Academic researchers tend not to study dysfunctional, disturbing or malfeasant administrative and organizational behaviors in the higher education (HE) sector; yet, a variety troubling things regularly take place in HE. This article offers some 'conceptual spadework' to open up the muted discussion about this disquieting aspect of the sector. We defined these troubling acts and behaviors as maladministration, and describe the types of maladministration that occur in contemporary HE. Then, based on a narrative theoretical review of prominent scholarship in the organizational and leadership studies literatures, we outline a multi-level theoretical framework to help investigate and understand why maladministration emerges and persists in HE. The framework addresses the nature (personality traits, motives, values) of administrators who commit troubling acts, the predispositions of organizational members and the organizational cultures they constitute, and the broader institutional environment of globalized neoliberal, managerial and corporatist reforms that create the pressures, conditions and opportunities for maladministration. We illustrate this framework with an empirical case study of a high-profile failure of leadership in responding to reports of sexual abuse at a university in the USA, and conclude with implications of the framework for research and practice in HE.