Wide boy is a British term for a man who lives by his wits, wheeling and dealing. According to the Oxford English Dictionary it is synonymous with spiv. The word "wide" used in this sense means wide-awake or sharp-witted. Newspapers of the late 1940s and 1950s often use both terms in the same article about the same person when dealing with ticket touts, fraudsters and black market traders. It has become more generally used to describe a dishonest trader or a petty criminal who works by guile rather than force.
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An early use of the term was in the 1933 film "Friday the Thirteenth", where the character played by Max Miller, a loud, quick-witted, Cockney market trader, is heard to say "I'm the widest boy ever put on a pair of shoes!"
The term came to public attention in 1937 with the publication of Wide Boys Never Work by Robert Westerby, a novel about gamblers and hustlers. During World War II such individuals became involved in the black market, but the term only began to appear in newspapers from 1947.
Fictional portrayals
Fictional wheeler-dealer Cockney characters such as Del Boy from Only Fools and Horses, Frank Butcher from "EastEnders", Private Walker from Dad's Army, Arthur Daley from Minder, Mike from The Young Ones, Harry Robinson from The Ladykillers, and Flash Harry from the St Trinian's films, all exemplify various wide boy "types".
Other usage
"Wide boys" is used humorously but now commonly to refer to wingers in Association, Gaelic or Rugby Football.