This dissertation examines the colonial factors contributed to surprisingly high levels of social development and postcolonial democracy in the West Indies vis-ÌÊ-vis Sub-Saharan Africa. I develop a hypothesis that distinguishes between forced settlement (i.e. the import of non-indigenous slaves and/or indentured laborers to newly settled territories) vs. colonial occupation (i.e. European domination over indigenous societies, and the reorganization of these societies into modern states) as the modal forms of colonization in each region. I argue that the superior developmental outcomes associated with forced settlement vis-ÌÊ-vis colonial occupation are the consequence of specific social, political and administrative reforms introduced following the abolition of slavery, when the colonial state was reorganized along metropolitan lines, and emancipated slaves were legally reconstituted as citizens or subjects of the metropolitan state. In colonies of occupation, by contrast, state power was bifurcated: there were distinct legal-administrative institutions for indigenous vs. non-indigneous populations, as the indigenous majority was generally denied metropolitan citizenship, and subjected them to harsh and arbitrary forms of justice and compulsory labor, which persisted until after the Second World War. Consequently, civil law remains weakly institutionalized in these societies, which gained independence with low levels of social development, and have struggled to maintain democratic rule after independence. This argument not only explains the superior postcolonial development outcomes in the West Indies vis-ÌÊ-vis Sub-Saharan Africa, but it also explains why African states colonized by forced settlement (e.g. Mauritius, R union, Seychelles, Cape Verde, São Tom & Principe) have experienced patterns of development and political regime outcomes that are broadly similar to those of the West Indies.  The dissertation follows a multi-method approach: First, I use statistical analysis to examine the long-term consequences of each mode of colonization on education attainment (1950 to 2008) and political regime outcomes (1946-2004) across countries and territories decolonized after World War Two. Second, I use comparative historical analysis to elucidate the causal mechanisms that link each mode of colonization to specific developmental and regime outcomes across pairs of former British and Portuguese colonies in the West Indies and Sub-Saharan Africa: Jamaica and Ghana, Cape Verde and Guinea-Bissau.