Public diplomacy is discursively focused on enhancing global influence, epitomized in Nye’s theory of soft power. Most countries desire soft power. The exception is one form of governance: authoritarianism. Autocrats have a complex relationship with soft power. The significance of understanding these dynamics is enhanced by the rise of ‘strongmen’ populists. The chapter outlines an interdisciplinary conceptual model, drawing inspiration from Greek mythology. Cassandra, a daughter of Priam, King of Troy, predicted Troy would fall, but was dismissed. ‘Cassandra Syndrome’ is a metaphor to describe someone whose valid warnings are disbelieved. For every ‘Cassandra,’ an analyst whose warnings are dismissed, there is a ‘Priam,’ a leader who fails to listen. The chapter therefore explores the dynamics of a ‘Priam Syndrome’—a constellation of structural, psychosocial, and discursive factors enabling destructive, authoritarian leadership leading to soft power decline.