Chapter 6 surveys Haiti’s colonial experiences in the context of the glaring inequity in the distribution of national wealth, a legacy of autocratic and despotic rule as well as Haiti’s persistent internal socio-economic strife and disruptive political feuds in the context of the geostrategic interests of the United States in the region. The author traces the election of Jean-Bertrand Aristide to the presidency in December 1990 on a socialist platform to tackle economic inequality and social injustice, a political crisis (2000–04) stemming from disputed parliamentary, local and presidential elections in 2000 and the refusal of the opposition, civil society and the international community to endorse them as well as regional/multilateral efforts and mechanisms to resolve it peacefully. Political dissent and an armed rebellion made the country virtually ungovernable. Ultimately, geopolitical apprehensions over Aristide’s ideological drift and political alliances in the Caribbean Basin caused local and foreign interests to exploit his democratic lapses as well as his autocratic tendencies and their leverage over Haiti to put an end to his presidency on February 29, 2004.