This study examines the transformation of human freedom from the Enlightenment to the digital age, arguing that modern autonomy has evolved into a sophisticated form of subjugation through disciplinary, biopolitical, and algorithmic mechanisms. Drawing on Kant, Nietzsche, Foucault, Butler, and contemporary critical theorists, the work analyzes how subjectivity is produced and governed within technological systems of power. It then proposes an alternative anthropological horizon through the Orthodox concept of personhood and the notion of theosis, understood not as mysticism but as an ontological mode of relational freedom. By integrating genealogy of power with theological ontology, the study advances the thesis that political liberation alone is insufficient in the age of digital governance and that genuine freedom requires a transformation of the human mode of existence itself.