This article highlights one likely ‘fall’ to which Catholic education is susceptible in the modern era due to the oppressive climate in which it operates. Our critical method in arguing for this position is to oscillate between two texts—one written and one visual: Genesis 3: 1–18 and Masaccio’s painting of ‘The Expulsion’. The hope is that one will inform and enrich a deeper understanding of the other. As part of this exercise in creative hermeneutics, we first argue that the dramatic story of the fall through pride or amor sui (self-love) and its resultant feeling of shame is a universal one in which readers (listeners) glimpse the long history of their own fears and desires. Second, we show how one 15th century Italian painter represented the tragic consequences of the Faustian self by examining Masaccio’s painting in some detail. Third, we investigate St. Augustine’s writings on this narrative and suggest how some forms of self-elevation align dangerously with the promotion of the autonomous self in contemporary education. We also critically examine exegetical writings from Jewish and Christian perspectives to draw out further meanings of the narrative. Fourth, we point to the themes of hiding and forgiveness embedded in the account which leads us neatly into the last fifth section where we discuss the text’s implications for contemporary Catholic education. Here, the focus is on one likely ‘fall’ of Catholic education when it fails to live up to its distinctive mission to place love unconditionally at its centre. In a highly market-driven, managerial climate of competition where league tables, bureaucratisation, and data analysis assume an overwhelming significance allied to institutional survival and kudos, the temptation is to show the worth of the school by emphasising its examination success and employment rates rather than through its service to others, especially those who have been forgotten. Although we are highly sensitive to the conflictual demands on Catholic institutions at the present time from a variety of stakeholders, we conclude that their healthy continuation depends on their public, ethical avowal to love everyone unreservedly with assistance from God’s grace and when this aspiration fails, to seek forgiveness. The article is not concerned with strategies of resistance against those developments in education contrary to a Catholic philosophy.