One interesting question in Cuba's history is -Why did Cuba fail to become independent in the early part of the nineteenth century, at the same time as most countries in Latin America? Simple explanations such as slavery, economic conditions at the time or the special relation between Cuba and Spain are not very convincing by themselves. We present a framework recently developed for the analysis of democracies and we adapt it to the circumstances prevailing at the time in the first section of the paper. Subsequent sections used this adapted framework to gain new insights on the possible role of each of the factors mentioned previously in delaying Cuban independence and on the lack of a one-to-one relation between independence and democracy. That is, we consider in separate sections the special relation with Spain, the role of slavery, and the economic conditions at the time. A brief concluding section provides perspective on the answer to this question and on the relation between independence and democracy.