This paper inspects the elusive divine involvement of politics in Geoffrey Chaucer’s Troilus and Criseyde, focussing on how the gods and goddesses vigorously trace the destiny of the insignificant lovers. Different from reflexive fantabulous and fabulous mythological records, goddesses such as Venus and Fortune exercise an enormous influence over human-emotion and decision-making, moulding hesitation on the independence of individual determination. By investigating supernatural manipulation and its emotional and political ramifications, the research investigates how Chaucer analyses the role of higher super-powers in shaping human and societal fates. Venus, representing the inconsistency and instability of love passion, and Fortune, demonstrating the unpredictable nature of earthly events, contribute to a tale formed by divine randomness and emotional softness. The consequent tension between predestination and free-will emphasizes Chaucer’s complex realization of love, fate, human and supernatural agency. Eventually, the poem propositions a clear deliberation on the boundaries of human control in a cosmos governed by heavenly impulse, revealing the comprehensive socio-political and supernatural consequences of such religious conceptions.