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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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