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Although he has been at the hub of the emergence of a new mode of governance in Nigeria over the past two decades, scholarly analysis of the career of Chief Lamidi Ariyibi Adedibu remains surprisingly scant. In correcting this oversight in the literature, this paper uses the personal and political trajectories of Chief Adedibu as a point of departure for a broader contemporary sociology of Nigerian politics. In placing Adedibu within a nuanced context of “local” and “national” politics, it addresses key analytical dilemmas with obvious continental resonances: the emergence and continued success of “Big Men” in Nigerian (African) politics; the social, cultural, and (para-) legal conditions that facilitate their tenacity and longevity; and what their survival suggests about the futures of political neopatrimonialism in African societies.