
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