Self-esteem occupies a contested and richly layered position across the depth-psychology corpus. Far from functioning as a simple measure of positive regard toward oneself, the literature reveals it as a site of profound ambivalence: at once a genuine developmental achievement grounded in early attachment and parental attunement, and a potential vehicle for narcissistic inflation, other-dependency, and spiritual deformation. Kohut’s self-psychology, mediated through Flores, identifies healthy self-esteem as the product of age-appropriate mirroring and idealization — its absence leaving individuals chronically vulnerable to shame, rejection, and addictive substitutes. Berger, drawing on Schnarch and Bowen, introduces the crucial distinction between ‘other-validated’ and self-supported esteem, arguing that externally contingent self-worth generates emotional reactivity and arrested differentiation. Schore locates self-esteem neurobiologically, linking it to superego development and the regulatory oscillation between shame and pride. Against these constructive frameworks, McGilchrist and Hollis levy a trenchant critique: the modern ‘cult of self-esteem’ too frequently masks narcissistic emptiness, and Baumeister’s own reversal of his earlier advocacy confirms that unconditional self-esteem fails to deliver on its promises. The Philokalia introduces an ascetic counter-discourse, treating self-esteem as a passional vice — a subtle demonic temptation undermining the spiritual soldier. This tension between self-esteem as psychological necessity and as spiritual or characterological hazard gives the concept its enduring analytic interest.