Résumé : Digitalization, that is, organizational renewal through new information and communication technologies, has long been invested with a fantasmic logic of affording alternative organizational ideals – democratic and not-for-profit rather than hierarchical and for-profit. Responding to calls to study the darker side of Silicon Valley inspired utopia, this paper investigates how and when organizational work on digitalization fantasies undermines organizational ideal renewal. In particular, this paper draws on the extended case of Alternative Bank (1963–2019) to shed light on how the long-term co-evolution of fantasy sublogics and power types in successive digital transformation projects induces organizational ideal reversal. I provide a theoretical model of how organizational ideal reversal comes about through the co-evolutionary conditioning of ‘have your cake and eat it’ affordances, mimetic neglect of real ethical affordances, and structural transgression of the ideal in the name of market and technical discipline. Ideal reversal occurs through consecutive phases of unwitting ideal transgression, followed by increasingly cynical and instrumentalizing transgression, and finally a cathartic moment of liberating ideal reversal. I advance several theoretical propositions on how digital fantasy work induces organizational ideal reversal, situating the dark side of fantasy work within a larger societal critique.