This book examines the relationship between state size and the formation and maintenance of democratic political systems. Using a cross-national, multiple case study of The Gambia in West Africa, and Trinidad and Tobago in the Caribbean, in combination with a quantitative data set on all the nations in the world, the study examines the effects of smallness, when measured by population size, on a number of variables including the probability of becoming and remaining democratic, access to information, political instability and political violence. The dissertation argues that the small scale social structure which is prevalent in small states directly affects the social interaction of individuals in these states through the multiple-role relationships created as a consequence; and indirectly affects the political and economic systems of these states through the impact of such social networks on political interaction, etc. The case studies examine the effects of smallness on two states that, aside from being small and democratic, share few background characteristics. It is argued that small state size acts as an enabling environment for democratization, increasing the likelihood that such states will become and remain democratic, as occurred in Trinidad and Tobago. The case of The Gambia illustrates the limitations of smallness to overcome other obstacles to democratization including economic, social, and systemic limitations. The quantitative analysis establishes a significant statistical relationship between small state size, when measured by population, and the formation and maintenance of political democracy, and an increased likelihood of political violence, when measured by political riots and deaths by political violence. The analysis concludes with a discussion of the implications of such findings, including transferability through the application of targeted decentralization programs.