This book explores Haiti's tumultuous political landscape, delving into socio-political and cultural elements that have shaped the nation's destiny. Utilizing an interdisciplinary approach, the book analyzes Haiti's underdevelopment across three critical epochs: from a former colonial territory to a singular independent nation amid colonial territories, and its constant quagmire due to foreign military interventions, notably from the United States. The narrative unearths Haiti's vulnerability, expertly analyzing focal points, both internal and external, that shed light on the perceived ineptitude of the Haitian political class. Furthermore, the book sheds light on institutional factors sustaining political instability, revealing how ineffectual leaderships have manipulated repressive and malversive tactics to maintain power, exacerbating the nation's structural vulnerability. Using concepts such as structural vulnerability, heterodoxicality, macoutization, demounization, and political barons, the author shines a spotlight on cultural elements and socio-political modes that have perpetuated Haiti's dysfunctionality. Employing a dialectical analysis through a critical and analytic lens, the book illuminates the multifaceted aspects of Haiti's enduring quest for democracy and the perpetual conflict it faces. Drawing from an impressive array of renowned scholars, this work enriches the conversation surrounding Haiti's political landscape, adding depth to the discourse, and, through its analysis, the book transcends traditional Haitianist and Caribbeanist dialogues and paves the way for a transformative understanding of Haiti's complex political landscape.