Cunning occupies a charged and ambivalent position across the depth-psychological corpus. It is never simply a cognitive skill; it functions as a marker of psychic quality — the intelligence of the serpent, the trickster, and the heroic underdog — and its moral valence shifts dramatically depending on who wields it and against what. Jung identifies it as an attribute of both the heart's knowledge and the chthonic unconscious: a cunning heart yields cunning understanding, just as a good heart yields goodness. In Radin's analysis of the Trickster cycle, cunning is the constitutive faculty of the figure who exists prior to moral differentiation, belonging neither to wisdom nor to simple animality but inhabiting their unstable threshold. Kerenyi and Rank read it into the mythic topology of Troy and Pandora — fortresses and traps penetrable only through guile, symbols of the maternal enclosure that culture must outwit rather than overpower. Hillman inverts the giant/cunning-creature opposition to make cunning the faculty of imagination against literalism. The Chinese classical tradition, mediated through Wang Bi, associates cunning with the falsifying distortion of desire, contrasting it with authentic spontaneity. Hoeller's reading of the Gnostic serpent presents cunning as the ambiguous instrument by which the deep brings forth both poison and illumination. Across these positions, cunning names the intelligence of the marginal and the chthonic — indispensable, dangerous, and rarely domesticated.
From a cunning heart you will know cunning. From a good heart you will know goodness. So that your understanding becomes perfect, consider that your heart is both good and evil.
Jung argues that cunning is not an external cognitive capacity but a direct epistemological expression of the heart's own nature, placing it within the dual moral constitution of the psyche.
, The Red Book: Liber Novus, 2009thesis
The serpent descends into the deep and with her cunning she either paralyzes or stimulates the phallic demon. The serpent brings up from the deep the very cunning thoughts of
The Gnostic serpent's cunning is presented as the faculty that mediates between the chthonic depths and conscious life, functioning as both an inhibiting and an animating force.
, The Gnostic Jung and the Seven Sermons to the Dead, 1982thesis
his fondness for sly jokes and malicious pranks, his powers as a shape-shifter, his dual nature, half animal, half divine, his exposure to all kinds of tortures, and—last but not least—his approximation to the figure of a saviour.
Jung's commentary on the Trickster identifies cunning and roguery as constitutive of a figure whose psychic antiquity precedes ethical differentiation, linking the amoral intelligence of the trickster to the alchemical Mercurius.
, The Trickster: A Study in American Indian Mythology, 1956thesis
Troy itself, the im-pregnable, the innermost part of which one can reach only through cunning, is like every fortress a symbol of the mother.
Rank reads the cunning of the Trojan horse as an unconscious psychic strategy for re-entering and overcoming the maternal enclosure, making guile the instrument of individuation from the primal womb-symbol.
, The Trauma of Birth, 1924thesis
What qingwei tends to is the multifarious designs of cunning and deceit.
The Wang Bi commentary tradition treats cunning as the product of selfish desire distorting natural spontaneity, aligning it with falsehood that arises when 'wisdom' corrupts authentic being.
, The Classic of Changes: A New Translation of the I Ching as Interpreted by Wang Bi, 1994thesis
the giant is counterpoised in fairy tales with the cunning animal, the elf or gnome, the savvy maiden or the little tailor. These would never equate an acorn with a leaf blown by or a drop of dung.
Hillman valorizes cunning as the imaginative intelligence of small, marginal figures that resist the literalistic reductionism of the giant, making it the faculty through which soul perceives metaphor.
, The Soul's Code: In Search of Character and Calling, 1996supporting
whatever creatures you see breathing the air of life, their kind has from the start been preserved and protected by its cunning, its courage or its speed
The Hellenistic materialist tradition presents cunning as one of three foundational survival capacities alongside courage and speed, grounding it in biological rather than moral necessity.
, The Hellenistic Philosophers, 1987supporting
Heracles, in the guise of a trickster, is shown trying to lure his brother, who has taken refuge on the roof of the temple, down to him with a basket of fruit or some other kind of delicacy. The club is all too visible in his other hand.
Kerenyi observes that even the hero Heracles adopts trickster cunning — concealing violent intent beneath the guise of temptation — demonstrating the archaic fusion of heroic and roguish intelligence.
, The Trickster: A Study in American Indian Mythology, 1956supporting
All other kinds of wisdom or cleverness, which seem only, such as the wisdom of politicians, or the wisdom of the arts, are coarse and vulgar. The unrighteous man, or the sayer and doer of unholy things, had far better not be encouraged in the illusion that his roguery is clever
Plato distinguishes genuine wisdom from mere cleverness and cunning, arguing that those who mistake roguery for intelligence are self-deceived about what constitutes true knowledge.
, Theaetetus, -369supporting
In her breast Hermes planted lies, flatteries and treachery. The Messenger of the Gods furthermore gave her a voice, and named the woman Pandora
Kerenyi notes that Hermes installs deceptive cunning — lies, flattery, treachery — into Pandora at her creation, identifying trickster intelligence as a divine gift that is simultaneously a weapon against humanity.
, The Gods of the Greeks, 1951aside