Glossary entry
Wiseguy
WYZE-gy
Definition
WYZE-gy
A member of the life, used loosely of both made men and the associates who work alongside them. Within the organisation it is plain description; from outside it is an insult.
“He had been around wiseguys since he was thirteen and had never once considered doing anything else.”
The word carries a deliberate note of irony — the wise guy who knows how things really work, who has seen behind the arrangement everyone else believes in.
Nicholas Pileggi used it as the title of his 1985 book on Henry Hill, which became Goodfellas, and that pairing fixed the sense in which most people now use it: not a rank, but a way of living.