What does wiliest mean?
Wiliest is the standard superlative of the adjective wily, meaning cunning, crafty, or skilled at devising deceptive schemes. It identifies someone as more cunning or crafty than anyone else in a group. The word is often used in stories, fables, descriptions of political maneuvering, and humorous comparisons: one person may be called the wiliest negotiator, player, or fox. Unlike cleverest, which can mean intellectually quick or skilled, wiliest specifically emphasizes the ability to use deception, stratagem, or an insight into others' motives. Its literary or slightly playful tone makes it especially effective when naming a conspicuously calculating person, though it remains fully standard English. In less emphatic contexts, wily or cunning may be preferable. The form also illustrates the irregular comparison of a consonant-final y: wily becomes wilier and wiliest.
adjectiveThe superlative of wily: possessing or displaying the greatest degree of cunning or craft.
- Having more cunning or craft than anyone else; the most wily.
"The wiliest strategist was the one no opponent suspected would move at all."
"The wiliest strategist was the one no opponent suspected would move at all."
"Her grandmother called him the wiliest negotiator in the family."
Wiliest marks the apex of cunning: where most people plot, the wiliest plots back.
Reviewed by Deb Chak, Editor. AI-assisted content curated by RJS Tech Solutions LLP.
Etymology of wiliest
Wiliest is the superlative of wily, an adjective descended from Old English wīl, meaning "cunning" or "craft." That Old English word is related to wile and will, reflecting a Germanic root associated with intention or cunning. The English noun guile was borrowed from Old French but is likewise cognate with wile and wily through the same Germanic ancestry.
Related word forms
How wiliest is actually used
This superlative is standard but less common in neutral prose than wily. It often has a literary, dramatic, or humorous tone and is especially natural in phrases that identify one person as the cleverest or most cunning among a group.
Easily confused with wiliest
Wilily is an adverb meaning "in a cunning or crafty manner," whereas wiliest is the superlative adjective meaning "most cunning."