The modern academy is rediscovering what the modern world has never forgotten: the magnetism and multivalence of saints, those who are “holy” (sancti; hagioi). Holiness is a theological category, yet theological understanding orients personal behavior and validates institutional practices, extending its power deep into the realm of political existence. This dissertation investigates, first by way of an ethnographic case study of a Greek Orthodox community in Cyprus, and then through a critical analysis of key theological writings whereby an Orthodox paradigm of holiness was first threshed out and ultimately canonized, how holiness is mediated, that is, inscribed and mobilized in human societies by way of the saints, the array of material media that represent them, and the psychosocial processes of identification, interpretation, and communication by which their influence is digested locally. I argue that the many means of mediating holiness at work in Orthodox communities and their intercultural milieux constitute a lived theology of struggle with cultural, political, and religious configurations that are perceived/constructed as anti-Orthodox. Such theology—formally and informally enunciated (or indeed tacit), embedded in a wide range of media and practices—can be identified as an enduring current in Orthodox self- and other-understanding. The mediation of holiness continues to warrant and enact all manner of resistance where Greek church communities experience themselves as subjugated, but the pattern was scripted already in antiquity: it was strategically vital to the formation of the Orthodox theological paradigm in which materiality, sensuality, and imagination are indispensable to the salvation and sanctification of human beings.