In response to the question of the relevance of ‘classical’ African Studies to the contemporary need of the continent, this article explores the dynamics of leadership challenge as portrayed in Yorùbá music drama genre, using Duro Ladipo’s most popular folk opera: Ọba Kòso (The king did not hang) as a case study. Thematic exploration of the opera was carried out to establish the linkages between leaders’ (characters’) traits and styles as portrayed in the play, and Nigeria’s political leaders’ engagement and responses to social contracts with their citizens. By comparing the outcomes of the actions, inactions and (in) decisions of Nigeria’s political leaders and the attendant consequences on their subjects with those found in the opera. I argue that the African political leadership challenge is shaped by a combination of complex factors, including the leaders’ charisma and the quality of citizens’ engagements in the affairs of governance. These are largely occasioned by multiple effects of torrential and irresistible mob pressures on leaders. At the fringes of the debacle is a convergence of human fate and other coincidental elements within the various sites of the divide in the contestation for and utilization of power as a whole.