What does cunningest mean?
Cunningest is the superlative form of the adjective cunning, describing someone or something as possessing the greatest degree of craftiness, slyness, or clever ingenuity. A person called the cunningest of their group is seen as exceptionally adept at getting what they want, whether through wily deception or sheer mental agility. The word carries a dual character: it can express grudging admiration for sharp wit — as when a folk hero outsmarts every rival — or signal distrust of someone too artful to be trusted. It appears most often in informal speech, literature, and especially traditional tales about tricksters such as Reynard the Fox or Anansi the Spider, where ranking characters by their craftiness is part of the fun. Less common than "most cunning," the single-word superlative lends a slightly archaic, storybook flavour to prose. Its roots reach back to Old English, where the underlying verb simply meant to know — a reminder that, at heart, cunning has always been knowledge applied with intent.
adjectiveSuperlative form of "cunning": most skilled at achieving one's aims by deceit or clever ingenuity; most crafty or sly.
- Most crafty or sly; superlative of cunning (skilled at deceit).
- Most clever or ingeniously skilful (a milder, non-deceptive sense).
"The fox in the old fable is surely the cunningest creature in the forest."
"Everyone agreed the old fisherman was the cunningest trader in the village market."
"Of all the tricksters in folklore, Anansi is often called the cunningest of them all."
The superlative of "cunning" comes from an Old English verb that simply meant "to know" — so the cunningest person was originally just the one who knew the most.
Reviewed by Deb Chak, Editor. AI-assisted content curated by RJS Tech Solutions LLP.
Etymology of cunningest
Cunningest derives from cunning, which descends from the Old English verb cunnan, meaning "to know" or "to know how." In Middle English, present participles like "cunninge" came to denote knowledge or skill generally before narrowing toward craftiness and deceit. The superlative suffix -est is a native Germanic formation, giving the word its familiar English pattern. Cognates sharing this ancient Germanic root include "can" and the Scots "ken," both also meaning to know or be able.
Word family
Usage notes
Informal to literary in register. The superlative form is less common than "most cunning" and tends to appear in storytelling, folk tales, and playful or colloquial contexts. Connotations range from admiration for shrewd intelligence to disapproval of deceitfulness, depending on context.
Don't confuse with
"Conning" means swindling or steering a ship, while "cunningest" is the superlative adjective meaning most crafty.